- Flexible Construction of Functionalized-Pyrroles under Palladium or Copper Catalysis in the Presence of BF3 ? Et2O
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We have developed a flexible approach enabling the access to highly functionalized pyrroles under palladium or copper catalysis in the presence of BF3 ? Et2O. This catalytic methodology utilizes commercially available amines as react
- Guo, Wusheng,Liu, Teng,Liu, Yin,Wei, Kun,Yan, Biwei
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supporting information
(2022/01/26)
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- Organoborane-catalyzed selective 1,2-reduction of alkynones with hydride transfer: Synthesis of benzyl alkynes
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Benzyl alkynes are important organic building blocks in organic synthesis. We report herein a B(C6F5)3-catalyzed site-selective 1,2-reduction of readily available alkynones to access benzyl alkyne derivatives. Under the de
- Li, Huilin,Man, Qinghong,Ren, Yangqing,She, Xuegong,Wang, Lei,Yang, Mingyu,Yang, Zhigang,Zhai, Lele
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supporting information
(2022/01/28)
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- Atom-Economic Synthesis of Highly Functionalized Bridged Ring Systems Initiated by Ring Expansion of Indene-1,3-dione
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An atom economic procedure for the regioselective synthesis of bridged seven-membered-ring compounds from simple reactants such as ynones and indene-1,3-dione has been developed. This process was realized through the one-pot reactions of ring-expansion of
- Mu, Yuanyang,Yao, Qiyi,Yin, Liqiang,Fu, Siyi,Wang, Mengdan,Yuan, Yang,Kong, Lingkai,Li, Yanzhong
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p. 6755 - 6764
(2021/05/06)
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- Straightforward Stereoselective Synthesis of Seven-Membered Oxa-Bridged Rings through in Situ Generated Cycloheptenol Derivatives
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An iodine-mediated stereoselective synthesis of seven-membered oxa-bridged rings via in situ generated cycloheptenols was reported. This process was realized through the combination of C-C σ-bond cleavage and C-O bond-forming reactions in a one-pot fashion from simple and easily accessible raw materials. The formation of carbon radicals initiated by I2 was the key to the reaction.
- Wang, Mengdan,Yin, Liqiang,Cheng, Lu,Yang, Yajie,Li, Yanzhong
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p. 12956 - 12963
(2021/09/13)
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- Selective Insertion of Alkynes into C-C σ Bonds of Indolin-2-ones: Transition-Metal-Free Ring Expansion Reactions to Seven-Membered-Ring Benzolactams or Chromone Derivatives
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An unprecedented ring expansion reaction of indolin-2-ones with alkynyl ketones under transition-metal-free conditions has been developed. Base-promoted selective cleavage of a C-C σ bond of the amide is the key in this process, which provides a straightf
- Wang, Mengdan,Yang, Yajie,Song, Bo,Yin, Liqiang,Yan, Shuhui,Li, Yanzhong
-
supporting information
p. 155 - 159
(2020/01/03)
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- Gold-Catalyzed Regioselective Synthesis of Pyrazolo[1,4]oxazepines via Intramolecular 7-endo-dig Cyclization
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An efficient gold-catalyzed intramolecular regioselective synthesis of pyrazolo[1,4]oxazepines were developed from alkynyl-substituted pyrazoles via 7-endo dig cyclization. In this reaction a new C–N bond was formed and substituted pyrazolo[1,4]oxazepines
- Doddi, Venkata Ramana,Karunakar, Galla V.,Purnachandar, Dalovai,Raju, Chittala Emmaniel,Sreenivasulu, Gottam,Thummala, Yadagiri
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supporting information
(2020/06/30)
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- DBU-Catalyzed Rearrangement of Secondary Propargylic Alcohols: An Efficient and Cost-Effective Route to Chalcone Derivatives
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A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed rearrangement of diarylated secondary propargylic alcohols to give α,β-unsaturated carbonyl compounds has been developed. The typical 1,3-transposition of oxy functionality, characteristic of Mayer-Schuster rearrangements, is not observed in this case. A broad substrate scope, functional-group tolerance, operational simplicity, complete atom economy, and excellent yields are among the prominent features of the reaction. Additionally, the photophysical properties and crystal-structure-packing behavior of selected compounds were investigated and found to be of interest.
