- Preparation method of water-soluble vitamin E participated conjugated diyne compound
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The water-soluble vitamin E participates in the green preparation method of the conjugated diyne compound, the water serves as a reaction solvent, the use amount of the organic solvent is reduced, and zero emission of the solvent is realized. The excellent physicochemical properties of water are fully utilized, the reaction conditions are mild and efficient, the surfactant TPGS - 750 - M can be recycled through treatment, and the principle of environmental friendliness is completely met. The reaction substrate is wide in applicability, can catalyze the aryl alkyne, can catalyze the aliphatic hydrocarbon, and provides a simple and environment-friendly preparation method for the synthesis of the conjugated diyne. The copper catalyst which is more suitable for the reaction and reaction medium of the invention is screened out, and the yield is greatly improved.
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Paragraph 0112-0116
(2021/11/14)
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- Supporting a Cu@In2O3core-shell structure on N-doped graphitic carbon cuboctahedral cages for efficient photocatalytic homo-coupling of terminal alkynes
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Improving the separation efficiency of photogenerated carriers and exposing more active sites are two important factors to improve the photocatalytic efficiency of photocatalysts. Designing appropriate materials with special structure and composition to a
- Han, Xiguang,Li, Qiuyan,Wang, Xiaojun,Wang, Ya-Qun,Yang, Feng-Lei,Yuan, Yaya,Zhuang, Guilin
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supporting information
p. 24909 - 24914
(2021/11/27)
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- Rh(III)-Catalyzed [3 + 2] Spirocyclization of 2 H-Imidazoles with 1,3-Diynes for the Synthesis of Spiro-[imidazole-indene] Derivatives
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An effective strategy to synthesize spirocyclic compounds, [imidazole-4,1′-indene], has been efficaciously developed relied on Rh(III)-catalyzed [3 + 2] spirocyclization of 2H-imidazoles and 1,3-diynes with excellent chemselectivity and regioselectivity.
- Luo, Yi,Liu, Hao,Zhang, Jing,Liu, Man,Dong, Lin
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supporting information
p. 7604 - 7608
(2020/10/09)
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- Phosphorus(III)-Mediated, Tandem Deoxygenative Geminal Chlorofluorination of 1,2-Diketones
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Tetrasubstituted carbon containing two different halogen substituents was constructed in a single-step operation by utilizing the carbene-like reactivity of dioxaphospholene through the tandem reaction of electrophilic and nucleophilic halogenating reagents. It was crucial to devise non-dealkylatable phosphoramidite, which enabled the efficient formation of geminal chlorofluorides from various 1,2-diketones with (PhSO2)2NF and n-Bu4NCl. In addition, selective functionalization of the chlorine substituent was demonstrated, and the absence of halogen scrambling was confirmed.
- Choi, Garam,Chung, Won-Jin,Hwang, Sunjoo,Jang, Hanna,Kim, Ha Eun
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supporting information
p. 4190 - 4195
(2020/06/27)
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- Stereoselective Synthesis of Highly Substituted Conjugated Dienes via Pd-Catalyzed Carbonylation of 1,3-Diynes
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The stereoselective synthesis of conjugated dienes was realized for the first time via Pd-catalyzed alkoxycarbonylation of easily available 1,3-diynes. Key to success is the utilization of the specific ligand 1,1′-ferrocenediyl-bis(tert-butyl(pyridin-2-yl)phosphine) (L1), which allows this novel transformation to proceed at room temperature. A range of 1,2,3,4-tetrasubstituted conjugated dienes are obtained in this straightforward access in high yields and selectivities. The synthetic utility of the protocol is showcased in the concise synthesis of several important intermediates for construction of natural products rac-cagayanin, rac-galbulin, rac-agastinol, and cannabisin G.
- Liu, Jiawang,Yang, Ji,Baumann, Wolfgang,Jackstell, Ralf,Beller, Matthias
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supporting information
p. 10683 - 10687
(2019/07/04)
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- Metallomicelle catalyzed aerobic tandem desilylation/Glaser reaction in water
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PEG-grafted nitrogen ligands were synthesized. The corresponding copper complexes serve as metallomicellar nanoreactors for the aerobic tandem desilylation/Glaser coupling of TMS-protected alkynes in water. The protocol is also suitable for base-free homocoupling of terminal alkynes. The metallomicellar catalyst could be recycled 5 times with minor loss of reactivity.
