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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:

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

DOI: 10.1021/ol802118e

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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

ID: J54-Y2008-3150