Formal C-H/C-I Metathesis: Site-Selective C-H Iodination of 2-Aryl Benzoic Acid Derivatives Using Aryl Iodide

Org Lett. 2022 Jun 10;24(22):3926-3931. doi: 10.1021/acs.orglett.2c01224. Epub 2022 May 31.

Abstract

C-H functionalization via functional group metathesis is extremely rare. A protocol of remote site-selective C-H iodination of 2-aryl benzoic acid derivatives via formal C(sp2)-H/C(sp2)-I metathesis using readily available 1-iodo-4-methoxy-2-nitrobenzene as the mild iodinating reagent was reported herein. A range of 2-aryl benzoic acid derivatives including 2-(naphthalen-1-yl)benzoic acids and [1,1'-binaphthalene]-2-carboxylic acids were iodinated under mild conditions to give valuable iodinated products in a site- and chemo-selective fashion.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoates
  • Benzoic Acid*
  • Catalysis
  • Halogenation*
  • Iodides

Substances

  • Benzoates
  • Iodides
  • Benzoic Acid