- Tang, Shanyu,Li, Longjia,Ren, Xuanhe,Li, Jiao,Yang, Guanyu,Li, Heng,Yuan, Bingxin
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supporting information
p. 2899 - 2904
(2019/06/17)
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- Unraveling the Mechanism of 1,3-Diyne Cross-Metathesis Catalyzed by Silanolate-Supported Tungsten Alkylidyne Complexes
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The benzylidyne complex [PhC≡W{OSi(OtBu)3}3] (1) catalyzed the cross-metathesis between 1,4-bis(trimethylsilyl)-1,3-butadiyne (2) and symmetrical 1,3-diynes (3) efficiently, which gave access to TMS-capped 1,3-diynes RC≡C?C≡CSiMesub
- Schnabel, Tobias M.,Melcher, Daniel,Brandhorst, Kai,Bockfeld, Dirk,Tamm, Matthias
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supporting information
p. 9022 - 9032
(2018/06/29)
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- Polymer-Supported Cu–Nanoparticle as an Efficient and Recyclable Catalyst for Oxidative Homocoupling of Terminal Alkynes
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Abstract: Copper nanoparticle on polyaniline support was synthesised by using in situ polymerisation and composite formation technique. This metal polymer nanocomposites material is found to be efficient for homocoupling of terminal alkynes which afford s
- Aziz, Sk Tarik,Islam, Rafique Ul
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p. 205 - 213
(2017/11/16)
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- Continuous-flow oxidative homocouplings without auxiliary substances: Exploiting a solid base catalyst
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The catalytic oxidative dimerization of aromatic amines and acetylenes is of outstanding synthetic importance among homocoupling reactions. Both transformations necessitate the use of extraneous bases and ligands, which contains significant disadvantages as concerns environmental impacts and process costs. We exploited the inherent basic character of a copper-containing layered double hydroxide to facilitate the catalytic homocouplings of alkynes and aniline derivatives without the need for any auxiliary substances. The reactions were studied in a continuous-flow system to achieve extended parameter spaces for chemical intensification, and also to avoid undesired reaction pathways by means of strategic control over the residence time. Valuable 1,4-disubstituted 1,3-diynes and diversely substituted aromatic azo compounds were achieved chemoselectively in excellent yields and in short process times even on preparative scales.
- ?tv?s, Sándor B.,Georgiádes, ádám,Mészáros, Rebeka,Kis, Koppány,Pálinkó, István,Fül?p, Ferenc
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- Cobalt Catalyzed, Regioselective C(sp2)-H Activation of Amides with 1,3-Diynes
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The development of a first row transition metal (cobalt)-based catalyst for the as yet unexplored C-H activation-driven reaction of 1,3-diynes, themselves a functional class of interest in a range of application areas, to form isoquinolinones - an importa
- Kathiravan, Subban,Nicholls, Ian A.
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supporting information
p. 4758 - 4761
(2017/09/23)
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- Nitro resin supported copper nanoparticles: An effective heterogeneous catalyst for [Formula presented] cross coupling and oxidative [Formula presented] homocoupling
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In the present study, we investigate the synthesis and catalytic activity of copper nanoparticles (CuNPs) stabilized onto a novel nitro functionalized polystyrene resin. The deposited nanoparticles were characterized by various analytical techniques and TEM images, revealed uniformly distributed copper nanoparticles of sizes 3–9?nm. We effectively used the resin impregnated CuNPs for [Formula presented] coupling of various aromatic amines with aryl halides and for the oxidative [Formula presented] homocoupling of phenyacetylene. Further, recycling of the catalyst, leaching of metal ions and post reaction changes in the support were studied and it was concluded that the support acts as oxidant during the homocoupling of phenyl acetylene which is oxidative by nature.
- Barot, Nirav,Patel, Sunil B.,Kaur, Harjinder
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- Transition metal-free dimerization of alkynes using hypervalent iodine reagents
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This communication describes the use of hypervalent iodine reagents to facilitate the homo-coupling of terminal alkynes. A variety of different aliphatic and aromatic alkynes were successfully dimerized when using acetoxy-benziodoxole as the activating agent under operationally simple transition metal-free conditions.
