Manipulating micellar environments for enhancing transition metal-catalyzed cross-couplings in water at room temperature

Bruce H. Lipshutz, Subir Ghorai, Wendy Wen Yi Leong, Benjamin R. Taft, Daniel V. Krogstad

Research output: Contribution to journalArticle

Abstract

The remarkable effects of added salts on the properties of aqueous micelles derived from the amphiphile PTS are described. Most notably, Heck reactions run in the presence of NaCl lead to couplings on aryl bromides in water at room temperature. Olefin cross- and ring-closing metathesis reactions run in the presence of small amounts of pH-lowering KHSO4 are also accelerated, another phenomenon that does not apply to typical processes in organic media. These salt effects allow, in general, for synthetically valuable C-C bond-forming processes to be conducted under environmentally benign conditions. Recycling of the surfactant is also demonstrated.

Original languageEnglish (US)
Pages (from-to)5061-5073
Number of pages13
JournalJournal of Organic Chemistry
Volume76
Issue number12
DOIs
StatePublished - Jun 17 2011
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

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