Journal
TETRAHEDRON LETTERS
Volume 52, Issue 17, Pages 2165-2168Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.11.133
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Funding
- National Institutes of Health [GM63167]
- Eli Lilly Research Laboratories
- Johnson Johnson PRI
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The development of an effective protocol for the palladium-catalyzed cross-coupling of (E)-alkenylsilanols with aryl triflates is described. A critical component in the optimization of this method was balancing the stability and reactivity of the triflates in the presence of a nucleophilic promoter. This report highlights the use of a slightly soluble Bronsted base promoter that allows for a low, steady-state concentration of alkenyl(dimethyl)silanolate in solution, thus facilitating cross-coupling in preference to S-O bond cleavage of the triflate. (C) 2010 Elsevier Ltd. All rights reserved.
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