Indium-catalyzed addition of carbon units to acetylenes: Development of a new C-C bond formation toward exploitation of chemical resources*
Masaharu Nakamura
Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
Abstract: This account deals with an overview of the development of catalytic addition reactions of carbonyl compounds to alkynes catalyzed by a variety of indium salts. The new C-C bond formation reactions provide a powerful tool for α-functionalization of carbonyl compounds, including direct α-vinylation with acetylene, regioselective α-alkenylation, and α-ynenylation that can be applied to a modular synthesis of α-arylated β-keto esters.
Keywords: carbon-carbon bond formation; indium catalyst; carbonyl compounds; alkenylation; carbometallation.
*Pure Appl. Chem. 78, 197-523. An issue of reviews and research papers based on lectures presented at the 13th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-13), Geneva, Switzerland, 17-21 July 2005.