Complexation of boronic acids with a methyliminodiacetic acid (MIDA) ligand has been shown to mask the reactivity of the boron center in palladium catalyzed cross coupling, allowing the development of an iterative cross coupling platform that could perform automated synthesis of complex small molecules. This system enables non-expert participation in chemical synthesis, as the machine only requires the operator to supply the building blocks which are to be coupled. The synthesis of MIDA boronate building blocks, however, requires specialized glassware and technical expertise, especially in the case of more sensitive boronic acid starting materials. We have developed a new, complementary MIDA complexation method to take full advantage of the wide scope of commercially available boronic acids with the iterative cross coupling platform. A pre-dried form of MIDA, MIDA anhydride, was used to expand the range of boronic acids compatible with the complexation reaction, employing milder conditions and simpler procedures than existing methodology. Using MIDA anhydride, we then developed a high-throughput kit-based method for MIDA boronate synthesis to produce a wide variety of pure MIDA boronates using only heating equipment and a centrifuge.<br/>

Mild and simple method for making MIDA boronates

ACS Fall 2020 Virtual Meeting

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