Microwave-mediated synthesis of N-methyliminodiacetic acid (MIDA) boronates

Abstract

(2014) Microwavemediated synthesis of N-methyliminodiacetic acid (MIDA) boronates. Tetrahedron, 70 (47). pp. [9125][9126][9127][9128][9129][9130][9131] This version is available from Sussex Research Online: http://sro.sussex.ac.uk/53847/ This document is made available in accordance with publisher policies and may differ from the published version or from the version of record. If you wish to cite this item you are advised to consult the publisher's version. Please see the URL above for details on accessing the published version. Copyright and reuse:Sussex Research Online is a digital repository of the research output of the University.Copyright and all moral rights to the version of the paper presented here belong to the individual author(s) and/or other copyright owners. To the extent reasonable and practicable, the material made available in SRO has been checked for eligibility before being made available.Copies of full text items generally can be reproduced, displayed or performed and given to third parties in any format or medium for personal research or study, educational, or not-for-profit purposes without prior permission or charge, provided that the authors, title and full bibliographic details are credited, a hyperlink and/or URL is given for the original metadata page and the content is not changed in any way. ABSTRACT: A library of over twenty, mainly aryl or heteroaryl, N-methyliminodiacetic acid (MIDA) boronates has been synthesized. A rapid microwave-mediated (MW) method (5-10 mins) has been developed using polyethylene glycol 300 (PEG 300) as solvent. However, acetonitrile (MeCN) and dimethylformamide (DMF) were found to be alternative solvents, the latter especially for 2-substituted aryl boronic acids.

Recent Advances in Methylation: A Guide for Selecting Methylation Reagents

“…Recently, the synthesis of B ‐methyl MIDA boronate ( 177 , Scheme ) has been reported . This tetrahedral boronate is less prone to transmetallation than MeBF 3 K under Suzuki conditions .…”

Ene reactions of 2-borylated α-methylstyrenes: a practical route to 4-methylenechromanes and derivatives

“…The spectroscopic data match with those reported in the literature. 40 Bromo-6-fluorophenyl)-6-methyl-1,3,6,2dioxazaborocane-4,8-dione (6g) White solid, 851 mg, 86%; mp 214-216 °C; 1 Please do not adjust margins Please do not adjust margins 1H), 4.13 (d, J = 17.1, 2H), 3.97 (d, J = 17.1, 2H), 2.78 (s, 3H). 13 C NMR (75 MHz, Acetonitrile-d3, δ ppm) 169.…”

“…The spectroscopic data match with those reported in the literature. 40 Bromo-4-methylphenyl)-6-methyl-1,3,6,2dioxazaborocane-4,8-dione (6h) White solid, 851 mg, 87%; mp 230-232 °C; 1 2.32 (s, 3H). 13 C NMR (75 MHz, Acetonitrile-d3, δ ppm) 169.…”

Combinatorial Chemistry Online Volume 17, Issue 1, January 2015

“…A rapid microwave-mediated method (5-10 min) has been developed using polyethylene glycol 300 as solvent, although acetonitrile and dimethylformamide were found to be suitable alternative solvents [3].…”