Multifunctional 1,3-diphenylguanidine for the carboxylative cyclization of homopropargyl amines with CO under ambient temperature and pressure

Herein, we report that 1,3-diphenylguanidine (DPG) could be utilized for the carboxylative cyclization of homopropargyl amines with CO 2 under ambient temperature and pressure, in combination with AgSbF 6 , which enabled the synthesis of both chiral and achiral 2-oxazinones efficiently. A mechanisti...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-11, Vol.55 (95), p.1433-1436
Main Authors: Gao, Xiao-Tong, Xie, Shi-Liang, Zhou, Feng, Wu, Hai-Hong, Zhou, Jian
Format: Article
Language:English
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Summary:Herein, we report that 1,3-diphenylguanidine (DPG) could be utilized for the carboxylative cyclization of homopropargyl amines with CO 2 under ambient temperature and pressure, in combination with AgSbF 6 , which enabled the synthesis of both chiral and achiral 2-oxazinones efficiently. A mechanistic study revealed that the multi-functionality of DPG is critical to the success of the reaction. The highly efficient multifunctional DPG promoted carboxylative cyclization of homopropargyl amines with CO 2 to form six-membered 2-oxazinones was developed under ambient temperature and pressure.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc07671a