- AN EFFICIENT ROUTE TO HETEROARENE-SUBSTITUTED VINYL- AND ALLYL-SILANES VIA PALLADIUM-PHOSPHINE COMPLEX CATALYZED CROSS-COUPLING
-
Heteroarene-substituted vinyl- and allyl-silanes were obtained in good yields by the cross-coupling reaction of either heteroaryl Grignard reagents with halovinyl- and haloallyl-silanes or, alternatively, silyl- and silylmethyl-substituted vinylmetallic reagents with heteroaryl halides in the presence of PdCl2(dppb) as a catalyst.
- Minato, Akio,Suzuki, Keizo
-
-
Read Online
- Synthesis of 6-thienyl-substituted 2-amino-3-cyanopyridines
-
An efficient method for the synthesis of 6-thienyl-substituted 2-amino-3-cyanopyridines by the ring transformation in the corresponding pyrimidines was developed. Further modification of the pyridines obtained under conditions of a room temperature aerobic Suzuki reaction in the presence of trans-bis(dicyclohexylamine)palladium(II) acetate as a catalyst was studied
- Verbitskiy,Cheprakova,Pervova,Danagulyan,Rusinov,Chupakhin,Charushin
-
-
Read Online
- Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites
-
The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had
- Ali, Wajid,Anjana, S. S.,Bhattacharya, Trisha,Chandrashekar, Hediyala B.,Goswami, Nupur,Guin, Srimanta,Maiti, Debabrata,Panda, Sanjib,Prakash, Gaurav,Saha, Argha,Sasmal, Sheuli,Sinha, Soumya Kumar
-
supporting information
p. 1929 - 1940
(2022/02/01)
-
- Photoelectric properties of aromatic triangular tri-palladium complexes and their catalytic applications in the Suzuki-Miyaura coupling reaction
-
The photoelectric properties and catalytic activities of substituted triphenylphosphine and sulfur/selenium ligand supported aromatic triangular tri-palladium complexes1-4, abbreviated as [Pd3]+, were investigated. The cyclic voltammogram of [Pd3]+in CH3CN-nBu4NPF6showed a single quasi-reversible wave which was consistent with their robust property and provided preliminary proof for their electron transfer processes in catalysis. With excitation at 267 nm, [Pd3]+exhibited strong ratiometric fluorescence at 550 and 780 nm at a temperature gradient from 77 K to 287 K. These peculiar triangular tri-palladium complexes showed excellent catalytic activities and exclusive reactivity with aryl iodides over the other halogenated aromatics in the Suzuki-Miyaura coupling reaction. The electronic and steric hindrance effects of substituents on the aryl iodides and aryl boronic acids including heteroaromatics like pyridine, pyrazine and thiophenes were explored and most substrates achieved up to 99% of yields. (2-[1,1′-Biphenyl]-2-ylbenzothiazole) which was analogous to the selective cyclooxygenase-2 (COX-2) inhibitors was also synthesized with our tri-palladium catalyst and gave good isolated yield (94%). The study of the catalytic process revealed that the mechanism of the reaction may involve the replacement of the sulphur ligand on [Pd3]+by iodine from aryl iodides, which was beneficial for the matching of C-I bond energy.
- Li, Jia,Li, Xujun,Liu, Xiang,Maestri, Giovanni,Malacria, Max,Wang, Xiaoshuang,Wang, Yanlan,Wu, Lingang
-
supporting information
p. 11834 - 11842
(2021/09/06)
-
- "benchtop" Biaryl Coupling Using Pd/Cu Cocatalysis: Application to the Synthesis of Conjugated Polymers
-
Typically, Suzuki couplings used in polymerizations are performed at raised temperatures in inert atmospheres. As a result, the synthesis of aromatic materials that utilize this chemistry often demands expensive and specialized equipment on an industrial scale. Herein, we describe a bimetallic methodology that exploits the distinct reactivities of palladium and copper to perform high yielding aryl-aryl dimerizations and polymerizations that can be performed on a benchtop under ambient conditions. These couplings are facile and can be performed by simple mixing in the open vessel. To demonstrate the utility of this method in the context of polymer synthesis: polyfluorene, polycarbazole, polysilafluorene, and poly(6,12-dihydro-dithienoindacenodithiophene) were created at ambient temperature and open to air.
- Minus, Matthew B.,Moor, Sarah R.,Pary, Fathima F.,Nirmani,Chwatko, Malgorzata,Okeke, Brandon,Singleton, Josh E.,Nelson, Toby L.,Lynd, Nathaniel A.,Anslyn, Eric V.
-
supporting information
p. 2873 - 2877
(2021/05/05)
-
- Three-dimensional covalent organic frameworks based on a π-conjugated tetrahedral node
-
The construction of three-dimensional (3D) covalent organic frameworks (COFs), especially fully conjugated 3D COFs, is a long-standing challenge. Herein, we report a saddle-like, π-conjugated cyclooctatetrathiophene (COTh) as a tetrahedral node to construct fully conjugated 3D COFs. The present work enriches the structural diversities and potential applications of 3D COFs.
- Gu, Zhangjie,Shan, Zhen,Wang, Jinjian,Wu, Miaomiao,Wu, Xiaowei,Xu, Bingqing,Zhang, Gen
-
supporting information
p. 10379 - 10382
(2021/10/12)
-
- Green-Synthesized Nickel Nanoparticles on Reduced Graphene Oxide as an Active and Selective Catalyst for Suzuki and Glaser-Hay Coupling Reactions
-
A mild and benign methodology to syntheses biaryls and 1,3-diynes has been demonstrated using the nickel nanoparticles supported on reduced graphene oxide (RGO-Ni) as a heterogeneous catalyst which is prepared using green reagents. A series of substituted biaryls and 1,3-diynes has been synthesised in good to excellent yields through C-C homocoupling reaction of arylboronic acids and terminal alkynes respectively using 1,4-dioxane as a benign solvent. The present ligand-free catalytic system proceeds smoothly under mild conditions, avoids noble and stoichiometric metal reagents and tolerates sensitive functional groups. Also has a wide substrate scope and feasible with other nitrogen and sulphur containing heteroaryl boronic acids. Hot filtration test unambiguously proves the true heterogeneity of the catalyst and which support for the further reusability of the catalyst for several times without any change in the activity. The easy preparation and simple magnetic separation, stability and reusability reveal that as-prepared RGO-Ni as a versatile catalyst for the synthesis of polyaromatic compounds both in academia and industries. Highlights: Green-synthesized RGO-Ni nanocomposite used as a heterogeneous catalyst for Suzuki type (C-C) and Glaser–Hay (C ≡ C) homocoupling coupling reactions. Ligand-free catalytic system and avoids noble and stoichiometric metal reagents Short reaction time with a minimum catalyst (nickel) loading RGO-Ni nanocomposite is highly stable, reusable, and magnetically retrievable.
