Efforts to discover and optimize new small molecule function are often impeded by limitations in synthetic access to this class of compounds. This is largely because small molecule syntheses typically employ strategies and purification methods that are highly customized for each target. We herein report a more systematized and automated approach to small molecule synthesis enabled by the iterative coupling of N-methyl iminodiacetic acid (MIDA) boronate building blocks. Building on the established capacity of this platform in accessing Csp2-rich, linear molecules, we expanded the scope of the platform to include Csp3-rich, polycyclic small molecules. Together with the discovery of a common purification method for MIDA boronate intermediates, this expansion in scope allowed for the automated synthesis of 14 distinct classes of small molecules, an important step towards the generalized automation of small molecule synthesis.

Award Address (Nobel Laureate Signature Award for Graduate Education in Chemistry sponsored by Avantor™ Performance Materials). Automated small molecule synthesis via iterative coupling of boronate building blocks

253rd National Meeting (2017)

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