Stereoselective Formation of Z- or E-Vinyl Thioethers from Arylthiols and Acetylenes under Transition-Metal-Free Conditions

被引：22

作者：

Liao, Yunfeng ^{[1
,2
]}

Chen, Shanping ^{[1
]}

Jiang, Pengcheng ^{[1
]}

Qi, Hongrui ^{[1
]}

Deng, Guo-Jun ^{[1
]}

机构：

[1] Xiangtan Univ, Key Lab Environm Friendly Chem & Applicat, Minist Educ, Coll Chem, Xiangtan 411105, Peoples R China

[2] Hunan Inst Engn, Sch Chem & Chem Engn, Xiangtan 411104, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 30期

基金：

高等学校博士学科点专项科研基金; 中国国家自然科学基金;

关键词：

Vinylic compounds; Thiols; Alkynes; Regioselectivity; Diastereoselectivity; CATALYZED ALKYNE HYDROTHIOLATION; MEDIATED HYDROTHIOLATION; TERMINAL ALKYNES; SULFIDES; THIOLS; ADDITIONS; STEREOCHEMISTRY; COMPLEXES; OLEFINS; FACILE;

D O I：

10.1002/ejoc.201300727

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vinyl sulfide formation with good yield and high regio- and stereoselectivities from thiols and acetylenes under transition-metal-free conditions is described. Potassium phosphate was used as an effective additive to enhance the reaction yield and selectivity. Z-Vinyl sulfides were predominately formed in the presence of potassium phosphate, whereas E-vinyl sulfides were formed under solvent- and base-free conditions.

引用

页码：6878 / 6885

页数：8

共 44 条

[1]

BALIAH V, 1971, INDIAN J CHEM, V9, P220

[2] Water-promoted regioselective hydrothiolation of alkynes [J].

Bhadra, Sukalyan ;

Ranu, Brindaban C. .

CANADIAN JOURNAL OF CHEMISTRY, 2009, 87 (11) :1605-1609

[3] Rhodium-catalyzed alkyne hydrothiolation with aromatic and aliphatic thiols [J].

Cao, CS ;

Fraser, LR ;

Love, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (50) :17614-17615

[4] The Emergence of Transition-Metal-Mediated Hydrothiolation of Unsaturated Carbon-Carbon Bonds: A Mechanistic Outlook [J].

Castarlenas, Ricardo ;

Di Giuseppe, Andrea ;

Perez-Torrente, Jesus J. ;

Oro, Luis A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (01) :211-222

[5] Efficient synthesis of vinyl and alkyl sulfides via hydrothiolation of alkynes and electron-deficient olefins using soluble and heterogenized gold complexes catalysts [J].

Corma, Avelino ;

Gonzalez-Arellano, Camino ;

Iglesias, Marta ;

Sanchez, Felix .

APPLIED CATALYSIS A-GENERAL, 2010, 375 (01) :49-54

[6]

Cremlyn RJ., 1996, An introduction to organosulfur chemistry

[7] Facile, efficient routes to diverse protected thiols and to their deprotection and addition to create functional polymers by thiol-ene coupling [J].

David, R. L. Ameri ;

Kornfield, Julia A. .

MACROMOLECULES, 2008, 41 (04) :1151-1161

[8] Ligand-Controlled Regioselectivity in the Hydrothiolation of Alkynes by Rhodium N-Heterocyclic Carbene Catalysts [J].

Di Giuseppe, Andrea ;

Castarlenas, Ricardo ;

Perez-Torrente, Jesus J. ;

Crucianelli, Marcello ;

Polo, Victor ;

Sancho, Rodrigo ;

Lahoz, Fernando J. ;

Oro, Luis A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (19) :8171-8183

[9]

Drabowicz J., 2007, SCI SYNTHESIS HOUBEN, V33, P113

[10]

Dvorak C. A., 2000, ANGEW CHEM, V112, P1730

← 1 2 3 4 5 →