- De, Rimpa,Savarimuthu, Antony,Ballav, Tamal,Singh, Pijush,Nanda, Jayanta,Hasija, Avantika,Chopra, Deepak,Bera, Mrinal K.
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supporting information
p. 1587 - 1592
(2020/08/28)
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- Transition-metal-free C-C σ-bond activation of α-aryl ketones and subsequent Zn-catalyzed intramolecular cyclization: synthesis of tetrasubstituted furans
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A highly atom-economical protocol for the synthesis of tetrasubstituted furans has been developed. This process is realized through the tandem reactions of Cs2CO3 promoted C-C σ-bond activation of α-aryl ketones followed by Zn-cataly
- Yuan, Yang,Tan, Hailu,Kong, Lingkai,Zheng, Zhong,Xu, Murong,Huang, Jiaqi,Li, Yanzhong
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p. 2725 - 2733
(2019/03/12)
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- Phosphorous acid promoted isomerization of propargyl alcohols to α,β-unsaturated carbonyl compounds
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A metal-free and two-phase protocol for the Meyer-Schuster isomerization of propargyl alcohols to the corresponding α,β-unsaturated carbonyl compounds has been achieved in the presence of stoichiometric phosphorous acid aqueous solution, which produces the desired products in high yields with excellent stereoselectivity. Compared with the traditional methods, the procedure features broad scope of the substrates, mild conditions, and easy separation, providing an appealing alternative to the Meyer-Schuster reaction.
- Gan, Xiaotang,Fu, Zuqi,Liu,Yan, Yani,Chen, Chao,Zhou, Yongbo,Dong, Jianyu
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supporting information
(2019/07/12)
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- Cascade and Effective Syntheses of Functionalized Tellurophenes
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A one-pot and transition-metal-catalyst-free synthetic strategy to construct functionalized tellurophenes has been developed. Substituted 1,1-dibromo-1-en-3-ynes are smoothly converted to tellurophenes with telluride salts in high yield via a series of cascade reactions through reductive debromination, hydrotelluration, nucleophilic cyclization, and aromatization. Close inspection of the results clearly showed that the reactivity of in situ prepared telluride salts are significantly influenced by the polarity of the solvent system and the electronic nature of the substituent on the enyne substrate. This method reports the first direct synthesis of 3-aryltellurophenes in high yields at room temperature. This novel reaction strategy is also found to be a promising synthetic method for multisubstituted tellurophenes and selenophenes.
- Karapala, Vamsi Krishna,Shih, Hong-Pin,Han, Chien-Chung
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supporting information
p. 1550 - 1554
(2018/03/23)
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- Transition-Metal-Free Ring Expansion Reactions of Indene-1,3-dione: Synthesis of Functionalized Benzoannulated Seven-Membered Ring Compounds
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A novel ring expansion reaction of indene-1,3-dione with alkynyl ketones under transition-metal-free conditions has been developed. This process offers an efficient and direct way to synthesize benzoannulated seven-membered rings or fused-ring compounds t
- Yao, Qiyi,Kong, Lingkai,Wang, Mengdan,Yuan, Yang,Sun, Ruizhuo,Li, Yanzhong
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supporting information
p. 1744 - 1747
(2018/04/14)
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- Direct Substitution of Secondary and Tertiary Alcohols to Generate Sulfones under Catalyst- and Additive-Free Conditions
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An environmentally benign protocol that affords propargylic sulfones containing highly congested carbon centers from easily accessible alcohols and sulfinic acids with water as the only byproduct is reported. The reaction proceeded via an in situ dehydrative cross-coupling process by taking advantage of the synergetic actions of multiple hydrogen bonds rather than relying on an external catalyst and/or additives to achieve high product distribution.
- Liu, Yanan,Xie, Peizhong,Sun, Zuolian,Wo, Xiangyang,Gao, Cuiqing,Fu, Weishan,Loh, Teck-Peng
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supporting information
p. 5353 - 5356
(2018/09/13)
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- Gold-Catalyzed 1,4-Carbooxygenation of 3-En-1-ynamides with Allylic and Propargylic Alcohols via Non-Claisen Pathways
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Gold-catalyzed 1,4-carbooxygenations of 3-en-1-ynamides with allylic alcohols and propargylic alcohols yield α,β-unsaturated amides through non-Claisen pathways; the mechanisms involve ionization of the initial gold enol ethers to form C-bound gold dienolates that capture allylic or propargylic cations to yield the observed products. Our18O-labeling experiments exclude a direct gold-catalyzed allylation or propargylation on these 3-en-1-ynamides. (Figure presented.).
