High Temperature Metalation of Functionalized Aromatics and Heteroaromatics using (tmp)₂Zn·2MgCl₂·2LiCl and Microwave Irradiation

Stefan Wunderlich and Paul Knochel*

*Department Chemie and Biochemie, Ludwig-Maximilians-Universitt, Butenandtstrasse 5−13, 81377 Munich, Germany, Email: paul.knochelcup.uni-muenchen.de

S. Wunderlich, P. Knochel, Org. Lett., 2008, 10, 4705-4707.

DOI: 10.1021/ol802118e

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Abstract

Various polyfunctional aryl and heteroaryl zinc compounds were efficiently prepared in THF via direct zincation using (tmp)₂Zn·2MgCl₂·2LiCl and microwave irradiation. Ester and cyano functions as well as ketones are tolerated. The resulting bis-organo zinc species undergo a number of coupling reactions leading to highly functionalized products in good yields.

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Key Words

Directed Ortho Metalation, Negishi Coupling, Microwave Synthesis

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ID: J54-Y2008-3150