Zn-Mediated, Pd-Catalyzed Cross-Couplings in Water at Room Temperature Without Prior Formation of Organozinc Reagents

Arkady Krasovskiy, Christophe Duplais and Bruce H. Lipshutz*

*Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, Email: lipshutzchem.ucsb.edu

A. Krasovskiy, C. Duplais, B. H. Lipshutz, J. Am. Chem. Soc., 2009, 131, 15592-15593.

DOI: 10.1021/ja906803t

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Abstract

A simple approach to Pd-catalyzed sp³-sp² cross-couplings between alkyl iodides and aryl bromides in the presence of zinc powder in water is enabled by a nonionic amphiphile, to give the alkylated aromatics in good yields. The reaction is conducted at room temperature and tolerates various functional groups.

see article for more examples

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Stereoselective Negishi-like Couplings Between Alkenyl and Alkyl Halides in Water at Room Temperature

A. Krasovskiy, C. Duplais, B. H. Lipshutz, Org. Lett., 2010, 12, 4742-4744.

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Key Words

Negishi Coupling, Arenes, Zinc, Green Chemistry

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ID: J48-Y2009-3190