Organometallic Chemistry

Branch-Selective Addition of Unactivated Olefins into Imines and Aldehydes

Authors

Abstract

Radical hydrofunctionalization occurs with ease using met-al-hydride atom transfer (MHAT) catalysis to couple alkenes and competent radicalophilic electrophiles. Traditional two-electron electrophiles have remained unreactive. Herein we report the addition of electronically-unbiased olefins into imines and aldehydes. Iron-catalysis allows addition of alkyl-substituted olefins into imines through the intermediacy of free-radicals, whereas a combination of catalytic Co(Salt-Bu,t-Bu) and chromium salts enable a branch-selective coupling of olefins and aldehydes through the formation of a putative alkyl chromium intermediate.

Content

Thumbnail image of Alkenes as carbanion surrogates - Final Draft.pdf

Supplementary material

Thumbnail image of Supporting Information FV3.pdf
Supporting Information FV3