The mechanism of carboxylative cyclization of propargylamine by N-heterocyclic carbene complexes of Au(I)

被引：1
作者：
Davis, Jack, V [1 ]
Gamage, Mohan M. [1 ]
Guio, Oswaldo [1 ]
Bayrakdar, Tahani A. C. A. [2 ,3 ]
Nolan, Steven P. [2 ,3 ]
Temprado, Manuel [4 ,5 ]
Captain, Burjor [1 ]
Hoff, Carl D. [1 ]
机构：
[1] Univ Miami, Dept Chem, Coral Gables, FL 33146 USA
[2] Univ Ghent, Dept Chem, Krijgslaan 281,S-3, B-9000 Ghent, Belgium
[3] Univ Ghent, Ctr Sustainable Chem, Krijgslaan 281,S-3, B-9000 Ghent, Belgium
[4] Univ Alcala, Dept Quim Analit Quim Fis & Ingn Quim, Campus Univ, Madrid 28805, Spain
[5] Univ Alcala, Inst Invest Quim Andres M del Rio IQAR, Campus Univ, Madrid 28805, Spain
来源：
JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2021年 / 934卷
关键词：
CARBON-DIOXIDE; NHC; CATALYSTS; BEARING; BR; CL;
D O I：
10.1016/j.jorganchem.2020.121583
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The complex [Au(IPr)(2-oxazolidinone)] (1 = IKa) was prepared from reaction of [Au(IPr)Cl] (2), K2CO3, and propargyl amine (PPA). Kinetic studies have been performed for acid cleavage of 1 to yield the oxazolidinone product and an [Au(IPr)(X)] adduct. The fastest rates of cleavage were found to occur for the hydrogen chloride salt of PPA (PPA-HCl) and for the CO2 adduct of PPA, PPA-CO2 = the carbamic acid (CA). This transformation was studied as a function of [CA], pressure of CO2 as well as temperature. Detailed computational studies support the formation of a key intermediate and are also in agreement with a rapid carbonylation/decarbonylation reaction. The computed reactions mechanisms for addition of PPAHCl and CA are also presented as well as the crystal structure of 1. (C) 2020 Elsevier B.V. All rights reserved.
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页数：12
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