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 language | English |
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Pages (from-to) | 1767-1772 |
Number of pages | 6 |
Journal | Advanced Synthesis and Catalysis |
Volume | 356 |
Issue number | 8 |
DOIs | |
Publication status | Published - 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