Lewis Acid–Base Interaction-Controlled ortho-Selective C−H Borylation of Aryl Sulfides

Hong Liang Li, Yoichiro Kuninobu, Motomu Kanai

Research output: Contribution to journalArticlepeer-review

63 Citations (Scopus)

Abstract

An iridium/bipyridine-catalyzed ortho-selective C−H borylation of aryl sulfides was developed. High ortho-selectivity was achieved by a Lewis acid–base interaction between a boryl group of the ligand and a sulfur atom of the substrate. This is the first example of a catalytic and regioselective C−H transformation controlled by a Lewis acid–base interaction between a ligand and a substrate. The C−H borylation reaction could be conducted on a gram scale, and with a bioactive molecule as a substrate, demonstrating its applicability to late-stage regioselective C−H borylation. A bioactive molecule was synthesized from an ortho-borylated product by converting the boryl and methylthio groups of the product.

Original languageEnglish
Pages (from-to)1495-1499
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number6
DOIs
Publication statusPublished - Feb 2017
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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