Pd(0)-Catalyzed Asymmetric Carbohalogenation: H-Bonding-Driven C(sp₃)-Halogen Reductive Elimination under Mild Conditions

Xin Chen, Jixiao Zhao, Ming Dong, Ninglei Yang, Jiaoyang Wang, Yueqi Zhang, Kun Liu* and Xiaofeng Tong*

*Tianjin Normal University, 393 Binshui West Road, Tianjin 300387; Changzhou University, 1 Gehu Road, Changzhou 213164, China, Email: hxxyliuktjnu.edu.cn, txfcczu.edu.cn

X. Chen, J. Zhao, M. Dong, N. Yang, J. Wang, Y. Zhang, K. Liu, X. Tong, J. Am. Chem. Soc., 2021, 143, 1924-1931.

DOI: 10.1021/jacs.0c10797

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Abstract

[Et₃NH]⁺[BF₄]^- as an H-bond donor in a toluene/water/(CH₂OH)₂ biphasic system efficiently promotes a transition-metal catalyzed carbon-halogen reductive elimination at low temperature. This enables a series of Pd(0)-catalyzed carbohalogenation reactions, including an unprecedented asymmetric carbobromination in the presence of readily available ligands.

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Key Words

1,2,3,6-Tetrahydropyridines

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ID: J48-Y2021