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Pichette Drapeau M, Fabre I, Grimaud L, et al. Transition-Metal-Free α-Arylation of Enolizable Aryl Ketones and Mechanistic Evidence for a Radical Process. Angew Chem Int Ed Engl. 2015;54(36):10587-91doi: 10.1002/anie.201502332.
Pichette Drapeau, M., Fabre, I., Grimaud, L., Ciofini, I., Ollevier, T., & Taillefer, M. (2015). Transition-Metal-Free α-Arylation of Enolizable Aryl Ketones and Mechanistic Evidence for a Radical Process. Angewandte Chemie (International ed. in English), 54(36), 10587-91. https://doi.org/10.1002/anie.201502332
Pichette Drapeau, Martin, et al. "Transition-Metal-Free α-Arylation of Enolizable Aryl Ketones and Mechanistic Evidence for a Radical Process." Angewandte Chemie (International ed. in English) vol. 54,36 (2015): 10587-91. doi: https://doi.org/10.1002/anie.201502332
Pichette Drapeau M, Fabre I, Grimaud L, Ciofini I, Ollevier T, Taillefer M. Transition-Metal-Free α-Arylation of Enolizable Aryl Ketones and Mechanistic Evidence for a Radical Process. Angew Chem Int Ed Engl. 2015 Sep 01;54(36):10587-91. doi: 10.1002/anie.201502332. Epub 2015 Jul 01. PMID: 26136406.
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Angew Chem Int Ed Engl. 2015 Sep 01;54(36):10587-91. doi: 10.1002/anie.201502332. Epub 2015 Jul 01.

Transition-Metal-Free α-Arylation of Enolizable Aryl Ketones and Mechanistic Evidence for a Radical Process.

Angewandte Chemie (International ed. in English)

Martin Pichette Drapeau, Indira Fabre, Laurence Grimaud, Ilaria Ciofini, Thierry Ollevier, Marc Taillefer

Affiliations

  1. Institut Charles Gerhardt Montpellier, ENSCM, 8 rue de l'Ecole Normale, 34296 Montpellier (France).
  2. Département de chimie, Pavillon Alexandre-Vachon, Université Laval, 1045 avenue de la Médecine, Québec (Qc) G1V 0A6 (Canada).
  3. UPMC-ENS-CNRS-UMR 8640, Ecole Normale Supérieure, Département de chimie 24 rue Lhomond, 75231 Paris (France).
  4. Institut de Recherche de Chimie Paris, CNRS-Chimie ParisTech, 11 rue Pierre et Marie Curie, 75005 Paris (France).
  5. Institut Charles Gerhardt Montpellier, ENSCM, 8 rue de l'Ecole Normale, 34296 Montpellier (France). [email protected].

PMID: 26136406 DOI: 10.1002/anie.201502332

Abstract

The α-arylation of enolizable aryl ketones can be carried out with aryl halides under transition-metal-free conditions using KOtBu in DMF. The α-aryl ketones thus obtained can be used for step- and cost-economic syntheses of fused heterocycles and Tamoxifen. Mechanistic studies demonstrate the synergetic role of base and solvent for the initiation of the radical process.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: CC coupling; arylation; ketones; reaction mechanisms

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