Copper-catalyzed dehydrogenative γ-C(sp3)-H amination of saturated ketones for synthesis of polysubstituted anilines

Rong Hu, Fa-Jie Chen, Xiaofeng Zhang, Min Zhang and Weiping Su ()
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Rong Hu: ShanghaiTech University
Fa-Jie Chen: Chinese Academy of Sciences
Xiaofeng Zhang: Chinese Academy of Sciences
Min Zhang: Chinese Academy of Sciences
Weiping Su: ShanghaiTech University

Nature Communications, 2019, vol. 10, issue 1, 1-10

Abstract: Abstract Metal-catalyzed β-C-H functionalization of saturated carbonyls via dehydrogenative desaturation proved to be a powerful tool for simplifying synthesis of valuable β-substituted carbonyls. Here, we report a copper-catalyzed dehydrogenative γ-C(sp3)-H amination of saturated ketones that initiates the three-component coupling of saturated ketones, amines and N-substituted maleimides to construct polysubstituted anilines. The protocol presented herein enables both linear and α-branched butanones to couple a wide spectrum of amines and various N-substituted maleimides to produce diverse tetra- or penta-substituted anilines in fair-to-excellent yields with good functional group tolerance. The mechanism studies support that this ketone dehydrogenative γ-C(sp3)-H amination was triggered by the ketone α,β-dehydrogenation desaturation that activates the adjacent γ-C(sp3)-H bond towards functionalization. This α,β-dehydrogenation desaturation-triggered cascade sequence opens up a new avenue to the remote C(sp3)-H functionalization of saturated ketones and has the potential to enable the rapid syntheses of complex compounds from simple starting materials.

Date: 2019
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DOI: 10.1038/s41467-019-11624-9

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