Multifunctional 1,3-diphenylguanidine for the carboxylative cyclization of homopropargyl amines with CO2 under ambient temperature and pressure

Xiao-Tong Gao; Shi-Liang Xie; Feng Zhou; Hai-Hong Wu; Jian Zhou

doi:10.1039/C9CC07671A

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Multifunctional 1,3-diphenylguanidine for the carboxylative cyclization of homopropargyl amines with CO₂ under ambient temperature and pressure†

Xiao-Tong Gao,^a Shi-Liang Xie,^a Feng Zhou,

*^ab Hai-Hong Wu

*^a and Jian Zhou

*^abc

Author affiliations

* Corresponding authors

^a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University, Shanghai, China
E-mail: fzhou@chem.ecnu.edu.cn, hhwu@chem.ecnu.edu.cn

^b Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, China
E-mail: jzhou@chem.ecnu.edu.cn

^c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, China

Abstract

Herein, we report that 1,3-diphenylguanidine (DPG) could be utilized for the carboxylative cyclization of homopropargyl amines with CO₂ under ambient temperature and pressure, in combination with AgSbF₆, 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.

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Article information

DOI: https://doi.org/10.1039/C9CC07671A
Article type: Communication
Submitted: 30 Sep 2019
Accepted: 21 Oct 2019
First published: 21 Oct 2019

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Chem. Commun., 2019,55, 14303-14306

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Multifunctional 1,3-diphenylguanidine for the carboxylative cyclization of homopropargyl amines with CO₂ under ambient temperature and pressure

X. Gao, S. Xie, F. Zhou, H. Wu and J. Zhou, Chem. Commun., 2019, 55, 14303 DOI: 10.1039/C9CC07671A

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