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Profiling and Application of Photoredox C(sp³)-C(sp²) Cross-Coupling in Medicinal Chemistry.

ABSTRACT: 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.

SUBMITTER: Zhang R

PROVIDER: S-EPMC6047024 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Profiling and Application of Photoredox C(sp3)-C(sp2) Cross-Coupling in Medicinal Chemistry.

Zhang Rui R Li Guoqing G Wismer Michael M Vachal Petr P Colletti Steven L SL Shi Zhi-Cai ZC

ACS medicinal chemistry letters 20180507 7

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 photor ...[more]

PMID: 30034617

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