- Giri, Sovan Sundar,Lin, Li-Hsuan,Jadhav, Prakash Daulat,Liu, Rai-Shung
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supporting information
p. 590 - 596
(2017/02/23)
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- Base-mediated insertion reaction of alkynes into carbon-carbon σ-bonds of ethanones: synthesis of hydroxydienone and chromone derivatives
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Transition-metal free insertions of alkynes into carbon-carbon σ-bonds of ethanones have been reported. These tandem reactions offer an efficient synthesis of hydroxydienones and multi-substituted chromones. This is the first example of base-promoted insertion reactions of isolated carbon-carbon triple bonds into carbon-carbon σ-bonds with active methylene compounds bearing only one electron-withdrawing group.
- Zhang, Fangfang,Yao, Qiyi,Yuan, Yang,Xu, Murong,Kong, Lingkai,Li, Yanzhong
-
supporting information
p. 2497 - 2500
(2017/04/03)
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- Highly Efficient Synthesis of Multi-Substituted Allenes from Propargyl Acetates and Organoaluminum Reagents Mediated by Palladium
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A simple and mild catalytic S N 2′ substitution reaction of propargyl acetates with organoaluminum reagents is reported. The S N 2′ substitution reaction of propargyl acetates with organoaluminum reagents mediated by Pd(PhP 3) 2 Cl 2 (1 mol%)/PPh 3 (2 mol%)/K 2 CO 3 in tetrahydrofuran at 60 °C for 3-4 hours afforded the corresponding multi-substituted allenes in good yields (up to 94%) with high selectivities (up to 99%). The process was simple and easily performed, which offers an efficient method to synthesize the multi-substituted allene derivatives.
- Zhang, Zhen,Shao, Xuebei,Zhang, Gang,Li, Qinghan,Li, Xinying
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p. 3643 - 3653
(2017/08/16)
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- Base-Promoted Tandem Reaction towards Conjugated Dienone or Chromone Derivatives with a Cyano Group: Insertion of Alkynes into C–C σ-Bonds of 3-Oxopropanenitriles
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Base-promoted insertion reactions of alkynes into the C–C σ-bonds of α-cyano ketones were established to construct highly functionalized conjugated olefins or chromone derivatives via transition metal-free tandem reactions. These reactions are initialized through the nucleophilic attack of α-cyano ketones to alkynones followed by intramolecular nucleophilic addition/ring-opening to furnish the cyano-containing alkenes. In the cases of alkynones bearing an ortho-halide-substituted aryl ring, a further C–O bond coupling reaction occurs to afford chromone derivatives in good to high yields. Various alkynones bearing alkyl or aryl substituents were compatible in the reaction. This reaction has the potential to become a general synthetic protocol for the preparation of cyano-substituted olefins and chromones due to the abundance of easily accessible starting materials possessing diverse substituent groups. (Figure presented.).
- Yao, Qiyi,Kong, Lingkai,Zhang, Fangfang,Tao, Xianghua,Li, Yanzhong
-
supporting information
p. 3079 - 3084
(2017/09/13)
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- Synthesis of 2-Sulfenylindenones via One-Pot Tandem Meyer-Schuster Rearrangement and Radical Cyclization of Arylpropynols with Disulfides
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A tandem annulation of arylpropynols with disulfides has been developed for the synthesis of 2-sulfenylindenone derivatives. The reaction pathway involves one-pot tandem Meyer-Schuster rearrangement of arylpropynols and successive radical cyclization with disulfides. Various arylpropynols and disulfides with a number of functional groups are compatible in this reaction that affords the corresponding 2-sulfenylindenones in moderate to good yields.