- Sch?rgenhumer, Johannes,Waser, Mario
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supporting information
p. 1678 - 1680
(2016/04/04)
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- Ionic liquid-promoted Copper(II)-Catalyzed homocoupling of terminal alkynes in aqueous phase or under solvent-limited conditions
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A reusable ionic liquid 1-butyl-3-methylimidazolium bromide/Cu(II) system was proven to be a reusable catalyst for the homocoupling of terminal alkynes at mild temperature using air as oxidant in aqueous phase or under solvent-limited conditions. In most cases, good to excellent yields can be achieved, either aromatic alkynes or aliphatic alkynes were used as substrates. The homocoupling products 1,3-diynes were separated by extraction from the reaction system. And the activity of residue showed it could be reused for 3 and 6 cycles respectively under the aqueous phase conditions and solventlimited conditions. Furthermore, this reaction can be easily scaled up to gram level.
- Li, Shiguang,Chen, Xi,Chen, Jinping,Gong, Hang
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supporting information
p. 794 - 797
(2016/08/02)
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- 3-(Diphenylphosphino)propanoic acid: An efficient ligand for the Pd/Cu-catalyzed homo-coupling of terminal alkynes in the presence of oxygen at room temperature
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A simple, yet efficient system for PdCl2/CuI to catalyze the homo-coupling reactions of various terminal alkynes has been developed using 3-(diphenylphosphino)propanoic acid as ligand in the presence of oxygen. The alkynes, including aromatic, heteroaromatic and aliphatic alkynes, were transformed at room temperature into the corresponding 1,3-diynes in moderate to excellent yields. The turnover number was up to 1.04×103.
- Liu, Yashuai,Gu, Ningning,Liu, Ping,Xie, Jianwei,Ma, Xiaowei,Liu, Yan,Dai, Bin
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p. 736 - 738
(2015/11/09)
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- Oxidative homocoupling of terminal alkynes under palladium-, ligand- and base-free conditions using Cu(II)-clay as a heterogeneous catalyst
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Homocoupling of terminal alkynes to 1,3-diynes has been investigated with Cu(II)-modified clay under mild and operationally simple conditions without the use of any ligand or a stabilizing agent. The catalyst is robust, ecofriendly, efficient, furnishes g
- Dar, Bashir Ahmad,Vyas, Dushyant,Shrivastava, Varsha,Farooq, Saleem,Sharma, Amit,Sharma, Sadhana,Sharma, Parduman R.,Sharma, Meena,Singh, Baldev
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p. 316 - 323
(2014/04/17)
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- Copper-catalyzed homo- and cross-coupling reactions of terminal alkynes in ethyl lactate
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The bio-based chemical ethyl lactate (EL) has been discovered to be an excellent medium for the Glaser-type homo- and cross-coupling reactions of terminal alkynes. Good to excellent yields of conjugate diynes have been obtained under ligand-free and mild
- Wan, Jie-Ping,Cao, Shuo,Jing, Yanfeng
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p. 631 - 634
(2014/08/05)
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- A mild CuI-catalyzed Glaser-type homo-coupling reaction using α,α-dibromo-β-dicarbonyl compounds as oxidants
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Exploration of α,α-dibromo-β-dicarbonyl compounds as novel organic oxidants for the mild Cu(I)-catalyzed Glaser-type homo-coupling reaction has been achieved, which provides an alternatively efficient pathway for the construction of 1,3-conjugated structures. In addition, the mechanism of this reaction was investigated.
