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Sonogashira Couplings of Aryl Bromides: Room Temperature, Water Only, No Copper

Bruce H. Lipshutz*, David W. Chung and Brian Rich

*Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, Email:

B. H. Lipshutz, D. W. Chung, B. Rich, Org. Lett., 2008, 10, 3793-3796.

DOI: 10.1021/ol801471f (free Supporting Information)

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Small amounts of the nonionic amphiphile PTS assist by virtue of nanometer micelles formed spontaneously in cross-coupling reactions between lipophilic terminal alkynes and aryl bromides catalyzed by ligated Pd in the absence of copper at ambient temperatures.

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Heck Couplings at Room Temperature in Nanometer Aqueous Micelles

B. H. Lipshutz, B. R. Taft, Org. Lett., 2008, 10, 1329-1332.

Room-Temperature Suzuki-Miyaura Couplings in Water Facilitated by Nonionic Amphiphiles

B. H. Lipshutz, T. B. Petersen, A. R. Abela, Org. Lett., 2008, 10, 1333-1336.

Key Words

Sonogashira Coupling, Green Chemistry

ID: J54-Y2008-2350