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A Mild Negishi Cross-Coupling of 2-Heterocyclic Organozinc Reagents and Aryl Chlorides

Michael R. Luzung*, Jigar S. Patel and Jingjun Yin*

*Department of Process Research, Merck Research Laboratories, P.O. Box 2000 Rahway, New Jersey 07065, United States, Email: michael_luzungmerck.com, jingjun_yinmerck.com

M. R. Luzung, J. S. Patel, J. Yin, J. Org. Chem., 2010, 75, 8330-8332.

DOI: 10.1021/jo1018798 (free Supporting Information)


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Abstract

The use of Pd2(dba)3 and X-Phos as a ligand enables a mild Negishi cross-coupling of 2-heterocyclic organozinc reagents and aryl chlorides providing 2-aryl-substituted pyridines and thiophenes in high yields. An efficient method to generate the organozinc reagents at room temperature is also demonstrated.

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Key Words

Pyridines, Negishi Coupling, Heterobiaryls


ID: J42-Y2010-3510