Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 356, Issue 8, Pages 1767-1772Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201301023
Keywords
methoxymethyl (MOM) group; N-methyliminodiacetic acid (MIDA); MIDA boronates; ortho-phenolboronic acids; trimethylsilyl (TMS) chloride
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Funding
- National Research Foundation of Korea (NRF) - Ministry of Science, ICT and Future Planning [NRF-2013R1A1A1008434]
- Ministry of Education, NRF [NRF20100020209]
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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 degrees 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.
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