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

34 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

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Boronic Acids
Phenols
Phenol
Boron
Dimethyl Sulfoxide
Hot Temperature
Metals
Atoms
Water

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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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.",
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