Dehydrogenative Coupling of Alkylamines with Primary Alcohols Forming α‑Amino Ketones

Acceptorless dehydrogenative coupling reactions between C–H bonds offer straightforward and atom-economical methods connecting readily available materials while liberating gaseous hydrogen as the sole byproduct. Despite the growing interest in such transformations, their realization still poses a significant challenge. Here we report a photoinduced dehydrogenative coupling reaction of alkylamines with primary alcohols. C–H bonds adjacent to nitrogen and oxygen are site-selectively cleaved, and a C–C bond is created between the carbon atoms in a cross-selective manner to produce α-amino ketones. Diverse polar functionalities such as esters, amides, and carboxylic acids survived, demonstrating the broad applicability of the present method.