Tandem Pd/Au-Catalyzed Route to α-Sulfenylated Carbonyl Compounds from Terminal Propargylic Alcohols and Thiols

被引：25
作者：
Biswas, Srijit [1 ]
Watile, Rahul A. [1 ]
Samec, Joseph S. M. [1 ]
机构：
[1] Uppsala Univ, Dept Chem, BMC, S-75123 Uppsala, Sweden
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 08期
基金：
瑞典研究理事会;
关键词：
atom efficiency; gold; palladium; sulfenylated carbonyl; tandem catalysis; ENANTIOSELECTIVE SULFENYLATION; ASYMMETRIC SULFENYLATION; GOLD CATALYSIS; PALLADIUM; SULFUR; VINYL; HYDROTHIOLATION; REARRANGEMENT; ACTIVATION; REACTIVITY;
D O I：
10.1002/chem.201304111
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient and highly atom-economical tandem Pd/Au-catalyzed route to -sulfenylated carbonyl compounds from terminal propargylic alcohols and thiols has been developed. This one-step procedure has a wide substrate scope with respect to substituents at the -position of the alcohol. Both aromatic and aliphatic thiols generated the -sulfenylated carbonyl products in good to excellent yields. A mechanism is proposed in which the reaction proceeds through a Pd-catalyzed regioselective hydrothiolation at the terminal triple bond of the propargyl alcohol followed by an Au-catalyzed 1,2-hydride migration.
引用
收藏
页码：2159 / 2163
页数：5
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