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: lipshutzchem.ucsb.edu
B. H. Lipshutz, B. R. Taft, Org. Lett., 2008, 10, 1329-1332.
DOI: 10.1021/ol702755g (free Supporting Information)
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
B. H. Lipshutz, D. W. Chung, B. Rich, Org. Lett., 2008, 10, 3793-3796.
B. H. Lipshutz, T. B. Petersen, A. R. Abela, Org. Lett., 2008, 10, 1333-1336.
B. H. Lipshutz, G. T. Aquinaldo, S. Ghorai, K. Voigtritter, Org. Lett., 2008, 10, 1325-1328.