A Highly Chemoselective and Practical Alkynylation of Thiols

A thiol-alkynylation procedure utilizing the hypervalent iodine alkyne transfer reagent TIPS-ethynyl-benziodoxolone has been developed. This scalable reaction proceeds in five minutes at room temperature in an open flask using commercially available reagents. The scope of the reaction is broad, with a variety of phenolic, benzylic, heterocyclic, and aliphatic thiols undergoing alkynylation in excellent yield. The method is highly chemoselective as a vast array of functional groups are tolerated. The utility of the thiol-alkynylation in postsynthetic elaboration has been demonstrated through the facile installment of a fluorophore tag on a cysteine-containing peptide.


Published in:
Journal Of The American Chemical Society, 135, 26, 9620-9623
Year:
2013
Publisher:
Washington, American Chemical Society
ISSN:
0002-7863
Laboratories:




 Record created 2013-10-01, last modified 2018-09-13

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