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Metal‐ and Oxidant‐Free Direct sp3 CH Arylation of Pyrrolidine

Metal‐ and Oxidant‐Free Direct sp3 CH Arylation of Pyrrolidine Arylated aliphatic N‐heterocycles, and particularly arylated pyrrolidines, have a wide range of applications in medicine as well as in chemistry. Arylation of pyrrolidines mainly relies on metal‐mediated couplings, which produce unwanted toxic metal waste. In this Communication, we report an oxidant‐ and metal‐free method for direct sp3 CH arylation of pyrrolidine employing a highly atom economic three‐component reaction. The method, operating under very simple and mild conditions, is highly selective and very efficient in producing single regioisomer of the arylated product even on a multigram scale. As an alternative to the metal‐mediated reaction, this method has the potential to be used in production at an industrial scale. Moreover, a new approach for CH arylation based on a novel reactivity that differs from the reactivity in Mannich or Betti reactions of iminium ion is presented. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

Metal‐ and Oxidant‐Free Direct sp3 CH Arylation of Pyrrolidine

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References (50)

Publisher
Wiley
Copyright
Copyright © 2014 Wiley Subscription Services, Inc., A Wiley Company
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201300233
Publisher site
See Article on Publisher Site

Abstract

Arylated aliphatic N‐heterocycles, and particularly arylated pyrrolidines, have a wide range of applications in medicine as well as in chemistry. Arylation of pyrrolidines mainly relies on metal‐mediated couplings, which produce unwanted toxic metal waste. In this Communication, we report an oxidant‐ and metal‐free method for direct sp3 CH arylation of pyrrolidine employing a highly atom economic three‐component reaction. The method, operating under very simple and mild conditions, is highly selective and very efficient in producing single regioisomer of the arylated product even on a multigram scale. As an alternative to the metal‐mediated reaction, this method has the potential to be used in production at an industrial scale. Moreover, a new approach for CH arylation based on a novel reactivity that differs from the reactivity in Mannich or Betti reactions of iminium ion is presented.

Journal

Asian Journal of Organic ChemistryWiley

Published: Jan 1, 2014

Keywords: ; ; ; ;

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