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. 2018 Sep 10;57(37):12071-12075.
doi: 10.1002/anie.201806287. Epub 2018 Aug 20.

Manganese-Catalyzed Redox-Neutral C-H Olefination of Ketones with Unactivated Alkenes

Yuanyuan Hu  1   2 , Bingwei Zhou  1   2 , Hui Chen  3 , Congyang Wang  1   2
Affiliations

Manganese-Catalyzed Redox-Neutral C-H Olefination of Ketones with Unactivated Alkenes

Yuanyuan Hu et al. Angew Chem Int Ed Engl. .

Abstract

Since 1987, stoichiometric cyclomanganation of ketones and subsequent reactions with olefins in the presence of either palladium salts or trimethylamine N-oxide (Me3 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.

Keywords: C−H activation; alkenes; ketones; manganese; olefination.

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