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Lewis Base-Boryl Radicals Enabled the Desulfurizative Reduction and Annulation of Thioamides
You-Jie Yu1, Feng-Lian Zhang1, Jie Cheng1
1Hefei 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.
Abstract:
A new protocol for radical transformations of thioamides promoted by Lewis base-boryl radicals is reported. The desulfurizative reduction to access organic amines was enabled utilizing 4-dimethylaminopyridine-BH3 as the boryl radical precursor and PhSH as the polarity reversal catalyst. Alternatively, the chain process for unsaturated thioamides was switched to an annulation reaction using N-heterocyclic carbene-BH3 as the boryl radical precursor and sterically bulky Ph3CSH as the catalyst, allowing for the construction of N-heterocyclic and carbocyclic skeletons.
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