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

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, Org. Lett., 2010, 12, 4742-4744.

DOI: 10.1021/ol101885t (free Supporting Information)


Abstract

A nonionic amphiphile (PTS) enables a simple approach to Pd-catalyzed stereoselective sp3-sp2 cross-couplings between alkyl and alkenyl bromides in the presence of zinc powder in water to give coupled products in good yields without prior formation of the organozinc reagents. The reaction is conducted at room temperature and tolerates various functional groups.

see article for more examples



Ligand Effects on Negishi Couplings of Alkenyl Halides

A. Krasovskiy, B. H. Lipshutz, Org. Lett., 2011, 13, 3818-3821.

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

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


Key Words

Negishi Coupling, Alkenes, Zinc, Green Chemistry


ID: J54-Y2010-3030