Ruthenium catalyzed amination cyclization of 1,2,4-butanetriol with primary amines: A borrowing hydrogen strategy for 3-pyrrolidinol synthesis

Highly valuable N-aryl 3-pyrrolidinols are prepared from cheap primary aryl amines and 1,2,4-butanetriol via a ruthenium catalyzed amination cyclization reaction. The two fold hydrogen autotransfer or borrowing hydrogen process of N-alkylation is extremely clean, efficient and compatible with Cl/Br...

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Bibliographic Details
Published in:Chinese chemical letters 2020-01, Vol.31 (1), p.103-106
Main Authors: Xu, Qing-Song, Li, Chen, Xu, Yong, Xu, Defeng, Shen, Mei-Hua, Xu, Hua-Dong
Format: Article
Language:English
Subjects:
1,2,4-Butanetriol
3-Pyrrolidinol
[Ru(p-cymene)Cl2]2
Amination cyclization
Borrowing hydrogen
Hydrogen autotransfer
N-Alkylation
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Summary:Highly valuable N-aryl 3-pyrrolidinols are prepared from cheap primary aryl amines and 1,2,4-butanetriol via a ruthenium catalyzed amination cyclization reaction. The two fold hydrogen autotransfer or borrowing hydrogen process of N-alkylation is extremely clean, efficient and compatible with Cl/Br substituted anilines. [Display omitted] A ruthenium based catalytic system ([Ru(p-cymene)Cl2]2/XantPhos with substoichiometric Cs2CO3) has been established to effectively achieve the first direct amination cyclization of 1,2,4-butanetriol with primary aromatic amines. The product of this sustainable hydrogen autotransfer process is valuable N-aryl-3-pyrrolidinol.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2019.05.027