- Murugan, Karthik,Nainamalai, Devarajan,Kanagaraj, Pavithara,Nagappan, Saravana Ganesan,Palaniswamy, Suresh
-
-
- Self-assembly of catalytically active supramolecular coordination compounds within metal?organic frameworks
-
Supramolecular coordination compounds (SCCs) represent the power of coordination chemistry methodologies to self-assemble discrete architectures with targeted properties. SCCs are generally synthesized in solution, with isolated fully coordinated metal atoms as structural nodes, thus severely limited as metal-based catalysts. Metal?organic frameworks (MOFs) show unique features to act as chemical nanoreactors for the in situ synthesis and stabilization of otherwise not accessible functional species. Here, we present the self-assembly of PdII SCCs within the confined space of a pre-formed MOF (SCCs@MOF) and its post-assembly metalation to give a PdII?AuIII supramolecular assembly, crystallography underpinned. These SCCs@MOFs catalyze the coupling of boronic acids and/or alkynes, representative multi-site metal-catalyzed reactions in which traditional SCCs tend to decompose, and retain their structural integrity as a consequence of the synergetic hybridization between SCCs and MOFs. These results open new avenues in both the synthesis of novel SCCs and their use in heterogeneous metal-based supramolecular catalysis.
- Adam, Rosa,Mon, Marta,Greco, Rossella,Kalinke, Lucas H.G.,Vidal-Moya, Alejandro,Fernandez, Antonio,Winpenny, Richard E.P.,Domenech-Carbo, Antonio,Leyva-Perez, Antonio,Armentano, Donatella,Pardo, Emilio,Ferrando-Soria, Jesus
-
supporting information
p. 10350 - 10360
(2019/08/20)
-
- Self-Assembly of Catalytically Active Supramolecular Coordination Compounds within Metal-Organic Frameworks
-
Supramolecular coordination compounds (SCCs) represent the power of coordination chemistry methodologies to self-assemble discrete architectures with targeted properties. SCCs are generally synthesized in solution, with isolated fully coordinated metal atoms as structural nodes, thus severely limited as metal-based catalysts. Metal-organic frameworks (MOFs) show unique features to act as chemical nanoreactors for the in situ synthesis and stabilization of otherwise not accessible functional species. Here, we present the self-assembly of PdII SCCs within the confined space of a pre-formed MOF (SCCs?MOF) and its post-assembly metalation to give a PdII-AuIII supramolecular assembly, crystallography underpinned. These SCCs?MOFs catalyze the coupling of boronic acids and/or alkynes, representative multi-site metal-catalyzed reactions in which traditional SCCs tend to decompose, and retain their structural integrity as a consequence of the synergetic hybridization between SCCs and MOFs. These results open new avenues in both the synthesis of novel SCCs and their use in heterogeneous metal-based supramolecular catalysis.
- Adam, Rosa,Mon, Marta,Greco, Rossella,Kalinke, Lucas H. G.,Vidal-Moya, Alejandro,Fernandez, Antonio,Winpenny, Richard E. P.,Doménech-Carbó, Antonio,Leyva-Pérez, Antonio,Armentano, Donatella,Pardo, Emilio,Ferrando-Soria, Jesús
-
supporting information
p. 10350 - 10360
(2019/08/27)
-
- Homocoupling of arylboronic acids catalyzed by dinuclear copper(I) complexes under mild conditions
-
An efficient protocol for C–C coupling has been developed using three iodo-bridged copper(I) complexes as catalysts. Complexes [CuI(bpy)]2 (1), [CuI(phen)]2·DMF (2), and [CuI(Mephen)]2 (3) were successfully synthesized via solvothermal method (bpy = 2,2′-dipyridyl, phen = 1,10-phenanthroline, and Mephen = 2,9-dimethylphenanthroline). The self-coupling reaction of phenylboronic acid was selected as a model reaction to evaluate the catalytic property of the complexes. Moreover, this method tolerates various substituents on the arylboronic acids such as halogens, carbonyls, and nitro groups. It shows that the iodo-bridged Cu(I) center serves as the active site to activate molecular oxygen during the catalytic process. The result illustrates that these complexes were found to be excellent catalysts for self-coupling of arylboronic acids under mild conditions.
- Long, Bing-Fan,Qin, Gui-Fang,Huang, Qin,Xiong, Ting,Mi, Yan,Hu, Fei-Long,Yin, Xian-Hong
-
p. 2639 - 2646
(2019/07/17)
-
- Synthesis of Sulfur-Hybridized Pyracylene and the Unexpected Phenyl Shift Mediated Rearrangement of Scholl Reaction
-
We present herein a strategy towards the straightforward synthesis of a novel sulfur-hybridized pyracylene, tetraceno[5,6-bc:11,12-b'c']dithiophene (TDT) derivatives, via 2-fold FeCl3-mediated Scholl reaction. Surprisingly, the substituents on the precursors will guide the synthetic route, when the substituents were bromo- or phenyl-, quantitatively debromination or phenyl ring shift mediated rearrangement were observed respectively, the rearrangement products were identified by the HR-Mass and 2D NMR analyses. Additionally, a retrosynthetic method was adopted to confirm the unexpected reaction results in rearrangement of Scholl reaction.
- Liu, Shuli,Huang, Chengting,Zhang, Jing,Tian, Siyu,Li, Chang,Fu, Nina,Wang, Lianhui,Zhao, Baomin,Huang, Wei
-
p. 3061 - 3070
(2019/05/22)
-
- Perfluorocyclopentadienyl Radical Derivative as an Organocatalyst for Oxidative Coupling of Aryl- and Thienylmagnesium Compounds under Atmospheric Oxygen
-
The oxidative homocoupling reaction of Grignard reagents in the presence of atmospheric oxygen molecules proceeded in the presence of a heptafluorotolyl-substituted perfluorocyclopentadienyl radical. The turnover number (TON) was over 30 for the coupling reactions of PhMgBr to give biphenyl. The organocatalyst could couple thienylmagnesium compounds to give bithiophene derivatives in up to 94% yield. Furthermore, a gram-scale synthesis of 6,6'-dimethoxybiphenyl-2,2'-diyl-bis(phosphonic acid diethyl ester) was demonstrated. Stabilization of the phenyl radical for the inhibition of the side reaction was also considered using DFT calculations.
