Cross-coupling reaction of tert-alkyl halides with Grignard reagents in dichloromethane as a non-Lewis basic medium

M Ohno, K Shimizu, K Ishizaki, T Sasaki…

Index: Ohno, Masatomi; Shimizu, Kazuo; Ishizaki, Kenichi; Sasaki, Tadashi; Eguchi, Shoji Journal of Organic Chemistry, 1988 , vol. 53, # 4 p. 729 - 733

Full Text: HTML

Citation Number: 35

Abstract

In dichloromethane as a non-Lewis basic solvent, 1-haloadamantane 1 underwent a cross- coupling reaction with Grignard reagents to give bridgehead-substituted products 3-16 in moderate yields. In this case the same kind of halogen in both 1 and a Grignard reagent was favored; if not, functional exchange (ie, la to IC) occurred first. The reaction using 5- hexenylmagnesium bromide as a radical probe afforded uncyclizedfcyclized coupling ...