En Route to Direct Cross-Coupling between Carbonyl Derivatives and Allyl Alcohols via Hydrazones

Abstract

Allylic cross-couplings are pivotal in the organic chemistry toolbox; however, traditional methods require the extensive use of noble metals and are limited to activated substrates. To date, allylic cross-couplings that utilize affordable metals and unactivated allylic alcohols remain unexplored. Herein, we report a distinct coupling of ubiquitous and commercially available aldehydes with unactivated allyl alcohols, which also benefits from generating only water and nitrogen gas as innocuous byproducts. This operationally simple and mild methodology enables the direct allylation of carbonyl derivatives, affording alkene products in moderate to high yields across 40 substrates. The reported conditions tolerate both aryl and alkyl aldehydes, as well as ketones with a variety of functional groups. Notably, our strategy facilitates the expedited synthesis of value-added chemicals while producing environmentally benign byproducts.