- Korenaga, Toshinobu,Nitatori, Kaoru,Muraoka, Hiroki,Ogawa, Satoshi,Shimada, Kazuaki
-
p. 4835 - 4839
(2018/04/26)
-
- Water-soluble superbulky (η6- p -cymene) ruthenium(ii) amine: An active catalyst in the oxidative homocoupling of arylboronic acids and the hydration of organonitriles
-
A phosphine free water-soluble superbulky amine-ruthenium-arene complex (2) encompassing 2,6-bis(diphenylmethyl)-4-methylaniline was synthesised in good yield. 2 was characterized by FT-IR, 1H NMR, and 13C NMR spectroscopies, TGA and elemental analyses. The structure of 2 was confirmed by a single-crystal X-ray diffraction study. The ruthenium centre in 2 adopts the pseudo-octahedral geometry due to the η6-p-cymene ring and bulky aniline ligand along with two chloro groups. Besides, complex 2 was efficaciously employed as a catalyst in the hydration of organonitriles to amides. This reaction proceeds efficiently for a wide range of substrates in an environmentally benign medium and is an economically reasonable synthetic route to amides in good yields. In addition, 2 acts as an excellent catalyst in the oxidative homocoupling of arylboronic acids in water. A range of arylboronic acids undergo a homocoupling reaction in the presence of catalyst 2 to yield symmetrical biaryls in reasonable to good yields.
- Nirmala, Muthukumaran,Adinarayana, Mannem,Ramesh, Karupnaswamy,Maruthupandi, Mannarsamy,Vaddamanu, Moulali,Raju, Gembali,Prabusankar, Ganesan
-
supporting information
p. 15221 - 15230
(2018/09/29)
-
- Fast, Efficient and Low E-Factor One-Pot Palladium-Catalyzed Cross-Coupling of (Hetero)Arenes
-
The homocoupling of aryl halides and the heterocoupling of aryl halides with either aryl bromides or arenes bearing an ortho-lithiation directing group are presented. The use of a Pd catalyst, in combination with t-BuLi, allows for the rapid and efficient formation of a wide range of polyaromatic compounds in a one pot procedure bypassing the need for the separate preformation of an organometallic coupling partner. These polyaromatic structures are obtained in high yields, in 10 min at room temperature, with minimal waste generation (E-factors as low as 1.5) and without the need for strict inert conditions, making this process highly efficient and practical in comparison to classical methods. As illustration, several key intermediates of widely used BINOL-derived structures are readily prepared.
- Pinxterhuis, Erik B.,Visser, Paco,Esser, Iwan,Gualtierotti, Jean-Baptiste,Feringa, Ben L.
-
supporting information
p. 9452 - 9455
(2017/10/23)
-
- Au-Pd bimetallic nanoparticles supported on a high nitrogen-rich ordered mesoporous carbon as an efficient catalyst for room temperature Ullmann coupling of aryl chlorides in aqueous media
-
An ionic liquid derived highly nitrogen-rich mesoporous carbon supported Au-Pd alloy was found to be an efficient and recyclable catalyst for the Ullmann coupling reaction of various aryl chlorides at room temperature in aqueous media.
- Karimi, Babak,Barzegar, Hossein,Vali, Hojatollah
-
p. 7155 - 7158
(2018/07/05)
-
- One-pot two-step stannylation/Stille homocoupling of aryl bromides and iodides under solvent-free conditions
-
A new highly efficient solvent-free method for aryl bromide (iodide) homocoupling comprising the use of Pd(OAc)2/PCy3 system in the presence of CsF is suitable for substrates bearing functional groups not tolerant to lithium-, magnesium-, zincorganic reagents and strong bases.
- Gribanov, Pavel S.,Golenko, Yulia D.,Topchiy, Maxim A.,Philippova, Anna N.,Kirilenko, Nikita Yu.,Krivoshchapov, Nikolai V.,Sterligov, Grigorii K.,Asachenko, Andrey F.,Bermeshev, Maxim V.,Nechaev, Mikhail S.
-
p. 323 - 325
(2018/05/30)
-
- Nickel-Catalyzed Electrochemical Reductive Homocouplings of Aryl and Heteroaryl Halides: A Useful Route to Symmetrical Biaryls
-
Due to their widespread presence in functional materials and pharmaceuticals, biaryls are of fundamental importance in organic chemistry. Methods for the synthesis of symmetrical biaryls generally involve both metallic reduction and transition-metal catalysis. In this work, we show that electroreduction can also constitute a very relevant way to achieve the nickel-catalyzed reductive synthesis of symmetrical biaryl compounds. Therefore, it is demonstrated that both aryl and heteroaryl halides undergo reductive coupling to furnish the corresponding symmetrical biaryls in fair to excellent yields. Reactions are performed under very mild conditions thus ensuring important functional group tolerance.
- Rahil, Rima,Sengmany, Stéphane,Le Gall, Erwan,Léonel, Eric
-
p. 146 - 154
(2017/09/28)
-
- Reductive Homocoupling of Organohalides Using Nickel(II) Chloride and Samarium Metal
-
A homocoupling method for organohalides and organosulfonates promoted by samarium metal and HMPA, and catalyzed by NiCl2 has been developed. Various organohalides (benzyl, aryl, heterocyclic, alkenyl and alkyl halides), α-haloacetophenones, and phenyl organosulfonates were tolerated, and the reaction afforded coupling products with high efficiency. Excellent chemoselectivity was exhibited between halides and other groups, such as ?COOH, ?NO2, halogen, heterocyclic ring, ester, and ketone groups. The stereoselectivity suggested that the reaction mechanism might involve an organosamarium species.
