Lanthanide/B(C₆F₅)₃-Promoted Hydroboration Reduction of Indoles and Quinolines with Pinacolborane

Jianping Zhang, Ziyan Chen, Mingxin Chen, Qi Zhou, Rongrong Zhou, Wenli Wang, Yinlin Shao*, Fangjun Zhang*

*Wenzhou University, Wenzhou 325035; Wenzhou Medical University, Wenzhou 325035, China, Email: shaoylwzu.edu.cn, zhangfjwmu.edu.cn

J. Zhang, Z. Chen, M. Chen, Q. Zhou, R. Zhou, W. Wang, Y. Shao, F. Zhang, J. Org. Chem., 2024, 89, 887-897.

DOI: 10.1021/acs.joc.3c01767

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Abstract

A lanthanide/B(C₆F₅)₃-promoted hydroboration reduction of indoles and quinolines with pinacolborane (HBpin) provides a range of nitrogen-containing compounds in good yields. Large-scale synthesis and further transformations to bioactive compounds indicate that the method has potential practical applications.

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proposed mechanism

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Key Words

indolines, tetrahydroquinolines, pinacolborane

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ID: J42-Y2024