Synthesis of Spirocyclic Piperidines by Radical Hydroarylation | Zendy

Racheal M. Spurlin | Zendy; Amber L. Harris | Zendy; Nathan T. Jui | Zendy; Cameron J. Pratt | Zendy

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Synthesis of Spirocyclic Piperidines by Radical Hydroarylation

Author(s) -

Racheal M. Spurlin,

Amber L. Harris,

Nathan T. Jui,

Cameron J. Pratt

Publication year - 2020

Publication title -

synlett

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.712

H-Index - 133

eISSN - 1437-2096

pISSN - 0936-5214

DOI - 10.1055/a-1315-1014

Subject(s) - chemistry , regioselectivity , reagent , aryl , halide , catalysis , hydrogen atom , combinatorial chemistry , aryl radical , photoredox catalysis , organic chemistry , photochemistry , alkyl , photocatalysis

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.

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