- Liu, Yongjun,Xiao, Shuhuan,Qi, Yan,Du, Feng
-
p. 673 - 678
(2017/03/22)
-
- Optoelectronic and thermal properties of highly fluorescence emissive 2,2′-distyryl-[3,3′]-bithiophenes
-
Five newly designed organic small molecules (DSBTs, 1–5) with 3,3′-bithienyl unit had been successfully synthesized with 3-bromothiophene as the starting material. In both UV–vis absorption and fluorescence emission investigation, compound 3 with nitro-substitution exhibited the largest bathochromic shift and narrowest optical bandgap among 1–5. Further photophysical studies showed that 3 had obvious solvatochromism and aggregation-induced emission (AIE) property. The electrochemical properties and thermal stabilities studies demonstrated that 3 had high electron affinity and good thermal stability, which in combination with favorable optical properties indicated the prospect of 3 as a promising material in optoelectronic devices. Finally, theoretical calculations on structures, frontier molecular orbitals, UV–vis spectra and electronic transitions gave a good acknowledge of the relationship between optoelectronic properties and molecular structures.
- Cheng, Fengkai,Yin, Yan,Zhang, Guozhen,Wang, Yuan,Deng, Wei,Wu, Fanhong
-
p. 222 - 228
(2017/02/05)
-
- Cobalt-Catalyzed Oxidative Homocoupling of Arylzinc Species
-
A novel procedure for the synthesis of functionalized symmetrical biaryl compounds is described. The reaction proceeds via the oxidative homocoupling of arylzinc species formed by cobalt catalysis in the presence of air or p-benzoquinone depending on the nature of the functional group.
- Bourne-Branchu, Yann,Moncomble, Aurélien,Corpet, Martin,Danoun, Gregory,Gosmini, Corinne
-
p. 3352 - 3356
(2016/09/12)
-
- Homocoupling reactions of terminal alkynes and arylboronic compounds catalyzed by in situ formed Al(OH)3-supported palladium nanoparticles
-
Palladium nanoparticles supported on newly generated Al(OH)3was found to be a highly efficient catalyst in oxidative homo-couplings of (Het)aryl alkynes, (Het)arylboronic acids and potassium (Het)aryltrifluoroborates, respectively. Moderate to excellent yields of symmetrical 1,3-diynes and biaryls were obtained under mild conditions.
- Li, Xing,Li, Dongjun,Bai, Yana,Zhang, Congxia,Chang, Honghong,Gao, Wenchao,Wei, Wenlong
-
supporting information
p. 6996 - 7002
(2016/10/14)
-
- Miyaura Borylation and One-Pot Two-Step Homocoupling of Aryl Chlorides and Bromides under Solvent-Free Conditions
-
Solvent-free protocols for Miyaura borylation and the one-pot, two-step homocoupling of aryl halides are reported for the first time. Bis(dibenzylideneacetone)palladium(0) [Pd(dba)2] is an optimal source of palladium for Miyaura borylation, while for one-pot two-step homocoupling palladium(II) acetate [Pd(OAc)2] gives highest yields. Aryl bromides are coupled most efficiently using the DPEphos ligand. Chlorides are coupled using XPhos. The developed protocols are robust, versatile and easily reproducible on a large scale.
- Dzhevakov, Pavel B.,Topchiy, Maxim A.,Zharkova, Daria A.,Morozov, Oleg S.,Asachenko, Andrey F.,Nechaev, Mikhail S.
-
p. 977 - 983
(2016/04/05)
-
- A 2, 1, 3-benzothiadiazole and b thiophene derivatives and its synthetic method
-
The invention discloses 2,1,3-benzothiadiazoledithiophene derivatives. The derivatives relate to 5,8-dialkylbisthiophene benzothiadiazole. A preparation method includes preparing in sequence 5,5'-dialkyl-3,3'-bithiophene, 2,7-dialkylbenzodithiophene-4,5-diketone, 2,7-dialkylbenzodithiophene-4,5-dione dioxime, 2,7-dialkyl-4,5-dihydrobenzodithiophene-2,5-diamine, adding dropwise SOCl2 into a mixture of the 2,7-dialkyl-4,5-dihydrobenzodithiophene-2,5-diamine, triethylamine and CH2Cl2, and reacting at room temperature to obtain the 5,8-dialkylbisthiophene benzothiadiazole. The derivatives have good plane regularity, heat stability and good environment adaptability. The derivatives are liable to be processed to membrane, and can be used as intermediates in synthesis for organic solar energy battery materials.
- -
-
Paragraph 0023; 0036; 0037
(2016/10/09)
-
- Aryl Ketones as Single-Electron-Transfer Photoredox Catalysts in the Nickel-Catalyzed Homocoupling of Aryl Halides
-
An intriguing photoredox system for the homocoupling of aryl halides is reported wherein thioxanthone catalyzes a single-electron transfer from an amine reductant to nickel.
- Masuda, Yusuke,Ishida, Naoki,Murakami, Masahiro
-
supporting information
p. 5822 - 5825
(2016/12/18)
-
- A 2, 1, 3-benzothiadiazole and b thiophene derivative bromide and its synthetic method
-
The invention discloses 2,1,3-benzothiadiazoledithiophene derived brominated compounds. The brominated compounds relate to 5,8-bis(5-bromo-4-alkylthiophene-2-yl) thieno[2',3':3,4,3',2':5,6]benzo[1,2-c][1,2,5]thiadiazole. A preparation method includes preparing in sequence 5,8-dibromobithiophenebenzothiadiazole and 5,8-bis(4-alkylthiophene-2-yl)thienophenebenzothiadiazole, and reacting with an NBS brominating agent to prepare the 5,8-bis(5-bromo-4-alkylthiophene-2-yl) thieno[2',3':3,4,3',2':5,6]benzo[1,2-c][1,2,5]thiadiazole by using bithiophenebenzothiadiazole as an initial compound. The brominated compounds have good heat stability, chemical stability and solubility, and are intermediates in synthesis of organic solar energy battery materials.
- -
-
Paragraph 0040
(2016/10/07)
-
- Nickel-catalyzed one-pot deoxygenation and reductive homocoupling of phenols via C-O activation using TCT reagent
-
A new method for C-O bond activation of phenolic compounds has been achieved using 2,4,6-trichloro-1,3,5-triazine to utilize in one-pot Ni-catalyzed deoxygenation and reductive homocoupling reactions. With this simple method, phenolic compounds were converted to their corresponding arenes or biaryl compounds under mild conditions. The introduced methodology has a broad scope and demonstrates good functional group compatibility.
