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A facile stereoselective synthesis of (E)-α-silylvinyl sulfides via hydromagnesiation of alkynylsilanes

✍ Scribed by Mingzhong Cai; Jun Xia; Pingping Wang

Publisher: John Wiley and Sons
Year: 2005
Tongue: English
Weight: 78 KB
Volume: 16
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.20165

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✦ Synopsis

Abstract

Hydromagnesiation of alkynylsilanes 1 in diethyl ether gave (Z)‐α‐silylvinyl Grignard reagents 2, which reacted with arylsulfenyl chlorides 3 to afford stereoselectively (E)‐α‐silylvinyl sulfides 4 in good yields. (E)‐α‐Silylvinyl sulfides 4 could undergo the cross‐coupling reactions with Grignard reagents in the presence of NiCl~2~(PPh~3~)~2~ to give stereoselectively (Z)‐1,2‐disubstituted vinylsilanes 5. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:644–647, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20165

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