4.8 Article

A Mild Method for Making MIDA Boronates

Journal

ORGANIC LETTERS
Volume 22, Issue 24, Pages 9408-9414

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02449

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Funding

  1. NIH [GM118185]
  2. Damon Runyon Cancer Research Foundation [DRG-2290-17]

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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.

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