- Iranpoor, Nasser,Panahi, Farhad
-
supporting information
p. 214 - 217
(2015/01/30)
-
- Ligand-, base-, co-catalyst-free copper fluorapatite (CuFAP) as a versatile, ecofriendly, heterogeneous and reusable catalyst for an efficient homocoupling of arylboronic acid at ambient reaction conditions
-
This paper describes the first report in which copper species containing copper fluorapatite (CuFAP) acts as a versatile, eco-friendly, recyclable, heterogeneous catalyst for an efficient synthesis of symmetric biaryls from the homo-coupling of arylboronic acids in methanol solvent at ambient reaction conditions. The developed protocol is ligand-, base-, and co-catalyst-free, sustainable, mild, inexpensive, and compatible with a wide range of aromatic/heterocyclic boronic acids and provides the corresponding products in excellent yields without purification. The catalyst was easily recovered from the reaction mixture and reused several times without loss of activity.
- Mulla, Shafeek A. R.,Chavan, Santosh S.,Pathan, Mohsinkhan Y.,Inamdar, Suleman M.,Shaikh, Taufeekaslam M. Y.
-
p. 24675 - 24680
(2015/03/30)
-
- Recyclable and reusable Pd(OAc)2/PPh3/PEG-2000 system for homocoupling reaction of arylboronic acids under air without base
-
A stable and efficient Pd(OAc)2/PPh3/PEG-2000 catalytic system for homocoupling of arylboronic acids has been developed. In the presence of Pd(OAc)2 and PPh3, the homocoupling reaction of arylboronic acids was carried out smoothly in PEG-2000 at 70°C under air without base to afford a variety of symmetric biaryls in good to excellent yields. The isolation of the products was readily performed by extractionwith diethyl ether, and the Pd(OAc)2/PPh3/PEG-2000 systemcould be easily recycled and reused six times without significant loss of catalytic activity.
- Xia, Jianhui,Cheng, Mingzhu,Chen, Qiurong,Cai, Mingzhong
-
p. 113 - 116
(2015/01/30)
-
- METHOD FOR PRODUCING AROMATIC COMPOUND
-
A method is provided for producing an aromatic compound, including a step of mixing a compound represented by formula (A) and a compound represented by formula (B): in the presence of at least one phosphine compound selected from the group consisting of a phosphine represented by formula (C) and a phosphonium salt represented by formula (F): a base, a palladium compound, and an aprotic organic solvent.
- -
-
Paragraph 0523
(2015/11/30)
-
- N-Heterocyclic Carbene-Pd Polymers as Reusable Precatalysts for Cyanation and Ullmann Homocoupling of Aryl Halides: The Role of Solvent in Product Distribution
-
A main-chain N-heterocyclic carbene (NHC) polymer with N-dodecyl-substituted groups was found to be a highly efficient precatalyst for cyanation of various aryl halides by using nontoxic cyanic source [K4Fe(CN)6] under relatively mild reaction conditions. Several aryl iodides, bromides, and activated chlorides were successfully converted to their corresponding benzonitrile derivatives without using additives (such as reducing agents or exogenous organic ligands) in good to excellent yields. Our investigations showed that changing the solvent from DMF to polyethylene glycol (PEG-200) resulted in dramatic decline of cyanation product formation to the benefit of the Ullmann homocoupling reaction. The catalyst could be reused four and five times with only slight loss of activity in cyanation and the Ullmann coupling, respectively.
- Karimi, Babak,Vafaeezadeh, Majid,Akhavan, Pari Fadavi
-
p. 2248 - 2254
(2015/11/24)
-
- Diphenylphosphorylated PEG (DPPPEG) as a new support for generation of nano-Pd(0) as catalyst for carbon-carbon bond formation via copper-free Sonogashira and homocoupling reactions of aryl halides in PEG
-
In this study, synthesis and application of diphenylphosphorylated PEG200 (DPPPEG200) are described. Herein, we report a very simple procedure for the preparation of DPPPEG200 as a stable solid through the reaction of PEG200 with ClPPh2. This compound was used as a very suitable ligand for the in situ generation of nano-Pd(0) particles through its reaction with PdCl2 as a pre-catalyst. Isolation of this catalyst is very simple through addition of diethyl ether to the reaction mixture and centrifugations. Full characterization of the nano-Pd(0)/DPPPEG200 was performed by XRD spectra, UV-Vis spectra, and also by TEM image. This nano-complex was used as an efficient catalyst for copper-free Sonogashira and homocoupling reactions of aryl halides. The sonogashira reaction of aryl halides was conducted at 80 °C in PEG. However, the homocoupling reaction was performed at 100 °C for aryl iodides and activated aryl bromides and at 130 °C for deactivated aryl bromides and aryl chlorides in PEG. The catalyst was recovered and recycled for four consecutive runs.
- Iranpoor, Nasser,Firouzabadi, Habib,Riazi, Asma
-
p. 155 - 165
(2015/07/20)
-
- Benzodithieno-imidazole based π-conjugated fluorescent polymer probe for selective sensing of Cu2+
-
π-Conjugated polymers appended with binding sites are of considerable interest as an evolving new class of heavy and toxic metal ion sensors through fluorescence quenching. In this study we describe the synthesis and characterization of a p-bromophenyl substituted benzodithieno-imidazole based soluble and rigid π-conjugated polymer with N and S donors exhibiting outstanding sensitivity towards Cu2+ by emission quenching through photoinduced electron transfer (PET). Detailed photophysical and ion sensing studies have been demonstrated to understand insight of the polymer-metal ion interaction which is responsible for selective fluorescence quenching. The corresponding polymer is also explored as a thin-film polymeric sensor towards Cu2+ as monitored by a photoluminescence study.
- Giri, Dipanjan,Patra, Sanjib K.
-
p. 79011 - 79021
(2015/10/05)
-
- The transition-metal-catalyst-free oxidative homocoupling of organomanganese reagents prepared by the insertion of magnesium into organic halides in the presence of MnCl2·2LiCl
-
Organomanganese reagents were prepared by the insertion of magnesium into aryl halides in the presence of MnCl2·2LiCl. These organomanganese reagents smoothly undergo 1,2-addition, acylation, and Pd-catalyzed cross-coupling with various electrophiles. Especially, the oxidative homocoupling of organomanganese reagents was completed in one pot without an additional transition-metal catalyst.
