Homoleptic Bis(trimethylsilyl)amides of Yttrium Complexes Catalyzed Hydroboration Reduction of Amides to Amines

Homoleptic lanthanide complex Y­[N­(TMS)2]3 is an efficient homogeneous catalyst for the hydroboration reduction of secondary amides and tertiary amides to corresponding amines. A series of amides containing different functional groups such as cyano, nitro, and vinyl groups were found to be well-tol...

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Bibliographic Details
Published in:Organic letters 2020-02, Vol.22 (4), p.1306-1310
Main Authors: Ye, Pengqing, Shao, Yinlin, Ye, Xuanzeng, Zhang, Fangjun, Li, Renhao, Sun, Jiani, Xu, Beihang, Chen, Jiuxi
Format: Article
Language:English
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Summary:Homoleptic lanthanide complex Y­[N­(TMS)2]3 is an efficient homogeneous catalyst for the hydroboration reduction of secondary amides and tertiary amides to corresponding amines. A series of amides containing different functional groups such as cyano, nitro, and vinyl groups were found to be well-tolerated. This transformation has also been nicely applied to the synthesis of indoles and piribedil. Detailed isotopic labeling experiments, control experiments, and kinetic studies provided cumulative evidence to elucidate the reaction mechanism.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b04606