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Ligand‐Promoted Non‐Directed C−H Cyanation of Arenes
Author(s) -
Liu LuoYan,
Yeung KapSun,
Yu JinQuan
Publication year - 2019
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.201805772
Subject(s) - cyanation , chemistry , reagent , limiting , combinatorial chemistry , ligand (biochemistry) , rate determining step , bond cleavage , kinetic isotope effect , stereochemistry , medicinal chemistry , organic chemistry , catalysis , deuterium , receptor , mechanical engineering , biochemistry , engineering , physics , quantum mechanics
This article reports the first example of a 2‐pyridone accelerated non‐directed C−H cyanation with an arene as the limiting reagent. This protocol is compatible with a broad scope of arenes, including advanced intermediates, drug molecules, and natural products. A kinetic isotope experiment ( k H / k D =4.40) indicates that the C−H bond cleavage is the rate‐limiting step. Also, the reaction is readily scalable, further showcasing the synthetic utility of this method.