Synthesis of aryl ethers via a sulfonyl transfer reaction

Org Lett. 2012 Aug 3;14(15):3886-9. doi: 10.1021/ol301615z. Epub 2012 Jul 17.

Abstract

A general synthesis of aryl ethers from primary and secondary alcohols and aryl mesylates is presented. The reaction proceeds via a sulfonyl-transfer mechanism. In this paper, we compare the sulfonyl transfer reaction to Mitsunobu ether formation. The reaction can be employed in a multistep synthesis where the aryl mesylate is used as a phenol protecting group and then as an activating group for ether formation. This protecting/activating group strategy is demonstrated using raloxifene as the target.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Ethers / chemical synthesis*
  • Ethers / chemistry
  • Mesylates / chemistry*
  • Molecular Structure
  • Phenols / chemical synthesis
  • Raloxifene Hydrochloride / chemical synthesis*
  • Raloxifene Hydrochloride / chemistry
  • Structure-Activity Relationship

Substances

  • Alcohols
  • Ethers
  • Mesylates
  • Phenols
  • methanesulfonic acid
  • Raloxifene Hydrochloride