Synlett 2021; 32(02): 211-214
DOI: 10.1055/a-1315-1014
cluster
Modern Heterocycle Synthesis and Functionalization

Synthesis of Spirocyclic Piperidines by Radical Hydroarylation

Racheal M. Spurlin
,
Amber L. Harris
,
Cameron J. Pratt
,
This work was funded by the National Institutes of Health (NIH, GM129495). The content is solely the responsibility of the authors and does not necessarily represent the official views of NIGMS.


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.

Supporting Information



Publication History

Received: 25 October 2020

Accepted after revision: 19 November 2020

Publication Date:
19 November 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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