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.

引用

页数：12

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