Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp2^2)-C(sp3^3) Cross-Couplings in Flow

Abstract

We report herein a new method for the photoredox activation of boronic esters. Using these reagents, an efficient and high-throughput continuous flow process was developed to perform a dual iridium- and nickel-catalyzed C(sp2^2)–C(sp3^3) coupling by circumventing solubility issues associated with potassium trifluoroborate salts. Formation of an adduct with a pyridine-derived Lewis base was found to be essential for the photoredox activation of the boronic esters. Based on these results we were able to develop a further simplified visible light mediated C(sp2^2)–C(sp3^3) coupling method using boronic esters and cyano heteroarenes under flow conditions.Novartis Pharma AG, Engineering and Physical Sciences Research Council (Grant IDs: EP/K0099494/1, EP/K039520/1

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