A soluble polymer-supported triflating reagent: a high-throughput synthetic approach to aryl and enol triflates |
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Authors: | Wentworth A D Wentworth P Mansoor U F Janda K D |
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Institution: | Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA. |
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Abstract: | reaction: see text] The high-yielding synthesis and application of the first example of a polymer-supported reagent for the preparation of trifluoromethanesulfonates (triflates) is described. This new reagent efficiently triflates aryl alcohols and lithium enolates in high yield (>90%). A simple precipitation and filtration to remove the excess reagent and byproduct facilitate purification of the triflate products. The PEG-supported approach is highly efficient, as the PEG-supported byproduct can be quantitatively recovered and recycled into reagent 1. |
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