Divergent regioselective Heck-type reaction of unactivated alkenes and N-fluoro-sulfonamides.

ABSTRACT: The control of regioselectivity in Heck-type reaction of unactivated alkenes represents a longstanding challenge due to several detachable hydrogens in β-H elimination step, which generally afford either one specific regioisomer or a mixture. Herein, a copper-catalyzed intermolecular Heck-type reaction of unactivated alkenes and N-fluoro-sulfonamides with divergent regioselectivities is reported. The complete switch of regioselectivity mainly depends on the choice of different additives. Employment of alcohol solvent gives access to vinyl products, while the addition of carboxylate leads to the formation of allylic products. In addition, exclusion of these two promoting factors results in β-lactams via a C-N reductive elimination. This protocol shows a broad substrate scope for both alkene

SUBMITTER: Zhao C 

PROVIDER: S-EPMC9588056 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature