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.