Organic Chemistry Portal



Heck Couplings at Room Temperature in Nanometer Aqueous Micelles

Bruce H. Lipshutz* and Benjamin R. Taft

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

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

DOI: 10.1021/ol702755g


Aqueous Heck cross-coupling reactions of non-water-soluble partners at ambient temperatures are promoted by the nonionic amphiphiles Triton X-100 or the vitamin E-based PTS, both of which form nanomicelles in water.

see article for more examples


Development of a more recent procedure has found that using catalyst [(tBu)3P]2Pd allows for these Heck couplings to be run in < 5% PTS/water.

Bruce H. Lipshutz, July 9, 2009

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.

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.

Olefin Cross-Metathesis Reactions at Room Temperature Using the Nonionic Amphiphile “PTS”: Just Add Water

B. H. Lipshutz, G. T. Aquinaldo, S. Ghorai, K. Voigtritter, Org. Lett., 2008, 10, 1325-1328.

Key Words

Heck Reaction, Green Chemistry

ID: J54-Y2008-0880