Open AccessSynthesis of Spirocyclic Piperidines by Radical Hydroarylation
Author(s) -
Racheal M. Spurlin,
Amber L. Harris,
Cameron J. Pratt,
Nathan T. Jui
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.