Lewis Base-Boryl Radicals Enabled the Desulfurizative Reduction and Annulation of Thioamides

You-Jie Yu, Feng-Lian Zhang, Jie Cheng, Jing-Hao Hei, Wei-Ting Deng and Yi-Feng Wang*

*Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China, Email: yfwangzjustc.edu.cn

Y.-J. Yu, F.-L. Zhang, J. Cheng, J.-H. Hei, W.-T. Deng, Y.-F. Wang, Org. Lett., 2018, 20, 24-27.

DOI: 10.1021/acs.orglett.7b03201

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Abstract

4-Dimethylaminopyridine-BH₃ as the boryl radical precursor promotes a desulfurizative reduction to access organic amines in the presence of PhSH as the polarity reversal catalyst. Alternatively a N-heterocyclic carbene-BH₃ as the boryl radical precursor and sterically bulky Ph₃CSH as catalyst can be used for annulation of unsaturated thioamides allowing for the construction of N-heterocyclic and carbocyclic skeletons.

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proposed mechanism

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Key Words

desulfurization, 4-dimethylaminopyridine borane

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ID: J54-Y2018