Catalytic C(sp³)-H Alkylation via an Iron Carbene Intermediate.

ABSTRACT: The catalytic transformation of a C(sp³)-H bond to a C(sp³)-C bond via an iron carbene intermediate represents a long-standing challenge. Despite the success of enzymatic and small molecule iron catalysts mediating challenging C(sp³)-H oxidations and aminations via high-valent iron oxos and nitrenes, C(sp³)-H alkylations via isoelectronic iron carbene intermediates have thus far been unsuccessful. Iron carbenes have been inert, or shown to favor olefin cyclopropanation and heteroatom-hydrogen insertion. Herein we report an iron phthalocyanine-catalyzed alkylation of allylic and benzylic C(sp³)-H bonds. Mechanistic investigations support that an electrophilic iron carbene mediates homolytic C-H cleavage and rebounds from the resulting o

SUBMITTER: Griffin JR 

PROVIDER: S-EPMC5812267 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature