A Soluble Polymer-Supported Triflating Reagent:  A High-Throughput Synthetic Approach to Aryl and Enol Triflates

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 fi...

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Bibliographic Details
Published inOrganic letters Vol. 2; no. 4; pp. 477 - 480
Main Authors Wentworth, Anita D, Wentworth, Paul, Mansoor, U. Faruk, Janda, Kim D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.02.2000
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Indicators and Reagents - chemistry
Mesylates - chemical synthesis
Mesylates - chemistry
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
PEG
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Summary: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.
Bibliography:Medline
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol9913237