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Zhao Q, Tognetti V, Joubert L, et al. Palladium-Catalyzed Synthesis of 3-Trifluoromethyl-Substituted 1,3-Butadienes by Means of Directed C-H Bond Functionalization. Org Lett. 2017;19(8):2106-2109doi: 10.1021/acs.orglett.7b00704.
Zhao, Q., Tognetti, V., Joubert, L., Besset, T., Pannecoucke, X., Bouillon, J. P., & Poisson, T. (2017). Palladium-Catalyzed Synthesis of 3-Trifluoromethyl-Substituted 1,3-Butadienes by Means of Directed C-H Bond Functionalization. Organic letters, 19(8), 2106-2109. https://doi.org/10.1021/acs.orglett.7b00704
Zhao, Qun, et al. "Palladium-Catalyzed Synthesis of 3-Trifluoromethyl-Substituted 1,3-Butadienes by Means of Directed C-H Bond Functionalization." Organic letters vol. 19,8 (2017): 2106-2109. doi: https://doi.org/10.1021/acs.orglett.7b00704
Zhao Q, Tognetti V, Joubert L, Besset T, Pannecoucke X, Bouillon JP, Poisson T. Palladium-Catalyzed Synthesis of 3-Trifluoromethyl-Substituted 1,3-Butadienes by Means of Directed C-H Bond Functionalization. Org Lett. 2017 Apr 21;19(8):2106-2109. doi: 10.1021/acs.orglett.7b00704. Epub 2017 Apr 05. PMID: 28378584.
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Org Lett. 2017 Apr 21;19(8):2106-2109. doi: 10.1021/acs.orglett.7b00704. Epub 2017 Apr 05.

Palladium-Catalyzed Synthesis of 3-Trifluoromethyl-Substituted 1,3-Butadienes by Means of Directed C-H Bond Functionalization.

Organic letters

Qun Zhao, Vincent Tognetti, Laurent Joubert, Tatiana Besset, Xavier Pannecoucke, Jean-Philippe Bouillon, Thomas Poisson

Affiliations

  1. Normandie Université, INSA Rouen , UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France.

PMID: 28378584 DOI: 10.1021/acs.orglett.7b00704

Abstract

A palladium-catalyzed C-H bond functionalization of acrylamides was developed to build up stereoselectively trifluoromethylated 1,3-butadienes. Using a tertiary amide as a directing group, olefins were selectively functionalized with 2-bromo-3,3,3-trifluoropropene to access these important fluorinated compounds. The methodology was extended to the construction of pentafluoroethyl-substituted 1,3-dienes. Mechanistic studies supported by density functional theory calculations suggested a redox neutral mechanism for this transformation.

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