Gold(I)-mediated hydrothiolation of conjugated olefins

被引:50
作者
Brouwer, Chad [1 ]
Rahatrian, Ronald [1 ]
He, Chuan [1 ]
机构
[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
关键词
gold; homogeneous catalysis; hydrothiolation; conjugated olefin;
D O I
10.1055/s-2007-984519
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Thiol additions to conjugated olefins were catalyzed by Ph3PAuBF4 with excellent yields at room temperature. A variety of functionalized thiols. with both electron-donating and electron-withdrawing substituents, are compatible with this system. Hydrothiolations of 1.3-cyclohexadiene were also achieved in similar yields at 50 degrees C.
引用
收藏
页码:1785 / 1789
页数:5
相关论文
共 20 条
[1]   ADDITION OF THIOLS TO STYRENES - FORMATION OF BENZYLIC THIOETHERS [J].
BELLEY, M ;
ZAMBONI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (05) :1230-1232
[2]  
BROUWER M, 2006, CHEM COMMUN, V45, P1744
[3]  
GREEN TW, 1999, PROTECTIVE GROUPS OR
[5]  
Hegedus L., 1984, CATALYST POISONING
[6]   Metal-catalyzed carbon-sulfur bond formation [J].
Kondo, T ;
Mitsudo, T .
CHEMICAL REVIEWS, 2000, 100 (08) :3205-3220
[7]   Nitrene transfer reactions catalyzed by gold complexes [J].
Li, Zigang ;
Ding, Xiangyu ;
He, Chuan .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16) :5876-5880
[8]   Discovery of novel isothiazole inhibitors of the TrkA kinase: Structure-activity relationship, computer modeling, optimization, and identification of highly potent antagonists [J].
Lippa, B ;
Morris, J ;
Corbett, M ;
Kwan, TA ;
Noe, MC ;
Snow, SL ;
Gant, TG ;
Mangiaracina, M ;
Coffey, HA ;
Foster, B ;
Knauth, EA ;
Wessel, MD .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (13) :3444-3448
[9]   The first gold-catalyzed C-S bond formation:: Cycloisomerization of α-thioallenes to 2,5-dihydrothiophenes [J].
Morita, N ;
Krause, N .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (12) :1897-1899
[10]   ADDITION-REACTION OF THIOL TO OLEFIN BY USE OF TIC14 [J].
MUKAIYAMA, T ;
IZAWA, T ;
SAIGO, K ;
TAKEI, H .
CHEMISTRY LETTERS, 1973, (04) :355-356