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Brahim M, Ben Ammar H, Dorcet V, et al. Palladium-Catalyzed C-H Bond Functionalization of 6,6-Diphenylfulvenes: An Easier Access to C1-Arylated and C1,C4-Diarylated Fulvenes. Org Lett. 2017;19(10):2584-2587doi: 10.1021/acs.orglett.7b00900.
Brahim, M., Ben Ammar, H., Dorcet, V., Soulé, J. F., & Doucet, H. (2017). Palladium-Catalyzed C-H Bond Functionalization of 6,6-Diphenylfulvenes: An Easier Access to C1-Arylated and C1,C4-Diarylated Fulvenes. Organic letters, 19(10), 2584-2587. https://doi.org/10.1021/acs.orglett.7b00900
Brahim, Mariem, et al. "Palladium-Catalyzed C-H Bond Functionalization of 6,6-Diphenylfulvenes: An Easier Access to C1-Arylated and C1,C4-Diarylated Fulvenes." Organic letters vol. 19,10 (2017): 2584-2587. doi: https://doi.org/10.1021/acs.orglett.7b00900
Brahim M, Ben Ammar H, Dorcet V, Soulé JF, Doucet H. Palladium-Catalyzed C-H Bond Functionalization of 6,6-Diphenylfulvenes: An Easier Access to C1-Arylated and C1,C4-Diarylated Fulvenes. Org Lett. 2017 May 19;19(10):2584-2587. doi: 10.1021/acs.orglett.7b00900. Epub 2017 May 08. PMID: 28480718.
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Org Lett. 2017 May 19;19(10):2584-2587. doi: 10.1021/acs.orglett.7b00900. Epub 2017 May 08.

Palladium-Catalyzed C-H Bond Functionalization of 6,6-Diphenylfulvenes: An Easier Access to C1-Arylated and C1,C4-Diarylated Fulvenes.

Organic letters

Mariem Brahim, Hamed Ben Ammar, Vincent Dorcet, Jean-François Soulé, Henri Doucet

Affiliations

  1. Institut des Sciences Chimiques de Rennes UMR 6226 CNRS-Université de Rennes 1 "Organométalliques: Matériaux et Catalyse", 35042 Rennes Cedex, France.
  2. Laboratoire de Synthèse Organique Asymétrique et Catalyse Homogène, (UR 11ES56), Université de Monastir , Faculté des Sciences de Monastir, avenue de l'environnement, Monastir 5000, Tunisia.

PMID: 28480718 DOI: 10.1021/acs.orglett.7b00900

Abstract

Conditions allowing the palladium-catalyzed regioselective direct arylation of fulvene derivatives are reported. The nature of the aryl source exhibits an important influence on the yield. The reaction of fulvenes with aryl bromides gave poor yields, whereas the use of benzenesulfonyl chlorides gave rise to fulvenes arylated at C1- and C4-positions on the 5-membered ring in good yields. The reaction tolerates various substituents such as nitrile, nitro, fluoro, trifluoromethyl, chloro, or even bromo on the benzenesulfonyl chloride.

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