Reductive radical-initiated 1,2-C migration assisted by an azidyl group.

ABSTRACT: We report here a novel reductive radical-polar crossover reaction that is a reductive radical-initiated 1,2-C migration of 2-azido allyl alcohols enabled by an azidyl group. The reaction tolerates diverse migrating groups, such as alkyl, alkenyl, and aryl groups, allowing access to n+1 ring expansion of small to large rings. The possibility of directly using propargyl alcohols in one-pot is also described. Mechanistic studies indicated that an azidyl group is a good leaving group and provides a driving force for the 1,2-C migration.

SUBMITTER: Zhang X 

PROVIDER: S-EPMC8163324 | biostudies-literature |

REPOSITORIES: biostudies-literature