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Synthesis of Spirocyclic Piperidines by Radical Hydroarylation.

ABSTRACT: Reported here are conditions for the construction of spirocyclic piperidines from linear aryl halide precursors. These conditions employ a strongly reducing organic photoredox catalyst in combination with a trialkylamine reductant to achieve formation of aryl radical species. Regioselective cyclization followed by hydrogen-atom transfer affords a range of complex spiropiperidines. This system operates efficiently under mild conditions without the need for toxic reagents or precious metals.

SUBMITTER: Spurlin RM

PROVIDER: S-EPMC8318207 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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Synthesis of Spirocyclic Piperidines by Radical Hydroarylation.

Spurlin Racheal M RM Harris Amber L AL Pratt Cameron J CJ Jui Nathan T NT

Synlett : accounts and rapid communications in synthetic organic chemistry 20201119 2

Reported here are conditions for the construction of spirocyclic piperidines from linear aryl halide precursors. These conditions employ a strongly reducing organic photoredox catalyst in combination with a trialkylamine reductant to achieve formation of aryl radical species. Regioselective cyclization followed by hydrogen-atom transfer affords a range of complex spiropiperidines. This system operates efficiently under mild conditions without the need for toxic reagents or precious metals. ...[more]

PMID: 34326573

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