Abstract
The classical Heck reaction is among the most powerful methods available for the construction
of C–C bonds. Modification of this transformation to utilize diverse organohalide
coupling partners has resulted in new reactions such as the silyl-Heck, aza-Heck,
and boryl-Heck reactions. In contrast, modification of the olefin coupling partner
is rare. For instance, use of the π-bond of an aldehyde instead of an alkene would
provide ketones via a carbonyl-Heck process. This seemingly minor manipulation of
the Heck reaction has proven surprisingly difficult to realize in practice. Through
the use of high-throughput experimentation techniques, an efficient catalyst system
for this transformation was identified, enabling the intermolecular coupling of organotriflates
and aldehydes to synthesize diverse ketones.
Key words
Heck reaction - cross-coupling - nickel - high-throughput experimentation - reaction
discovery
