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Practical Heck-Mizoroki Coupling Protocol for Challenging Substrates Mediated by an N-Heterocyclic Carbene-Ligated Palladacycle

Eric Assen B. Kantchev, Guang-Rong Peh, Chi Zhang and Jackie Y. Ying*

*Institute of Bioengineering and Nanotechnology, 31 Biopolis Way, The Nanos, Singapore 138669, Singapore, Email: jyyingibn.a-star.edu.sg

E. A. B. Kantchev, G.-R. Peh, C. Zhang, J. Y. Ying, Org. Lett., 2008, 10, 3949-3952.

DOI: 10.1021/ol8012809 (free Supporting Information)


Abstract

A highly active, N-heterocyclic carbene-palladacycle precatalyst for the Heck-Mizoroki reaction can be synthesized on a large scale in excellent yield and is tolerant to air, moisture, and long-term storage. A wide range of challenging substrates is successfully coupled under a simple and user-friendly reaction protocol.

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Note

The catalyst performs equally well using non-oxygen free solvents under air atmosphere. The higher yield for 2,6-dimethoxy-1-iodobenzene is due to an improved purification procedure applied during the "in air" run - see Supporting Information file for details.

E. A. B. Kantchev, January 21, 2010


Key Words

Heck Reaction


ID: J54-Y2008-2510