Display options
Cite
Rout L, Parida BB, Florent JC, et al. Metal-Free Activation of a C(sp)-H Bond of Aryl Acetylenes. Chemistry. 2016;22(42):14812-14815doi: 10.1002/chem.201603003.
Rout, L., Parida, B. B., Florent, J. C., Johannes, L., Choudhury, S. K., Phaomei, G., Scanlon, J., & Bertounesque, E. (2016). Metal-Free Activation of a C(sp)-H Bond of Aryl Acetylenes. Chemistry (Weinheim an der Bergstrasse, Germany), 22(42), 14812-14815. https://doi.org/10.1002/chem.201603003
Rout, Laxmidhar, et al. "Metal-Free Activation of a C(sp)-H Bond of Aryl Acetylenes." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,42 (2016): 14812-14815. doi: https://doi.org/10.1002/chem.201603003
Rout L, Parida BB, Florent JC, Johannes L, Choudhury SK, Phaomei G, Scanlon J, Bertounesque E. Metal-Free Activation of a C(sp)-H Bond of Aryl Acetylenes. Chemistry. 2016 Oct 10;22(42):14812-14815. doi: 10.1002/chem.201603003. Epub 2016 Aug 30. PMID: 27504988.
Copy Download .nbib Format: NLM
Share it on

Chemistry. 2016 Oct 10;22(42):14812-14815. doi: 10.1002/chem.201603003. Epub 2016 Aug 30.

Metal-Free Activation of a C(sp)-H Bond of Aryl Acetylenes.

Chemistry (Weinheim an der Bergstrasse, Germany)

Laxmidhar Rout, Bibhuti Bhusan Parida, Jean-Claude Florent, Ludger Johannes, Santosh Kumar Choudhury, Ganngam Phaomei, Joe Scanlon, Emmanuel Bertounesque

Affiliations

  1. Department of Chemistry, Berhampur University, Bhanjabihar, Odisha, 760007, India. [email protected], [email protected].
  2. Chemical Biology of Membranes and Therapeutic Delivery, Institut de Curie, Centre de Recherche U1143 INSERM, UMR 3666 CNRS, 26 rue d'Ulm, 75248, Paris, Cedex 05, France. [email protected], [email protected].
  3. Chemical Biology of Membranes and Therapeutic Delivery, Institut de Curie, Centre de Recherche U1143 INSERM, UMR 3666 CNRS, 26 rue d'Ulm, 75248, Paris, Cedex 05, France. [email protected].
  4. Chemical Biology of Membranes and Therapeutic Delivery, Institut de Curie, Centre de Recherche U1143 INSERM, UMR 3666 CNRS, 26 rue d'Ulm, 75248, Paris, Cedex 05, France.
  5. Department of Chemistry, Berhampur University, Bhanjabihar, Odisha, 760007, India.
  6. Department of Chemistry, Rippon College, 316 Farr Hall, Ripon, WI, USA.
  7. Chemical Biology of Membranes and Therapeutic Delivery, Institut de Curie, Centre de Recherche U1143 INSERM, UMR 3666 CNRS, 26 rue d'Ulm, 75248, Paris, Cedex 05, France. [email protected].

PMID: 27504988 DOI: 10.1002/chem.201603003

Abstract

C(sp)-H Bond activation of acetylene molecule still remains a challenge for synthetic organic chemists. In practice, acetylenes are activated by strong bases and metals. The first example for activating acetylenic protons under base and metal-free conditions is reported here. It involves a general method for synthesizing propargylic derivatives of cotarnine. An array of tetrahydroisoquinolines alkaloids was synthesized by C(sp)-H bond activation of aromatic acetylenes with cotarnine at room temperature. A DFT-based mechanism is proposed for the reaction.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: alkaloid; cotarnine; density functional calculations; isoquinoline; phenylacetylene

Publication Types