镍催化新戊基芳基磺酸酯与甲基和伯烷基溴化镁的交叉偶联反应。

Nickel-catalyzed cross-coupling of neopentyl arenesulfonates with methyl and primary alkylmagnesium bromides.

作者信息

Cho Chul-Hee, Sun Myungchul, Seo Yong-Seok, Kim Chul-Bae, Park Kwangyong

机构信息

Department of Chemical Engineering, Chung-Ang University, Heukseok-dong 221, Dongjak-gu, Seoul 156-756, South Korea.

出版信息

J Org Chem. 2005 Feb 18;70(4):1482-5. doi: 10.1021/jo048300c.

DOI:10.1021/jo048300c

PMID:15704991

Abstract

[reaction: see text] Neopentyl arenesulfonates were reacted with methyl and primary alkylmagnesium bromides in the presence of dppeNiCl(2), via the nucleophilic aromatic substitution of neopentyloxysulfonyl groups by the primary alkyl nucleophiles, to produce the corresponding alkylarenes in good yields. This result shows that the alkyloxysulfonyl group might be a suitable alternative to halides and triflate in some circumstances.

摘要

[反应：见正文] 新戊基芳基磺酸盐在dppeNiCl₂存在下与甲基和伯烷基溴化镁反应，通过伯烷基亲核试剂对新戊氧基磺酰基的亲核芳香取代反应，以良好的产率生成相应的烷基芳烃。该结果表明，在某些情况下，烷氧基磺酰基可能是卤化物和三氟甲磺酸盐的合适替代物。