Synthesis of Phenols and Aryl Silyl Ethers via Arylation of Complementary Hydroxide Surrogates

Org Lett. 2018 Apr 6;20(7):1785-1788. doi: 10.1021/acs.orglett.8b00287. Epub 2018 Mar 14.

Abstract

Two transition-metal-free methods to access substituted phenols via the arylation of silanols or hydrogen peroxide with diaryliodonium salts are presented. The complementary reactivity of the two nucleophiles allows synthesis of a broad range of phenols without competing aryne formation, as illustrated by the synthesis of the anesthetic Propofol. Furthermore, silyl-protected phenols can easily be obtained, which are suitable for further transformations.

Publication types

  • Research Support, Non-U.S. Gov't