- Peng, Zhihua,Li, Na,Sun, Xinyang,Wang, Fang,Xu, Lanjian,Jiang, Cuiyu,Song, Linhua,Yan, Zi-Feng
-
p. 7800 - 7809
(2014/12/10)
-
- Enatioselective Chalcogeno-Baylis-Hillman reaction of arylaldehydes with MVK and acrylates catalyzed by chiral thiepin-TiCl4 complex
-
In a rational chiral molecular design of chalcogenides, optically active thiepin with C2-symmetric chirality was synthesized from commercially available thiophene. Then enatioselective Chalcogeno-Baylis-Hillman reactions of arylaldehydes with methyl vinyl ketone (MVK) and acrylates were investigated in the presence of thiepin-Lewis acid complex. Finally, up to 64% ee was achieved in the presence of 0.2 equiv. of (S)-thiepin at 20°C. Enatioselective Chalcogeno-Baylis-Hillman reactions between benzaldehydes and acrylates were investigated in the presence of chiral thiepin-Lewis acid complex. Finally, up to 64% ee was achieved in the presence of 0.2 equiv. of (S)-thiepin at 20°C. Copyright
- Yin, Yan,Sun, Guofeng,Zhang, Heng,Zhou, Hong,Wu, Fanhong
-
supporting information
p. 365 - 369
(2014/05/20)
-
- A catalyst with two-coordinate nickel: Theoretical and catalytic studies
-
The bisadduct (cAAC)2NiIICl2 [1; cAAC = cyclic (alkyl)(amino)carbene] was directly synthesized by treating cAAC with NiCl2. Compound 1 was reduced to (cAAC)2Ni (2) by using lithium diisopropylamide or KC8. Crystals of 2 were stable under an inert gas for several months and decomposed upon heating above 165°C. On the basis of the calculated natural bond orbital charge values of the nickel atom in 2, the oxidation state of nickel was determined to be between NiI and Ni (+0.34). Theoretical calculations suggested a closed-shell singlet electronic configuration of 2 with little biradical character. Ab initio multiconfigurational C(R)ASSCF/CASPT2 calculations predicted a closed-shell singlet electronic configuration (Ni), whereas excited spin states possessed NiI character with unpaired electrons on neighboring carbon atoms. The catalytic activity of complex 2 was investigated for the homocoupling of various unactivated aryl chlorides/fluorides. The biaryls were obtained in good yields at moderate temperature. Theoretical studies showed that an intermediate containing NiIII was more favored than one with NiIV. The synthesis of (cAAC)2NiIICl2 (1) and its conversion into (cAAC)2Ni (2) through reduction is reported [cAAC = cyclic (alkyl)(amino)carbene]. Efficient reductive homocoupling of unactivated aryl chlorides and fluorides is catalyzed by 2 through C-Cl and C-F bond activation. Detailed high-level theoretical investigations are performed to understand the electronic and catalytic cycle of 2. Copyright
- Mondal, Kartik Chandra,Samuel, Prinson P.,Li, Yan,Roesky, Herbert W.,Roy, Sudipta,Ackermann, Lutz,Sidhu, Navdeep S.,Sheldrick, George M.,Carl, Elena,Demeshko, Serhiy,De, Susmita,Parameswaran, Pattiyil,Ungur, Liviu,Chibotaru, Liviu F.,Andrada, Diego M.
-
p. 818 - 823
(2014/03/21)
-
- A catalyst with two-coordinate nickel: Theoretical and catalytic studies
-
The bisadduct (cAAC)2NiIICl2 [1; cAAC = cyclic (alkyl)(amino)carbene] was directly synthesized by treating cAAC with NiCl2. Compound 1 was reduced to (cAAC)2Ni0 (2) by using lithium diisopropylamide or KC8. Crystals of 2 were stable under an inert gas for several months and decomposed upon heating above 165 C. On the basis of the calculated natural bond orbital charge values of the nickel atom in 2, the oxidation state of nickel was determined to be between NiI and Ni0 (+0.34). Theoretical calculations suggested a closed-shell singlet electronic configuration of 2 with little biradical character. Ab initio multiconfigurational C(R)ASSCF/CASPT2 calculations predicted a closed-shell singlet electronic configuration (Ni0), whereas excited spin states possessed NiI character with unpaired electrons on neighboring carbon atoms. The catalytic activity of complex 2 was investigated for the homocoupling of various unactivated aryl chlorides/fluorides. The biaryls were obtained in good yields at moderate temperature. Theoretical studies showed that an intermediate containing NiIII was more favored than one with NiIV. The synthesis of (cAAC)2NiIICl2 (1) and its conversion into (cAAC)2Ni (2) through reduction is reported [cAAC = cyclic (alkyl)(amino)carbene]. Efficient reductive homocoupling of unactivated aryl chlorides and fluorides is catalyzed by 2 through C-Cl and C-F bond activation. Detailed high-level theoretical investigations are performed to understand the electronic and catalytic cycle of 2.
- Mondal, Kartik Chandra,Samuel, Prinson P.,Li, Yan,Roesky, Herbert W.,Roy, Sudipta,Ackermann, Lutz,Sidhu, Navdeep S.,Sheldrick, George M.,Carl, Elena,Demeshko, Serhiy,De, Susmita,Parameswaran, Pattiyil,Ungur, Liviu,Chibotaru, Liviu F.,Andrada, Diego M.
-
supporting information
p. 818 - 823
(2015/04/27)
-
- Selectivity of Br/Li exchange and deprotonation of 4,4′-dibromo-3, 3′-bithiophene for synthesis of symmetrical and unsymmetrical dithienoheteroaromatic rings
-
The novel selective synthesis of symmetrical and unsymmetrical dithienoheteroaromatic rings (DTHAs) has been developed via intramolecular cyclization of 4,4′-dibromo-3,3′-bithiophene (3). Four reaction conditions including n-BuLi/Et2O, n-BuLi/T
- Han, Hui,Zhao, Wenling,Song, Jinsheng,Li, Chunli,Wang, Hua
-
supporting information
p. 2726 - 2730
(2013/04/23)
-
- Fe3O4 nanoparticle-supported Cu(ii)-β- cyclodextrin complex as a magnetically recoverable and reusable catalyst for the synthesis of symmetrical biaryls and 1,2,3-triazoles from aryl boronic acids
-
We report here on the preparation of an efficient, easily recoverable and reusable Fe3O4 magnetic nanoparticle-supported Cu(ii)-β-cyclodextrin complex catalyst for the synthesis of symmetrical biaryls and 1,2,3-triazoles from arylboronic acids. The presented Fe 3O4 magnetic nanoparticle-supported Cu(ii)-β- cyclodextrin complex catalyst was characterized by TEM, XRD, VSM, TGA, and FT-IR spectrometer. By using the catalyst, we have developed an efficient protocol for the homocoupling of aryl boronic acids for the synthesis of biaryls. The catalyst is also active in the synthesis of 1,2,3-triazoles via a one-pot reaction of an arylboronic acid with sodium azide in water followed by a click cyclization reaction with an alkyne at room temperature in air without any additives. The reusability of the prepared nanocatalyst was successfully examined four times with only a very slight loss of catalytic activity.
