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

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 KHSO(4) 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.

SUBMITTER: Lipshutz BH

PROVIDER: S-EPMC3608412 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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

Lipshutz Bruce H BH Ghorai Subir S Leong Wendy Wen Yi WW Taft Benjamin R BR Krogstad Daniel V DV

The Journal of organic chemistry 20110519 12

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 KHSO(4) are also accelerated, another phenomenon that does not apply to typical processes in organic media. These salt effects allow, in general, for s ...[more]

PMID: 21539384

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