Protodeboronation of ortho- and para-phenol boronic acids and application to ortho and meta functionalization of phenols using boronic acids as blocking and directing groups

Chun Young Lee, Su Jin Ahn, Cheol Hong Cheon

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

The first metal-free thermal protodeboronation of ortho- and para-phenol boronic acids in DMSO was developed. The protodeboronation was successfully applied to the synthesis of ortho- and meta-functionalized phenols using the boronic acid moiety as a blocking group and a directing group, respectively. Mechanistic studies suggested that this protodeboronation proceeds through the coordination of water to the boron atom followed by σ-bond metathesis.

Original languageEnglish
Pages (from-to)12154-12160
Number of pages7
JournalJournal of Organic Chemistry
Volume78
Issue number23
DOIs
Publication statusPublished - 2013 Dec 6

ASJC Scopus subject areas

  • Organic Chemistry

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