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Metal‐Free Activation of a C(sp)−H Bond of Aryl Acetylenes |
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| Authors: | Prof. Laxmidhar Rout Dr. Bibhuti Bhusan Parida Dr. Jean‐Claude Florent Dr. Ludger Johannes Santosh Kumar Choudhury Dr. Ganngam Phaomei Prof. Joe Scanlon Dr. Emmanuel Bertounesque |
| Affiliation: | 1. Department of Chemistry, Berhampur University, Bhanjabihar, Odisha, India;2. Chemical Biology of Membranes and Therapeutic Delivery, Institut de Curie, Centre de Recherche U1143 INSERM, UMR 3666 CNRS, Paris, Cedex 05, France;3. Department of Chemistry, Rippon College, Ripon, WI, USA |
| 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. |
| Keywords: | alkaloid cotarnine density functional calculations isoquinoline phenylacetylene |