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Manganese‐Catalyzed Redox‐Neutral C−H Olefination of Ketones with Unactivated Alkenes
Author(s) -
Hu Yuanyuan,
Zhou Bingwei,
Chen Hui,
Wang Congyang
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201806287
Subject(s) - metalation , chemistry , catalysis , reactivity (psychology) , deprotonation , manganese , redox , stoichiometry , medicinal chemistry , reaction mechanism , photochemistry , organic chemistry , ion , medicine , alternative medicine , pathology
Since 1987, stoichiometric cyclomanganation of ketones and subsequent reactions with olefins in the presence of either palladium salts or trimethylamine N ‐oxide (Me 3 N + O − ) have been reported, but the catalytic versions remain untouched so far. Herein, the first manganese‐catalyzed redox‐neutral C−H olefination of ketones with unactivated alkenes is described, and shows a distinct reactivity with its parent stoichimetric reactions. Remarkably, mechanistic experiments and DFT calculations uncovers a unique concerted bis‐metalation deprotonation (CBMD) mechanism of the Mn‐Zn‐enabled C−H bond activation.