Alkyl sulfinates as cross-coupling partners for programmable and stereospecific installation of C(sp³) bioisosteres.

ABSTRACT: In recent years, a variety of cycloalkyl groups with quaternary carbons, in particular cyclopropyl and cyclobutyl trifluoromethyl groups, have emerged as promising bioisosteres in drug-like molecules. The modular installation of such bioisosteres remains challenging to synthetic chemists. Alkyl sulfinate reagents have been developed as radical precursors to prepare functionalized heterocycles with the desired alkyl bioisosteres. However, the innate (radical) reactivity of this transformation poses reactivity and regioselectivity challenges for the functionalization of any aromatic or heteroaromatic scaffold. Here we showcase the ability of alkyl sulfinates to engage in sulfurane-mediated C(sp³)-C(sp²) cross-coupling, thereby allowing for programmable and stereospecifi

SUBMITTER: Zhou M 

PROVIDER: S-EPMC10838399 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature