Hypervalent Iodine(III)-Mediated Tosyloxylation of 4-Hydroxycoumarins

J Org Chem. 2019 Aug 16;84(16):10136-10144. doi: 10.1021/acs.joc.9b01323. Epub 2019 Jun 25.

Abstract

An efficient approach was developed for synthesis of 3-tosyloxy-4-hydroxycoumarins under mild conditions by using Koser's reagents. The reaction tolerated various functional groups, and the products served as useful aromatic building blocks. Additionally, a plausible mechanism via iodonium ylide was proposed, and the oral anticoagulant Warfarin was synthesized in good yield.

Publication types

  • Research Support, Non-U.S. Gov't