- Zhang, Xing-Song,Jiao, Jun-Ying,Zhang, Xiao-Hong,Hu, Bo-Lun,Zhang, Xing-Guo
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p. 5710 - 5716
(2016/07/13)
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- Insertion of Isolated Alkynes into Carbon–Carbon σ-Bonds of Unstrained Cyclic β-Ketoesters via Transition-Metal-Free Tandem Reactions: Synthesis of Medium-Sized Ring Compounds
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The transition-metal-free insertion of isolated alkynes into carbon–carbon σ-bonds of unstrained cyclic β-dicarbonyl compounds has been reported. These tandem reactions offer an efficient synthesis of medium-sized ring or fused-ring compounds through ring expansion. The methodology has the potential to be widely used throughout organic synthesis due to the easily accessible starting materials and mild reaction conditions.
- Zhou, Yuanyuan,Tao, Xianghua,Yao, Qiyi,Zhao, Yulei,Li, Yanzhong
-
supporting information
p. 17936 - 17939
(2016/12/16)
-
- Redox and Lewis acid relay catalysis: A titanocene/zinc catalytic platform in the development of multicomponent coupling reactions
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A titanocene-catalyzed multicomponent coupling is described herein. Using catalytic titanocene, phosphine, and zinc dust, zinc acetylides can be generated from the corresponding iodoalkynes to affect sequential nucleophilic additions to aromatic aldehydes. The intermediate propargylic alkoxides are trapped in situ with acetic anhydride, which are susceptible to a second nucleophilic displacement upon treatment with a variety of electron-rich species, including acetylides, allyl silanes, electron-rich aromatics, silyl enol ethers, and silyl ketene acetals. Additionally, employing cyclopropane carboxaldehydes led to ring-opened products resulting from iodine incorporation. Taken together, these results form the basis for a new mode of three-component coupling reactions, which allows for rapid access to value added products in a single synthetic operation.
- Gianino, Joseph B.,Campos, Catherine A.,Lepore, Antonio J.,Pinkerton, David M.,Ashfeld, Brandon L.
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p. 12083 - 12095
(2015/02/19)
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- Direct synthesis of 4-fluoroisoxazoles through gold-catalyzed cascade cyclization-fluorination of 2-alkynone O-methyl oximes
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A tandem protocol for the synthesis of fluorinated isoxazoles has been developed via catalytic intramolecular cyclizations of 2-alkynone O-methyl oximes and ensuing fluorination. The reactions proceed smoothly at room temperature in the presence of 5 mol
- Jeong, Yunkyung,Kim, Bom-I,Lee, Jae Kyun,Ryu, Jae-Sang
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p. 6444 - 6455
(2014/08/05)
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- Titanocene-catalyzed metallation of propargylic acetates in homopropargyl alcohol synthesis
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The titanium-catalyzed metallation and subsequent carbonyl addition of propargylic acetates enable the direct formation of homopropargylic alcohols in good yields. The corresponding products were obtained as single regioisomers without the corresponding a
- Meloche, Jennifer L.,Vednor, Peter T.,Gianino, Joseph B.,Oliver, Allen G.,Ashfeld, Brandon L.
-
supporting information
p. 5025 - 5028
(2015/01/09)
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- Synthesis of quinazoline based chiral ligands and application in the enantioselective addition of phenylacetylene to aldehydes
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Five novel 4-phenylquinazolinols were synthesised in three steps. Their application as ligands in the titanium tetraisopropoxide promoted catalytic enantioselective addition of phenylacetylene to a variety of aldehydes gave propargylic alcohols. Under the
- Karakaya, Idris,Karabuga, Semistan,Altundas, Ramazan,Ulukanli, Sabri
-
supporting information
p. 8385 - 8388
(2015/03/05)
-
- Catalytic asymmetric enyne addition to aldehdyes and Rh(I)-catalyzed stereoselective domino Pauson-Khand/[4 + 2] cycloaddition
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The 1,1′-bi-2-naphthol-ZnEt2-Ti(OiPr) 4-Cy2NH system is found to catalyze the 1,3-enyne addition to aliphatic aldehydes as well as other aldehydes at room temperature with 75-96% yield and 82-97% ee. This system is also broadly applicable for the highly enantioselective reaction of other alkyl-, aryl-, and silylalkynes with structurally diverse aldehydes. The propargylic alcohols prepared from the catalytic asymmetric enyne addition to aliphatic aldehydes are used to prepare a series of optically active trienynes. In the presence of a catalytic amount of [RhCl(CO)2]2 and 1 atm of CO, the optically active trienynes undergo highly stereoselective domino Pauson-Khand/[4 + 2] cycloaddition to generate optically active multicyclic products. The Rh(I) catalyst is also found to catalyze the coupling of a diyne with CO followed by [4 + 2] cycloaddition to generate an optically active multicyclic product. These transformations are potentially useful for the asymmetric synthesis of polyquinanes containing a quaternary chiral carbon center.
