Contra-thermodynamic Olefin Isomerization by Chain-Walking Hydroboration and Dehydroboration.

ABSTRACT: We report a dehydroboration process that can be coupled with chain-walking hydroboration to create a one-pot, contra-thermodynamic, short- or long-range isomerization of internal olefins to terminal olefins. This dehydroboration occurs by a sequence comprising activation with a nucleophile, iodination, and base-promoted elimination. The isomerization proceeds at room temperature without the need for a fluoride base, and the substrate scope of this isomerization is expanded over those of previous isomerizations we have reported with silanes.

SUBMITTER: Hanna S 

PROVIDER: S-EPMC8931855 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature