A Mild Method for Making MIDA Boronates

We disclose that a predried form of methyliminodiacetic acid (MIDA), MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into th...

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Veröffentlicht in:Organic letters 2020-12, Vol.22 (24), p.9408-9414
Hauptverfasser: Kelly, Aidan M, Chen, Peng-Jui, Klubnick, Jenna, Blair, Daniel J, Burke, Martin D
Format: Artikel
Sprache:eng
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Zusammenfassung:We disclose that a predried form of methyliminodiacetic acid (MIDA), MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, we have developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in laboratories that do not specialize in organic synthesis.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02449