title: Metal-Free Activation of a C(sp)-H Bond of Aryl Acetylenes.
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.
authors: Department of Chemistry, Berhampur University, Bhanjabihar, Odisha, 760007, India. routlaxmi@gmail.com, ldr.chem@buodisha.edu.in.|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. routlaxmi@gmail.com, ldr.chem@buodisha.edu.in.
authors: Laxmidhar
authors: http://orcid.org/0000-0002-1432-2559
authors: L
authors: Rout
authors: 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. bbparida80@gmail.com.
authors: Bibhuti Bhusan
authors: BB
authors: Parida
authors: 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.
authors: Jean-Claude
authors: JC
authors: Florent
authors: 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.
authors: Ludger
authors: L
authors: Johannes
authors: Department of Chemistry, Berhampur University, Bhanjabihar, Odisha, 760007, India.
authors: Santosh Kumar
authors: SK
authors: Choudhury
authors: Department of Chemistry, Berhampur University, Bhanjabihar, Odisha, 760007, India.
authors: Ganngam
authors: G
authors: Phaomei
authors: Department of Chemistry, Rippon College, 316 Farr Hall, Ripon, WI, USA.
authors: Joe
authors: J
authors: Scanlon
authors: 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. Emmanuel.Bertounesque@curie.fr.
authors: Emmanuel
authors: E
authors: Bertounesque
keywords: alkaloid; cotarnine; density functional calculations; isoquinoline; phenylacetylene