Carbonylation reactions of unactivated alkyl halides are a challenge and previously required the use of alkyl iodides under forcing conditions with high heat, strong irradiation, and high pressures of CO. We have developed a mild, low pressure, palladium-catalyzed alkoxycarbonylation of secondary alkyl bromides. In addition, preliminary mechanistic studies are consistent with a hybrid organometallic-radical process. This system efficiently delivers a broad range of esters from unactivated alkyl bromides across a diverse breadthe of substrates, and represents the first catalytic carbonylations of alkyl bromides with carbon monoxide.

Palladium-catalyzed alkoxycarbonylation of unactivated alkyl bromides

253rd National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.