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

BH Lipshutz, S Ghorai, WWY Leong…

Index: Lipshutz, Bruce H.; Ghorai, Subir; Leong, Wendy Wen Yi; Taft, Benjamin R.; Krogstad, Daniel V. Journal of Organic Chemistry, 2011 , vol. 76, # 12 p. 5061 - 5073

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Citation Number: 76

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 ...