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Lithium bis-catechol borate as an effective reductive quencher in photoredox catalysis.

ABSTRACT: The use of lithium bis-catechol borate (LiB(cat)2) as a reductive quencher for the photoredox mediated intermolecular C-H functionalization of various heteroaromatics with bromopyrroloindolines is described. LiB(cat)2 offers a financial benefit over state-of-the-art quenchers currently in use while eliminating the side reactions that typically plague these couplings. The advantage of this methodology is highlighted by the synthesis of C3-C2' (-) gliocladin C. Furthermore, additional examples of reactivity with various bromopyrroloindolines sets the stage for expedient routes towards other pharmaceutically active hexahydropyrroloindoline alkaloids and their analogues.

SUBMITTER: Sevrin MJ

PROVIDER: S-EPMC6364986 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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Lithium bis-catechol borate as an effective reductive quencher in photoredox catalysis.

Sevrin Martin J MJ Furst Laura L Nguyen John D JD Collins James L JL Stephenson Corey R J CRJ

Tetrahedron 20180418 26

The use of lithium bis-catechol borate (LiB(cat)2) as a reductive quencher for the photoredox mediated intermolecular C-H functionalization of various heteroaromatics with bromopyrroloindolines is described. LiB(cat)2 offers a financial benefit over state-of-the-art quenchers currently in use while eliminating the side reactions that typically plague these couplings. The advantage of this methodology is highlighted by the synthesis of C3-C2' (-) gliocladin C. Furthermore, a ...[more]

PMID: 30739958

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