- Kaboudin, Babak,Mostafalu, Ramin,Yokomatsu, Tsutomu
-
p. 2266 - 2274
(2013/09/24)
-
- Water mediated Heck and Ullmann couplings by supported palladium nanoparticles: Importance of surface polarity of the carbon spheres
-
Heterogeneous palladium nanoparticle catalysts that are supported on amphiphilic carbon spheres (Pd@CSP) have been utilized for water-mediated Heck coupling reactions of aryl halides with different alkenes under phosphine free as well as aerobic conditions. Furthermore, a variety of Heck coupling reactions using different bases and solvents, including organic polar and non-polar solvents, have been explored. Aryl bromides are also well activated in Heck coupling reactions in organic polar solvent and as well as in water. In addition, Ullmann coupling reactions of aryl iodides have been catalyzed in water with the aid of phase transfer catalysts (PTC) in moderate yields. A plausible mechanism for the catalytic activity of Pd@CSP in the case of the Ullmann reaction is also established. It has been demonstrated that the hydrophobic effects of the catalyst surface play an important role in catalyst activity in water. In addition, the E-factor analysis verified that our present protocol is significantly comparable with other catalytic systems and explains the improved greenness. Moreover, the catalyst described in this process is not only greener, but also retains its significant activity for up to four catalytic cycles for the Heck coupling reactions. The surface polarity of the amphiphilic carbon spheres results in higher activity under these conditions.
- Kamal, Ahmed,Srinivasulu, Vunnam,Seshadri,Markandeya, Nagula,Alarifi,Shankaraiah, Nagula
-
p. 2513 - 2522
(2013/02/21)
-
- Ferrous salt-promoted homocoupling of arenediazonium tetrafluoroborates under mild conditions
-
A simple and efficient protocol has been developed for the synthesis of various symmetrical biaryls in good to excellent yields from the homocoupling reactions of arenediazonium salts with ferrous salt in carbon tetrachloride solution under mild reaction conditions. Moreover, the novel homocoupling has been demonstrated to proceed via an electron transfer reaction mechanism.
- Ding, Yiyuan,Song, Qingbao,Cheng, Kai,Qi, Chenze
-
p. 6269 - 6272,4
(2012/12/11)
-
- Pd-catalyzed oxidative homocoupling of arylboronic acids in aqueous ethanol at room temperature
-
The authors demonstrate for the first time that the Pd(OAc) 2/N,O-ligands act as catalysts toward homocoupling of arylboronic acid in aqueous ethanol (95%) under mild conditions: at room temperature and under aerobic condition. Under the optimal reaction conditions, all reactions gave the homocoupling products in good to excellent yields.
- Zhou, Zhonggao,Hu, Qiaosheng,Du, Ziyi,Xue, Jun,Zhang, Shiyong,Xie, Yongrong
-
p. 940 - 943
(2012/11/13)
-
- Carboxylate-based, room-temperature ionic liquids as efficient media for palladium-catalyzed homocoupling and sonogashira-hagihara reactions of aryl halides
-
Carboxylate-based salts are introduced as easily prepared, cheap and stable ionic liquids (ILs) that act as the base, ligand, reducing agent and media for the efficient phosphane-free, palladium-catalyzed homocoupling reaction of aryl iodides and bromides. The efficient copper and phosphane-free Sonagashira coupling reaction of aryl iodides and bromides is also demonstrated in these ILs. One of the ILs was also phosphorylated and showed high efficiency and recyclability as a medium, and was also used as a ligand for palladium-catalyzed homocoupling and copper-free Sonogashira reactions of aryl iodides and bromides. Copyright
- Iranpoor, Nasser,Firouzabadi, Habib,Ahmadi, Yasaman
-
experimental part
p. 305 - 311
(2012/02/03)
-
- Novel dithieno-benzo-imidazole-based Pb2+ sensors: Substituent effects on sensitivity and reversibility
-
Two novel dithieno-benzo-imidazole-based compounds (M2 and A2) showed remarkable sensitivities towards Pb2+ by 12-fold enhancement and 10-fold decay of fluorescence, respectively, in aqueous solutions. Substituent effects of different dithieno-benzo-imidazole-based moieties (M1, M2, A1 and A2) on the quantum yields, fluorescence lifetimes and sensitivities to Pb 2+ along with the reversibilities by S2- were investigated.
- Satapathy, Rudrakanta,Wu, Yen-Hsing,Lin, Hong-Cheu
-
supporting information; experimental part
p. 5668 - 5670
(2012/07/03)
-
- Novel thieno-imidazole based probe for colorimetric detection of Hg 2+ and fluorescence turn-on response of Zn2+
-
Novel thieno-imidazole based polymer P showed both colorimetric and ratiometric detections of Hg2+ as well as fluorometric detection of Zn2+ via fluorescence turn-on response with augmented lifetime. Its model polymer M did not show any such sensing capability under similar conditions, which further confirmed the unique sensitivity of P toward Hg 2+ and Zn2+ via the chelation of metal ions to both "S" and "N" heteroatoms.
