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. 2018 Sep 18;9(46):8711-8715.
doi: 10.1039/c8sc03480j. eCollection 2018 Dec 14.

Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes

Qiao Chen  1 , Tingshun Zhu  1 , Pankaj Kumar Majhi  1 , Chengli Mou  2 , Huifang Chai  2 , Jingjie Zhang  2 , Shitian Zhuo  1 , Yonggui Robin Chi  1
Affiliations

Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes

Qiao Chen et al. Chem Sci. .

Abstract

Di(hetero)arylmethane is a unique structural motif for natural and synthetic functional molecules. To date, it remains challenging to functionalize the diaryl methyl sp3 carbon-hydrogen bond directly in an enantioselective manner. This is likely due to the relatively inert nature of the carbon-hydrogen bond and the difficult enantiofacial discrimination of two sterically similar aryl substituents. Here we disclose an N-heterocyclic carbene-catalyzed direct oxidative coupling of enals and di(hetero)arylmethanes. Our method allows for highly enantioselective transformation of diaryl methanes and quick access to benzimidazole fused lactams.

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Figures

Fig. 1
Fig. 1. Diarylmethyl compounds and their enantioselective synthesis.
Scheme 1
Scheme 1. Control test.
Scheme 2
Scheme 2. Possible reaction pathways.
Scheme 3
Scheme 3. Product Transformation.
See this image and copyright information in PMC

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