- Chen, Wei,Tay, Jia-Hui,Ying, Jun,Yu, Xiao-Qi,Pu, Lin
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p. 2256 - 2265
(2013/04/24)
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- Condensation of propargylic alcohols with N-methylcarbazole and carbazole in [bmim]PF6 ionic liquid; Synthesis of novel dipropargylic carbazoles using TfOH or Bi(NO3)3·5H2O as catalyst
-
A series of doubly-propargylated N-methylcarbazole and carbazole derivatives were synthesized in good to excellent isolated yields in (bmim)PF6 using triflic acid (10 mol %). The use of bismuth nitrate (20 mol %) instead of triflic acid allowed stepwise propargylation employing two different propargylic alcohols, to prepare mixed bis-propargylated carbazoles. Simple product isolation, mild reaction conditions, and repeated recycling and reuse of (bmim)PF6 are added advantages of this IL-mediated synthetic method.
- Kumar, G.G.K.S. Narayana,Laali, Kenneth K.
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supporting information
p. 965 - 969
(2013/03/13)
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- A convenient approach to β-heteroarylated (C-N bond) ketones from Cs2CO3 promoted reaction between propargyl alcohols and nitrogen-heterocycles
-
An efficient and direct approach to β-heteroarylated (C-N bond) ketones is demonstrated. Base promoted redox isomerization of propargyl alcohol to α,β-unsaturated ketone followed by conjugate addition to NH-heteroarenes affords a wide range of β-heteroarylated ketones in good to excellent yields. Aryl, heteroaryl, alkyl C(sp), and terminal alkynes containing unactivated propargyl alcohols effectively undergo redox-isomerization conjugate addition (RICA) with NH-heteroarenes. Reaction of 3-substituted pyrazoles or indazole with propargyl alcohols enables highly regioselective products. A diverse range of NH-bearing nucleophiles such as: pyrazoles, imidazole, triazoles, pyrrole, indoles and aniline participate in this reaction and deliver the corresponding β-heteroarylated ketones.
- Bhanuchandra,Kuram, Malleswara Rao,Sahoo, Akhila K.
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experimental part
p. 3538 - 3555
(2012/05/20)
-
- Enantioselective alkynylation of aldehydes with 1-haloalkynes catalyzed by tethered bis(8-quinolinato) chromium complex
-
The first example of Cr-catalyzed asymmetric alkynylation of aldehydes with 1-iodo- and 1-bromoalkynes was developed. The use of tethered bis(8-quinolinato) chromium catalyst (3 mol %) allowed preparation of enantioenriched propargyl alcohols with good yields and enantioselectivities up to 92% ee. 1-Bromoalkynes can be activated by the introduction of a cobalt porphine cocatalyst, which enables shorter reaction times without any loss of enantiocontrol.
- Usanov, Dmitry L.,Yamamoto, Hisashi
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p. 1286 - 1289
(2011/04/16)
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- Tandem amination/cycloisomerization of aryl propargylic alcohols with 2-aminopyridines as an expedient route to imidazo[1,2-a]pyridines
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A new tandem route leading to imidazo[1,2-a]pyridines has been explored through the direct amination of aryl propargylic alcohols with 2-aminopyridines and their subsequent intramolecular cycloisomerization. A ZnCl2/CuCl system has been develop
- Liu, Ping,Deng, Chun-Lin,Lei, Xinsheng,Lin, Guo-Qiang
-
experimental part
p. 7308 - 7316
(2012/01/06)
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- TBuOLi-mediated alkynylation of aldehydes
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The lithium tert-butoxide reagent was found to promote the addition of terminal aromatic alkynes to various aromatic aldehydes. This reaction was efficiently carried out in anhydrous dimethylformamide at room temperature in air for 50min, and the correspo
- Li, Chuanbin,Li, Xiaolong,Meng, Xu,Wang, Tiansheng,Li, Jihui,Chen, Baohua
-
experimental part
p. 1208 - 1217
(2011/05/04)
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- Synthesis of iodo-indoloazepinones in an iodine-mediated three-component domino reaction via a regioselective 7-endo-dig iodo-cyclization pathway ±
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An efficient and rapid synthetic strategy for the naturally occurring indoloazepinone scaffold via a three-component reaction of indole-2- carboxamides, 1,3-disubstituted propargyl alcohols, and I2 is described. The strategy involves a C-H functionalization-alkyne activation-intramolecular hydroamidation-deprotonation domino sequence. The salient feature of this sequence is regioselective electrophilic 7-endo-dig iodo-cyclization during the intramolecular hydroamidation to afford a seven-membered azepinone ring annulated to the indole.
