Palladium-Catalyzed Heck Alkynylation of Benzyl Chlorides

Catharine H. Larsen, Kevin W. Anderson, Rachel E. Tundel, Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA, Email: sbuchwalmit.edu

C. H. Larsen, K. W. Anderson, R. E. Tundel, S. L. Buchwald, Synlett, 2006, 2941-2946.

DOI: 10.1055/s-2006-949625

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Abstract

An efficient protocol for the palladium-catalyzed Heck alkynylation using XPhos as ligand and Cs₂CO₃ as the base, couples a wide range of functionalized terminal alkynes and substituted benzyl chlorides. An excess amount of base and higher reaction temperatures allows the synthesis of allenes in a one-pot procedure.

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Key Words

palladium, alkynes, alkynylation, arylmethanes, Heck alkynylation, benzyl chlorides, allenes

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ID: J60-Y2006-4740