- Fan, Xiaohui,Li, Na,Shen, Tong,Cui, Xiao-Meng,Lv, Hao,Zhu, Hong-Bo,Guan, Yong-Hong
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supporting information
p. 256 - 261
(2014/01/06)
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- Enaminone ligand-assisted homo- and cross-coupling of terminal alkynes under mild conditions
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Copper-catalyzed oxidative coupling reactions of terminal alkynes have been performed at room temperature by using enaminone as effective ligand. Both symmetrical and unsymmetrical 1,3-diynes bearing various functional groups have been synthesized in mode
- Liu, Yunyun,Wang, Chunping,Wang, Xiaobo,Wan, Jie-Ping
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p. 3953 - 3955
(2013/07/25)
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- Ligand-free synthesis of 1,4-disubstituted-1,3-diynes by iron/copper cocatalyzed homocoupling of terminal alkynes
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A simple and efficient protocol for Fe/Cu cocatalyzed oxidative homocoupling reaction of terminal alkynes to symmetrical 1,4-disubstituted-1,3- diynes was presented. The results showed that both CuBr and FeCl3 played crucial roles in the reaction. It is noteworthy that this protocol employs mild, efficient, aerobic and ligand free conditions. The alkynes, including aromatic, heteroaromatic and aliphatic alkynes, were transformed into the corresponding 1,3-diynes in good to excellent yields. A simple and efficient protocol for Fe/Cu cocatalyzed oxidative homocoupling reaction of terminal alkynes to symmetrical 1,4-disubstituted-1,3-diynes was presented. The results showed that both CuBr and FeCl3 played crucial roles in the reaction. It is noteworthy that this protocol employs mild, efficient, aerobic and ligand free conditions. The alkynes, including aromatic, heteroaromatic and aliphatic alkynes, were transformed into the corresponding 1,3-diynes in good to excellent yields. Copyright
- Wang, Peipei,Liu, Xiaoyan,Zhang, Songlin
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p. 187 - 194
(2013/08/24)
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- Sonogashira cross-coupling reaction in 4-chloro-2- trichloromethylquinazoline series is possible despite a side dimerization reaction
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We studied the Sonogashira coupling reaction between 4-chloro-2- trichloromethylquinazoline and various terminal alkynes, mainly in phenylacetylene series. A brief review of the literature shows that mono- or polybromo/chloromethylated substrates, especia
- Kieffer, Charline,Verhaeghe, Pierre,Primas, Nicolas,Castera-Ducros, Caroline,Gellis, Armand,Rosas, Roselyne,Rault, Sylvain,Rathelot, Pascal,Vanelle, Patrice
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p. 2987 - 2995
(2013/03/29)
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- Practical oxidative homo- and heterocoupling of terminal alkynes catalyzed by immobilized copper in MCM-41
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A practical oxidative homo- and heterocoupling of terminal alkynes was achieved in CH2Cl2 at 25 °C by using a 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized copper(I) complex (MCM-41-2N-CuI, 1 mol-%) as the catalyst, piperidine (0.1 or 3 equiv.) as the base, and air as the environmentally friendly co-oxidant, yielding a variety of symmetrical and unsymmetrical 1,4-disubstituted 1,3-diynes in good to excellent yields. This heterogeneous copper catalyst showed a higher catalytic activity than CuI and can be recovered and recycled by a simple filtration of the reaction mixture and used for at least 10 consecutive runs without any decrease in activity. A practical oxidative homo- and heterocoupling of terminal alkynes was achieved in CH2Cl2 at 25 °C by using a 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized copper(I) complex (MCM-41-2N-CuI, 1 mol-%) as the catalyst and air as the environmentally friendly oxidant, yielding a variety of symmetrical and unsymmetrical 1,4-disubstituted 1,3-diynes in good to excellent yields.
- Xiao, Ruian,Yao, Ruiya,Cai, Mingzhong
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experimental part
p. 4178 - 4184
(2012/09/22)
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- CuI-catalyzed homocoupling of terminal alkynes to 1,3-diynes
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A simple and efficient protocol for CuI-catalyzed oxidative homocoupling reaction of terminal alkynes to symmetrical 1,4-disubstituted 1,3-diynes was reported. The reaction can be carried out in the open air, using NaOAc as a base in the absence of any other additives. A variety of terminal alkynes were converted to the corresponding 1.3-diynes in good to excellent yields without any side product formation. Copyright
- Yin, Kun,Li, Chun-Ju,Li, Jian,Jia, Xue-Shun
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experimental part
p. 16 - 20
(2011/09/16)
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- CuCl-catalyzed green oxidative alkyne homocoupling without palladium, ligands and bases
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CuCl-catalyzed green oxidative homocoupling of terminal alkynes produces symmetrical 1,4-disubstituted 1,3-diynes in good to excellent yields, using air as an environmentally friendly oxidant and the occurrence of water as exclusive byproduct in the whole process, and eliminating the need for ligands, bases, oxidants and expensive palladium catalysts. The Royal Society of Chemistry.
