Rapid and Modular Access to Quaternary Carbons from Tertiary Alcohols via Bimolecular Homolytic Substitution.

ABSTRACT: Quaternary carbons are ubiquitous in bioactive molecules; however, synthetic methods for the construction of this motif remain underdeveloped. Here, we report the synthesis of quaternary carbons from tertiary alcohols, a class of structurally diverse, bench-stable feedstocks, via the merger of photoredox catalysis and iron-mediated S_H2 bond formation. This alcohol-bromide cross-coupling is enabled by a novel halogen-atom transfer (XAT) reagent, which is the first reductively activated XAT reagent to be reported. A wide variety of sterically congested quaternary products can be accessed through this mild and practical protocol including products derived from both alkylation and benzylation of tertiary fragments. We further demonstrate the synthetic utility of this method through

SUBMITTER: Gould CA 

PROVIDER: S-EPMC10680126 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature