Palladium catalyzed ortho-C(sp2)–H activation/cyclization of aryl amines assisted by imine and vinylacetic acid

Xiangwen Tan, Yaru Jing, Jiahao Wu, Jiatian Li, Zhenjie Yang, Wanqing Wu, Zhuofeng Ke () and Huanfeng Jiang ()
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Xiangwen Tan: South China University of Technology
Yaru Jing: Sun Yat-sen University
Jiahao Wu: South China University of Technology
Jiatian Li: South China University of Technology
Zhenjie Yang: Sun Yat-sen University
Wanqing Wu: South China University of Technology
Zhuofeng Ke: Sun Yat-sen University
Huanfeng Jiang: South China University of Technology

Nature Communications, 2024, vol. 15, issue 1, 1-12

Abstract: Abstract Palladium-catalyzed directed C − H functionalization/cyclization is an effective approach for synthesizing nitrogen heterocycles. Imine, known for its ease of installation/removal, has been extensively used in the C–H activation of aldehydes, ketones, and alkylamines. Nevertheless, it has been rarely explored in the C(sp2)–H activation of aryl amines because of the generation of a strained four-membered palladacycle. Herein, an imine directed palladium catalyzed C(sp2)–H functionalization of aryl amines assisted by vinylacetic acid is established, providing access to a variety of γ-lactone fused tetrahydroquinolines under mild reaction conditions. The methodology demonstrates broad substrate scope and good functional group tolerance, representing notable advancement in organic synthesis. Mechanistic experiments are performed to clarify how the C(sp2)–H activation occurs, indicating the crucial role of vinylacetic acid. DFT calculations supports the observations, elucidating the strained four-membered ring C–H activation barrier is overcome via coordination and hydrogen bond interaction of vinylacetic acid.

Date: 2024
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DOI: 10.1038/s41467-024-54018-2

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