General methods for synthesis of N-methyliminodiacetic acid boronates from unstable ortho-phenolboronic acids

Su Jin Ahn, Chun Young Lee, Cheol Hong Cheon

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A range of N-methyliminodiacetic acid (MIDA) boronates of commercially available but unstable ortho-phenolboronic acid derivatives can be readily prepared through simple condensation between the corresponding phenolboronic acids and MIDA in the presence of molecular sieves. The resulting MIDA boronates are bench-top stable and display a remarkable stability even in DMSO solution at high temperature (>120°C) compared with their parent boronic acids. Moreover, the utility of the resulting MIDA boronate was successfully demonstrated in a cross-coupling reaction using the slow-release protocol to afford the cross-coupled product in much better yield compared with its parent boronic acid counterpart. In addition, an alternative, but more efficient, synthetic route for difficult-to-access ortho-phenol MIDA boronates has been developed through the MIDA boronate formation of methoxymethyl (MOM) protected ortho-phenolboronic acid, followed by deprotection of the MOM group with TMSCl under ambient conditions.

Original languageEnglish
Pages (from-to)1767-1772
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume356
Issue number8
DOIs
Publication statusPublished - 2014 May 26

Keywords

  • MIDA boronates
  • N-methyliminodiacetic acid (MIDA)
  • methoxymethyl (MOM) group
  • ortho-phenolboronic acids
  • trimethylsilyl (TMS) chloride

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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