- Yin, Kun,Li, Chunju,Li, Jian,Jia, Xueshun
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supporting information; experimental part
p. 591 - 593
(2011/05/04)
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- Copper-catalyzed oxidative alkyne homocoupling without palladium, ligands and bases
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Copper-catalyzed green oxidative homocoupling of terminal alkynes can be run to produce symmetrical 1,4-disubstituted 1,3-diynes in good to excellent yields, using air as environmentally friendly oxidant and the occurrence of water as exclusive byproduct in the whole process. This eliminates the need for ligands, bases, oxidants and expensive palladium catalysts.
- Jia, Xueshun,Yin, Kun,Li, Chunju,Li, Jian,Bian, Haishan
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experimental part
p. 2175 - 2178
(2011/09/16)
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- An efficient copper-catalyzed homocoupling of terminal alkynes to give symmetrical 1,4-disubstituted 1,3-diynes
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A facile and efficient pathway for the copper iodide and ligand N,N,N',N'-tetramethylethane-1,2-diamine promoted homocoupling reaction of terminal alkynes under ambient temperature and air as an oxidant was reported. The alkynes, including aromatic alkynes and aliphatic alkynes, could afford the symmetrical 1,4-disubstituted 1,3-diynes in good to excellent yields. Copyright
- Zhang, Songlin,Liu, Xiaoyan,Wang, Tongqiang
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supporting information; experimental part
p. 1463 - 1466
(2011/08/07)
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- An alternative approach to aldol reactions: Gold-catalyzed formation of boron enolates from alkynes
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A new method for enolate generation via the gold-catalyzed addition of boronic acids to alkynes is reported. The formation of boron enolates from readily accessible ortho-alkynylbenzeneboronic acids proceeds rapidly with 2 mol % PPh3AuNTf2
- Koerner, Cindy,Starkov, Pavel,Sheppard, Tom D.
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supporting information; experimental part
p. 5968 - 5969
(2010/07/05)
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- Synthesis of butadiynes
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Provided is a method for the synthesis of 1,4-dicyclopropyl-1,3-butadiyne from CPA. Such butadiyne is prepared by oxidative coupling of cyclopropyl acetylene (CPA) using catalytic amounts each of copper (I)chloride and tetrametylethylenediamine (TMEDA) in isopropanol under aerobic conditions. The resulting butadiyne can serve as a fuel or a fuel additive for combustion in engines propelling motor vehicles, marine vessels, aircraft, rockets and other vehicles.
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Page/Page column 2
(2008/06/13)
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- Die Reaktivitaet der 1,3-Butadiin-Einheiten in den "explodierenden" Rotanen - eine Krone aus Thiophenen
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Stichworte: Alkine * Kronenverbindungen * Makrocyclen * Rotane * Thiophene
- Kozhushkov, Sergei,Haumann, Thomas,Boese, Roland,Knieriem, Burkhardt,Scheib, Stefan,et al.
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p. 859 - 862
(2007/10/02)
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- Regioselective coupling of ethynylcyclopropane units: Hexaspiro[2.0.2.4.2.0.2.4.2.0.2.4]triaconta-7,9,17,19,27,29-hexayne
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Regioselective synthetic methods are reported for the head to head, head to tail, and tail to tail coupling of ethynylcyclopropanes. Oxidative cyclization of the head to head dimer 5-H2 under high dilution conditions gave the title compound, an 18-membered macrocycle comprising six acetylenic units and six spirocyclopropanes that alternate pairwise around the ring. An X-ray crystal structure and spectroscopic properties of this novel macrocycle are reported.
- De Meijere, Armin,Jaekel, Frank,Simon, Arndt,Borrmann, Horst,K?hler, Jürgen,Johnels, Dan,Scott, Lawrence T.
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p. 3935 - 3938
(2007/10/02)
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