- Satapathy, Rudrakanta,Wu, Yen-Hsing,Lin, Hong-Cheu
-
supporting information; experimental part
p. 2564 - 2567
(2012/07/14)
-
- Synthesis and characterization of reversible chemosensory polymers: Modulation of sensitivity through the attachment of novel imidazole pendants
-
Three novel electron donor-acceptor conjugated polymers (P1-P3) bearing various imidazole pendants have been synthesized. Their excellent photophysical and electrochemical properties make them suitable transduction materials for chemosensing applications. Indeed, polymers P1-P3 have been found to show remarkable sensing capabilities towards H+ and Fe2+ in semi-aqueous solutions. Upon titration with H+, polymers P1 and P2 showed hypsochromic shifts of their absorptions and photoluminescence (PL) maxima with enhanced fluorescence intensities. However, P3 showed diminished absorption and fluorescence intensities under similar conditions due to static quenching. The anomalous behavior of P3 compared with P1 and P2 has been clarified in terms of electronic distributions through computational analysis. Furthermore, P3 (KSV=1.03×107) showed a superior sensing ability towards Fe2+ compared with P1 (KSV=2. 01×106) and P2 (KSV=4.12×106) due to its improved molecular wire effect. Correspondingly, the fluorescence lifetime of P3 was greatly decreased (almost 11-fold) compared to those of polymers P1 (4.6-fold) and P2 (6.2-fold) in the presence of Fe2+. By means of a fluorescence on-off-on approach, chemosensing reversibilities in protonation-deprotonation and metallation-demetallation have been achieved by employing triethylamine (TEA) and the disodium salt of ethylenediaminetetraacetic acid (Na2-EDTA)/phenanthroline, respectively, as suitable counter ligands. 1H NMR titrations have revealed the unique behavior of P3 compared with P1 and P2. To the best of our knowledge, there have been no previous reports of Fe2+ sensors based on single imidazole receptors conjugated to a main-chain polymer showing such a diverse sensitivity pattern depending on their attached substituents.
- Satapathy, Rudrakanta,Padhy, Harihara,Wu, Yen-Hsing,Lin, Hong-Cheu
-
supporting information
p. 16061 - 16072
(2013/02/23)
-
- Environmentally friendly homocoupling reaction of functionalized potassium aryl trifluoroborates salts in aqueous media
-
The homocoupling reaction between potassium aryl trifluoroborates containing different functionalities promoted by a catalytic amount of Pd(OAc)2 is described. The methodology uses water as a solvent under aerobic conditions to give the corresponding biaryl compounds in good yields.
- Santos-Filho, Everaldo F.,Sousa, Jokderléa C.,Bezerra, Natércia M.M.,Menezes, Paulo H.,Oliveira, Roberta A.
-
supporting information; experimental part
p. 5288 - 5291
(2011/10/30)
-
- Suzuki-Miyaura reactions of the soluble guanylate cyclase inhibitor NS2028: A non-product specific route to C-8 substituted analogues
-
Both soluble guanylate cyclase (sGC) inhibitors ODQ 1 and NS2028 2 are synthesized via improved protocols. In the former case treating 3,4-dihydroquinoxalin-2(1H)-one oxime 8, which can be prepared in two steps from 1,2-benzenediamine, with 1,1′-carbonyldiimidazole (CDI) gives the dihydro-ODQ 10 that in the presence of KMnO4 oxidises to give ODQ 1 in an overall yield of 46% starting from 1,2-benzenediamine. In the latter case, the synthesis affords NS2028 2 from 2-amino-4-bromophenol 3 in three steps with an overall yield of 85% and avoids the need for chromatography. Furthermore, Suzuki-Miyaura reaction conditions are described that enable the preparation of 8-aryl and 8-heteroaryl derivatives of NS2028 directly from NS2028 2. Finally, demethylation of the 8-(methoxyphenyl) substituted analogues afforded the 8-(hydroxyphenyl) derivatives 40-42. All new products are fully characterised.
- Berezin, Andrey A.,Koutentis, Panayiotis A.
-
experimental part
p. 4069 - 4078
(2011/06/24)
-
- CuII-β-cyclodextrin complex as a nanocatalyst for the homo-and cross-coupling of arylboronic acids under ligand-and base-free conditions in air: Chemoselective cross-coupling of arylboronic acids in water
-
We report here the transition-metal-catalyzed chemoselective cross-coupling of arylbroronic acids in high yields without using ligand or base. We have developed an efficient copper-catalyzed protocol for the homocoupling and cross-coupling of arylboronic acids. The protocol is also suitable for the cross-coupling of aliphatic primary amines with arylboronic acids. Aminophenols and primary amines bearing an alcoholic substituent on the aliphatic chain were coupled with arylboronic acids, and the products were obtained with high C-N coupling selectivity. An effective catalyst was Cu2-β- cyclodextrin, which is readily available and structurally simple, but has not previously been explored as a catalyst.
- Kaboudin, Babak,Abedi, Yaghoub,Yokomatsu, Tsutomu
-
experimental part
p. 6656 - 6662
(2012/01/06)
-
- CuSO4-mediated homocoupling of arylboronic acids under ligand- and base-free conditions in air
-
The homocoupling of arylboronic acids mediated by very inexpensive and air stable copper(II) sulfate in N,N-dimethylformamide affords the corresponding symmetrical biaryls in moderate to good yields. The homocoupling reaction proceeds in air at 50 C in the presence of molecular sieves without any additives such as base and ligand. Georg Thieme Verlag Stuttgart · New York.
- Kaboudin, Babak,Haruki, Terumitsu,Yokomatsu, Tsutomu
-
experimental part
p. 91 - 96
(2011/02/28)
-
- Carbon-carbon bond formation via homocoupling reaction of substrates with a broad diversity in water using Pd(OAc)2 and agarose hydrogel as a bioorganic ligand, support and reductant
-
In this study, we have presented a new catalytic system in which Pd(OAc)2 has been used as a pre-catalyst and agarose as a degradable bioorganic ligand, support and reductant for carbon-carbon bond formation via homocoupling reaction of different aryl halides, β-bromo styrene, phenylboronic acid and phenylacetylene as the substrates. The reactions proceeded smoothly with high yields at temperature 100 °C in water without using any organic co-solvent, phosphorus ligand or reducing agents. The catalyst is recyclable and has been recycled for four times with a tiny amount of leaching of Pd into the reaction media. The amount of leaching has been determined by ICP analysis.
- Firouzabadi, Habib,Iranpoor, Nasser,Kazemi, Faezeh
-
scheme or table
p. 94 - 99
(2011/11/07)
-
- Catalytic homocoupling of aryl, alkenyl, and alkynyl halides with Ni(II)-complexes and zirconocene dichloride
-
A new catalytic system (cat. (H)2Phen(Me)2· NiCl2 or (MeO)2Dipyr(H)2·NiCl 2, cat. Zr(cp)2Cl2, 2 equiv Mn, and 2 equiv LiCl) has been developed to facilitate the homocoupling of a wide range of aryl, alkenyl, and alkynyl halides.
- Peng, Jianbiao,Liu, Xiang,Kishi, Yoshito
-
experimental part
p. 2172 - 2175
(2011/05/05)
-