- Sharma, Sudhir K.,Mandadapu, Anil K.,Kumar, Brijesh,Kundu, Bijoy
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experimental part
p. 6798 - 6805
(2011/10/18)
-
- Solvent-free synthesis of propargylic alcohols using zno as a new and reusable catalyst by direct addition of alkynes to aldehydes
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Under solvent-free conditions, the synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes promoted by ZnO as a novel, commercially, and cheap catalyst is described. Furthermore, the catalyst can be reused for several times w
- Hosseini-Sarvari, Mona,Mardaneh, Zahra
-
experimental part
p. 4297 - 4303
(2012/02/16)
-
- Electrophilic carbocyclization of aryl propargylic alcohols: A facile synthesis of diiodinated carbocycles and heterocycles
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Diiodinated carbocycles and oxygen heterocycles can be readily synthesized by electrophilic carbocyclization of aryl propargylic alcohols in moderate to good yields under mild conditions. The resulting diiodide can be further exploited by subsequent oxidi
- Zhu, Hai-Tao,Ji, Ke-Gong,Yang, Fang,Wang, Li-Jing,Zhao, Shu-Chun,Ali, Shaukat,Liu, Xue-Yuan,Liang, Yong-Min
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supporting information; experimental part
p. 684 - 687
(2011/05/03)
-
- Synthesis of phosphonylated and thiolated indenones by manganese(III)- mediated addition of phosphorus- and sulfur-centered radicals to 1,3-diarylpropynones
-
Phosphorus- or sulfur-centered radicals generated from the reaction of manganese(III) acetate with dialkyl phosphonates or arylthiols undergo selective additions to conjugated alkynes followed by cyclization and rearomatization to afford 2-phosphonyl- or
- Zhou, Jun,Zhang, Guang-Liang,Zou, Jian-Ping,Zhang, Wei
-
supporting information; experimental part
p. 3412 - 3415
(2011/09/12)
-
- A new and general one-pot synthesis of propargyl alcohols from esters
-
Intermediates easily prepared by partial reduction of various esters with LDBBA as a reducing agent smoothly react with lithium acetylides to give propargyl alcohols, without isolation of partial reduction intermediates, in good yields (73-83%).
- Chae, Min Jung,Jeon, Ah Ram,Livinghouse, Tom,An, Duk Keun
-
experimental part
p. 3281 - 3283
(2011/05/05)
-
- Generation of nucleophilic chromium acetylides from gem-trichloroalkanes and chromium Chloride: Synthesis of propargyl alcohols
-
Nucleophilic mixed chromium(II) and chromium(III) acetylides are generated from the smooth reduction of primary 1,1,1-trichloroalkanes with chromium(II) chloride in the presence of an excess amount of triethylamine at room temperature. These species arise from chrornium(III) vinylidene carbenoids. It has been demonstrated that uncommon low-valent CrII acetylides are formed by C-H insertion of CrIICl2 into terminal alkynes, formed in situ through the FritschButtenberg-Wiechell (FBW) rearrangement, whereas CrIII acetylides are concomitantly generated by HCl elimination from the chromium(III) vinylidene carbenoid, Both divergent pathways result, overall, in the formation of nucleophilic acetylides. In situ trapping with electrophilic aldehydes afforded propargyl alcohols. Furthermore, deuteration experiments and the use of deuterium labeled 1,1,1-trichloroalkane substrates demonstrated the prevalence of low-valent Cr11 acetylides, potentially useful, yet highly elusive synthetic intermediates.
