Addition of s-h bonds across electron-deficient olefins catalyzed by well-defined copper(I) thiolate complexes

被引:83
作者
Delp, Samuel A.
Munro-Leighton, Colleen
Goj, Laurel A.
Ramirez, Magaly A.
Gunnoe, T. Brent
Petersen, Jeffrey L.
Boyle, Paul D.
机构
[1] N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
[2] W Virginia Univ, C Eugene Bennett Dept Chem, Morgantown, WV 26506 USA
关键词
D O I
10.1021/ic070268s
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of monomeric (NHC)Cu(SR) (R = Ph or CH2Ph; NHC = N-heterocyclic carbene) complexes have been synthesized and fully characterized including single-crystal X-ray diffraction studies. These complexes catalyze the addition of S-H bonds across electron-deficient olefins to regioselectively produce "anti-Markovnikov" products.
引用
收藏
页码:2365 / 2367
页数:3
相关论文
共 34 条
[1]   Synthesis of thiiranes by direct sulfur transfer: The challenge of developing effective sulfur donors and metal catalysts [J].
Adam, W ;
Bargon, RM .
CHEMICAL REVIEWS, 2004, 104 (01) :251-261
[2]   Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[3]   Sequential one-pot InBr3-catalyzed 1,4-then 1,2-nucleophilic addition to enones [J].
Bandini, M ;
Cozzi, PG ;
Giacomini, M ;
Melchiorre, P ;
Selva, S ;
Umani-Ronchi, A .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) :3700-3704
[4]   Synthesis, solid-state crystal structure, and reactivity of a monomeric copper(I) anilido complex [J].
Blue, ED ;
Davis, A ;
Conner, D ;
Gunnoe, TB ;
Boyle, PD ;
White, PS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (31) :9435-9441
[5]   Electrochemical synthesis and structural characterization of the trinuclear copper(I)-copper(II) complex: bis[bis(triphenylphosphine)copper(I)] [bis(thiosalicylate)copper(II)] [J].
Bott, RC ;
Healy, PC ;
Sagatys, DS .
CHEMICAL COMMUNICATIONS, 1998, (21) :2403-2404
[6]   A study of the conjugate addition of thionucleophiles to 2(5H)-furanones [J].
Busqué, F ;
de March, P ;
Figueredo, M ;
Font, J ;
González, L .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (07) :1492-1499
[7]   A rising drug industry [J].
Daemmrich, AA ;
Bowden, ME .
CHEMICAL & ENGINEERING NEWS, 2005, 83 (25) :28-+
[8]   A catalytic Michael addition of thiols to α,β-unsaturated carbonyl compounds:: Asymmetric Michael additions and asymmetric protonations [J].
Emori, E ;
Arai, T ;
Sasai, H ;
Shibasaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :4043-4044
[9]   Iodine catalyzed conjugate addition of mercaptans to α,β-unsaturated carboxylic acids under solvent-free condition [J].
Gao, SJ ;
Tzeng, TK ;
Sastry, MNV ;
Chu, CM ;
Liu, JT ;
Lin, CC ;
Yao, CF .
TETRAHEDRON LETTERS, 2006, 47 (12) :1889-1893
[10]   Copper(II) tetrafluoroborate as a novel and highly efficient catalyst for Michael addition of mercaptans to α,β-unsaturated carbonyl compounds [J].
Garg, SK ;
Kumar, R ;
Chakraborti, AK .
TETRAHEDRON LETTERS, 2005, 46 (10) :1721-1724