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Profiling and Application of Photoredox C(sp 3 )-C(sp 2 ) Cross-Coupling in Medicinal Chemistry.

Recent visible-light photoredox catalyzed C(sp3 )-C(sp2 ) cross-coupling provides a novel transformation to potentially enable the synthesis of medicinal chemistry targets. Here, we report a profiling study of photocatalytic C(sp3 )-C(sp2 ) cross-coupling, both decarboxylative coupling and cross-electrophile coupling, with 18 pharmaceutically relevant aryl halides by using either Kessil lamp or our newly developed integrated photoreactor. Integrated photoreactor accelerates reaction rate and improves reaction success rate. Cross-electrophile coupling gives higher success rate with broad substrate scope on alkyl halides than that of the decarboxylative coupling. In addition, a successful application example on a discovery program demonstrates the efficient synthesis of medicinal chemistry targets via photocatalytic C(sp3 )-C(sp2 ) cross-coupling by using our integrated photoreactor.

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