- Dhurke, Kashinath,Steve, Tisserand,Narender, Puli,John R, Falck,Rachid, Baati
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experimental part
p. 1869 - 1874
(2010/07/18)
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- Iron-catalyzed C-O bond activation for the synthesis of propargyl-1,2,3-triazoles and 1,1-bis-triazoles
-
(Equation Presented). The FeCl3-catalyzed triazole propargylation was developed. This transformation was suitable for a large scope of substituted propargyl alcohols, giving the corresponding propargyl triazoles in excellent yields (up to 96%). Further derivatization produced the 1,1-bis-triazoles in excellent yields and regioselectivity, which could be applied as potential transition metal ligands or new reagents.
- Yan, Wuming,Wang, Qiaoyi,Chen, Yunfeng,Petersen, Jeffrey L.,Shi, Xiaodong
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supporting information; experimental part
p. 3308 - 3311
(2010/10/19)
-
- P(PhCH2NCH2CH2)3N: An efficient Lewis base catalyst for the synthesis of propargylic alcohols and Morita-Baylis-Hillman adducts via aldehyde alkynylation
-
(Chemical Equation Presented) Proazaphosphatrane P(PhCH2NCH 2CH2)3N (1a) is an efficient catalyst for the addition of aryl trimethylsilyl alkynes to a variety of aromatic, aliphatic, and heterocyclic aldehydes i
- Wadhwa, Kuldeep,Chintareddy, Venkat Reddy,Verkade, John G.
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supporting information; experimental part
p. 6681 - 6690
(2009/12/30)
-
- Catalytic enantioselective addition of terminal alkynes to aromatic aldehydes using zinc-hydroxyamide complexes
-
A mandelamide ligand, derived from (S)-mandelic acid and (S)-phenylethanamine, catalyzes the addition of aryl-, alkyl- and silyl-alkynylzinc reagents to aromatic and heteroaromatic aldehydes with good yields and good to high enantioselectivities.
- Blay, Gonzalo,Cardona, Luz,Fernandez, Isabel,Marco-Aleixandre, Alicia,Munoz, M. Carmen,Pedro, Jose R.
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scheme or table
p. 4301 - 4308
(2009/12/05)
-
- Zinc-mediated alkynylation of carbonyl compounds with iodoalkynes: a facile synthesis of propargyl alcohols
-
A straightforward synthesis of propargyl alcohols from alkynyl iodides and carbonyl compounds using zinc is described.
- Srihari,Singh, Vinay K.,Bhunia, Dinesh C.,Yadav
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scheme or table
p. 7132 - 7134
(2009/04/10)
-
- Highly enantioselective alkynylation of aldehydes catalyzed by a new oxazolidine-titanium complex
-
The readily available and inexpensive new chiral oxazolidine 2a in combination with Ti(OiPr)4 was found to catalyze the reaction of an alkynylzinc reagent with various types of aldehydes to generate chiral propargylic alcohols with high enantioselectivities (up to 95%) and excellent yields (up to 98%). The Royal Society of Chemistry.
- Xu, Zhou,Mao, Jincheng,Zhang, Yawen
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experimental part
p. 1288 - 1292
(2008/10/09)
-
- 1,1′-Binaphthyl ligands with bulky 3,3′-tertiaryalkyl substituents for the asymmetric alkyne addition to aromatic aldehydes
-
The BINOL ligand (R)-2 that contains bulky 3,3′-tertiaryalkyl groups shows improved catalytic properties over the previously reported 3,3′-substituted BINOL ligands in the asymmetric alkyne addition to aromatic aldehydes. It catalyzes the phenylacetylene
- Wang, Qin,Chen, Shan-Yong,Yu, Xiao-Qi,Pu, Lin
-
p. 4422 - 4428
(2008/02/02)
-
- Lewis base-catalyzed alkynylation of carbonyl compounds with trimethylsilylacetylenes
-
Alkynylation of carbonyl compounds with trimethylsilylacetylenes in the presence of a catalytic amount of Lewis bases such as acetate or phenoxide anion is described. The alkynylation proceeded under mild conditions and afforded the corresponding propargyl alcohols in good to excellent yields. Copyright
- Kitazawa, Takayuki,Minowa, Tomofumi,Mukaiyama, Teruaki
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p. 1002 - 1003
(2007/10/03)
-
- Carbohydrate-derived amino-alcohol ligands for asymmetric alkynylation of aldehydes
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Conformationally restricted amino alcohols based on carbohydrate scaffolds provide flexible and fine-tuneable libraries that greatly expand the range of ligands available in the Zn(OTf)2-mediated addition of alkynes to aldehydes, in some cases with very high stereoselectivities.
