Remote C-H functionalization using radical translocating arylating groups.

ABSTRACT: Site selective chemical functionalization at unactivated C(sp³)-H bonds is highly challenging and recent successful studies mostly focus on the use of transition metal catalysis in combination with directing groups. Radical chemistry offers a complementary approach with the Barton and the Hofmann-Löffler-Freytag reactions being landmark contributions in the area of remote C-H functionalization at unactivated aliphatic sites. Herein we introduce the concept of radical translocation arylation at unactivated secondary and tertiary C(sp³)-H bonds in various alcohols. The straightforward two-step sequence comprises an ionic alcohol sulfonylation with especially designed ortho-iodoaryl sulfonyl chlorides followed by a radical cascade reaction including aryl radical generati

SUBMITTER: Friese FW 

PROVIDER: S-EPMC6051993 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature