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Metal‐Free Activation of a C(sp)−H Bond of Aryl Acetylenes
Author(s) -
Rout Laxmidhar,
Parida Bibhuti Bhusan,
Florent JeanClaude,
Johannes Ludger,
Choudhury Santosh Kumar,
Phaomei Ganngam,
Scanlon Joe,
Bertounesque Emmanuel
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603003
Subject(s) - aryl , metal , chemistry , stereochemistry , organic chemistry , alkyl
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.