- Manipulating micellar environments for enhancing transition metal-catalyzed cross-couplings in water at room temperature
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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.
- Lipshutz, Bruce H.,Ghorai, Subir,Leong, Wendy Wen Yi,Taft, Benjamin R.,Krogstad, Daniel V.
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experimental part
p. 5061 - 5073
(2011/08/06)
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- Tandem olefin metathesis-elimination reactions. A new route to doubly unsaturated carbonyl derivatives
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Cross-metathesis between an activated olefin and an ethereal derivative of homoallylic alcohols leads to products that are subject to facile elimination resulting in α,β,γ,δ-unsaturated esters, ketones, acids, and aldehydes in high yields.
- Lipshutz, Bruce H.,Ghorai, Subir,Bo?kovi?, ?arko V.
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p. 6949 - 6954
(2008/09/20)
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