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

Bruce H. Lipshutz,* Tue B. Petersen and Alexander R. Abela

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

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

DOI: 10.1021/ol702714y (free Supporting Information)


Abstract

Use of a dilute aqueous solution of a nonionic amphiphile allows efficient Suzuki-Miyaura cross-couplings of arylboronic acids with a broad range of aryl halides and pseudohalides, including sterically hindered and lipophilic substrates, in most cases at room temperature.

see article for more examples



Micellar Catalysis of Suzuki-Miyaura Cross-Couplings with Heteroaromatics in Water

B. H. Lipshutz, A. R. Abela, Org. Lett., 2008, 10, 5329-5332.

Heck Couplings at Room Temperature in Nanometer Aqueous Micelles

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

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

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


Key Words

Suzuki Coupling, Green Chemistry


ID: J54-Y2008-0910