Regio- and Stereoselective Copper-Catalyzed Addition of Aromatic and Aliphatic Thiols to Terminal and Internal Nonactivated Alkynes

被引:40
|
作者
Trostyanskaya, Inna G. [1 ]
Beletskaya, Irina P. [1 ]
机构
[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia
关键词
hydrothiolation; alkynes; copper catalyst; stereoselective anti-Markovnikov addition; isomerization; CROSS-COUPLING REACTIONS; FREE-RADICAL ADDITION; VINYL SULFIDES; OXIDATIVE ADDITION; ALKENYL SULFIDES; FACILE SYNTHESIS; ENOL THIOETHERS; ARYL SULFIDES; CARBON-SULFUR; C-S;
D O I
10.1055/s-0031-1290345
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The CuI-catalyzed regio- and stereoselective hydrothiolation of terminal and internal alkynes affords (Z)-beta-alkenylsulfides. The following isomerization of the Z-isomers into E-isomers catalyzed by CuI is described.
引用
收藏
页码:535 / 540
页数:6
相关论文
共 50 条
  • [31] Copper(II)-catalyzed highly regio- and stereoselective hydrosilylation of unactivated internal alkynes with silylborate in water
    Xuan, Qing-Qing
    Ren, Chuan-Li
    Liu, Li
    Wang, Dong
    Li, Chao-Jun
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (21) : 5871 - 5874
  • [32] Regio- and stereoselective hydrosilylation of immobilized terminal alkynes
    Pedersen, Palle J.
    Henriksen, Jonas
    Gotfredsen, Charlotte H.
    Clausen, Mads H.
    [J]. TETRAHEDRON LETTERS, 2008, 49 (43) : 6220 - 6223
  • [33] Ni-Catalyzed regio- and stereoselective addition of arylboronic acids to terminal alkynes with a directing group tether
    Babu, Madala Hari
    Kumar, Gadi Ranjith
    Kant, Ruchir
    Reddy, Maddi Sridhar
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (27) : 3894 - 3897
  • [34] Rhenium-Catalyzed Regio- and Stereoselective Addition of Imines to Terminal Alkynes Leading to N-Alkylideneallylamines
    Fukumoto, Yoshiya
    Daijo, Masato
    Chatani, Naoto
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (21) : 8762 - 8765
  • [35] Copper(I)-Catalyzed Regio- and Stereoselective Silaboration of Terminal Allenes
    Ozawa, Yu
    Koriyama, Hisao
    Shiratori, Yuma
    Ito, Hajime
    [J]. ACS ORGANIC & INORGANIC AU, 2023, 3 (02): : 104 - 108
  • [36] Regio- and Stereoselective Copper-Catalyzed Allylation of 1,3-Dicarbonyl Compounds with Terminal Allenes
    Blieck, Remi
    Abdine, Racha Abed Ali
    Taillefer, Marc
    Monnier, Florian
    [J]. ORGANIC LETTERS, 2018, 20 (08) : 2232 - 2235
  • [37] Copper-Catalyzed Regio- and Enantioselective Aminoboration of Unactivated Terminal Alkenes
    Kato, Kodai
    Hirano, Koji
    Miura, Masahiro
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (22) : 5775 - 5778
  • [38] Palladium-Catalyzed Regio- and Stereoselective Chlorothiolation of Terminal Alkynes with Sulfenyl Chlorides
    Iwasaki, Masayuki
    Fujii, Tomoya
    Yamamoto, Arisa
    Nakajima, Kiyohiko
    Nishihara, Yasushi
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (01) : 58 - 62
  • [39] Regio- and stereoselective dimerization of terminal alkynes to enynes catalyzed by a palladium/imidazolium system
    Yang, CL
    Nolan, SP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02): : 591 - 593
  • [40] Copper (II)-catalyzed regio- and stereoselective addition of H/P(O)R2 to alkynes
    Trostyanskaya, Inna G.
    Beletskaya, Irina P.
    [J]. TETRAHEDRON, 2014, 70 (15) : 2556 - 2562