- Emmerson, Daniel P. G.,Hems, William P.,Davis, Benjamin G.
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p. 207 - 210
(2007/10/03)
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- Facile and convenient synthesis of functionalized propargylic alcohols and amines: An InBr3-Et3N reagent system promotes the alkynylation of aldehydes and N,O- or N,S-acetals
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The use of a novel InBr3-Et3N reagent system to promote the alkynylation of not only a variety of aromatic/heterocyclic or bulky aliphatic aldehydes but also N,O- or N,S-acetals is described. The use of N-silyl-N,O-acetals and 1-alkynes could lead to the direct production of primary propargylic amines in good yields.
- Sakai, Norio,Kanada, Reiko,Hirasawa, Maki,Konakahara, Takeo
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p. 9298 - 9304
(2007/10/03)
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- Me2Zn-mediated addition of acetylenes to aldehydes and ketones
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Contrary to expectations, commercially available 2 M Me2Zn in toluene is able to promote the addition of phenylacetylene to aldehydes and ketones. This reactivity is determined by a new, unprecedented mechanism, which involves activation of the zinc reagent via coordination with carbonyl substrates that behave "ligand like". Broad scope, high tolerance to functional groups, and a simple procedure make this new method highly interesting for the synthetic chemist.
- Cozzi, Pier Giorgio,Rudolph, Jens,Bolm, Carsten,Norrby, Per-Ola,Tomasini, Claudia
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p. 5733 - 5736
(2007/10/03)
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- BINOL-Salen-catalyzed highly enantioselective alkyne additions to aromatic aldehydes
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(Equation presented) The BINOL-Salen compound (-)-1 can catalyze the addition of both aryl- and alkylalkynes to aromatic aldehydes at room temperature with high enantioselectivity (86-97% ee). The conditions for this catalytic process are both mild and simple. Unlike most other BINOL-based catalysts, using ligand (-)-1 not only avoids heating or cooling but also does not require the addition of Ti(OiPr)4.
- Li, Zi-Bo,Pu, Lin
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p. 1065 - 1068
(2007/10/03)
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- 3,3′-Functionalized octahydro-BINOL: A facile synthesis and its high enantioselectivity in the alkyne addition to aldehydes
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A facile synthesis of an enantiomerically pure 3,3′- bismorpholinylmethyl H8-BINOL ligand has been developed. This compound in combination with Et2Zn and Ti(OiPr) 4 is found to catalyze the highly enantioselecti
- Liu, Lan,Pu, Lin
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p. 7427 - 7430
(2007/10/03)
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- InBr3-Et3N promoted alkynylation of aldehydes and N,O-acetals under mild conditions: Facile and simple preparation of propargylic alcohols and amines
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The use of a novel InBr3-Et3N reagent system to promote addition reactions of 1-alkynes not only with a variety of aromatic or bulky aliphatic aldehydes but also with N,O-acetals is described. The corresponding propargylic alcohols or amines are produced in good to excellent yields.
- Sakai, Norio,Hirasawa, Maki,Konakahara, Takeo
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p. 4171 - 4174
(2007/10/03)
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- Indium-mediated carbonyl alkynylation
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Indium mediates a Barbier-type reaction between alkynyl halides and aldehydes or ketones to give secondary or tertiary propargyl alcohols. Secondary alcohols can be oxidised in situ according an Oppenauer process.
- Augé, Jacques,Lubin-Germain, Nadège,Seghrouchni, Latifa
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p. 5255 - 5256
(2007/10/03)
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- Alkynylation of carbonyl compounds with terminal acetylenes promoted by ZnCl2 and Et3N: Simple, mild and efficient preparation of propargylic alcohols
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A mild and efficient addition of terminal acetylenes to carbonyl compounds in the presence of ZnCl2 and Et3N gives propargylic alcohols in good to high yields.
- Jiang, Biao,Si, Yu-Gui
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p. 8323 - 8325
(2007/10/03)
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