Allylic indiums, generated by a conjugate hydroindation of 1,3-dienes by HInCl2, reacted with carbonyl compounds in a one-pot treatment. Both γ- and α-adducts can be obtained depending upon the conditions used.
Generation of Allylic Indium by Hydroindation of 1,3-Dienes and One-Pot Reaction with Carbonyl Compounds
作者:Naoki Hayashi、Hiroyuki Honda、Makoto Yasuda、Ikuya Shibata、Akio Baba
DOI:10.1021/ol061797n
日期:2006.9.1
A hydroindation of 1,3-dienes by dichloroindium hydride (HInCl2) generates allylic indiums that react with carbonyl or imine moieties in a one-pot treatment. The former reaction proceeds in a radical manner, and the latter is ionic allylation. Moreover, both reactions require no additives such as radical initiators, Lewis acids, or transition metal catalysts.
this study, in situ catalytically generated allylic indium from 1,3 dienes and InCl2H was developed for use in the allylation of ketones. This protocol resulted in the unprecedented establishment of a successive combining of quaternary C–C bonds, which could then be applied to many types of ketones. Other branched 1,3 dienes and vinyl cyclopropanes, could also be coupled with ketones in a reaction where