Work

Manipulating Micellar Environments for Enhancing Transition Metal-Catalyzed Cross-Couplings in Water at Room Temperature

Year: 2011

Type: article

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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo200746y

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

Institution: University of California, Santa Barbara

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

SDG: Clean water and sanitation

Open Access status: green