Efficient Aqueous-Phase Heck and Suzuki Couplings of Aryl Bromides Using Tri(4,6-dimethyl-3- sulfonatophenyl)phosphine Trisodium Salt (TXPTS)

Lucas R. Moore and Kevin H. Shaughnessy*
Department of Chemistry and the Center for Green Manufacturing, The University of Alabama, Tuscaloosa, Alabama 35487-0336
Org. Lett., 2004, 6 (2), pp 225–228
DOI: 10.1021/ol0360288
Publication Date (Web): December 23, 2003
Copyright © 2004 American Chemical Society

Abstract

Abstract Image

Sterically demanding, sulfonated arylphosphines TXPTS and TMAPTS have been applied to the aqueous-phase Heck and Suzuki coupling of aryl bromides. TXPTS provides good yields of Heck coupling products from aryl bromides at 80 °C, while both TMAPTS and TPPTS gave significantly less active catalysts. TXPTS is the first ligand to promote the aqueous-phase Heck coupling under such mild conditions. Both TXPTS and TMAPTS provide active catalysts for Suzuki couplings of aryl bromides at 50 °C.

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History

  • Published In Issue January 22, 2004
  • Received October 16, 2003

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