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

共 50 条

[41] Dinuclear silver(I)-N-heterocyclic carbene complexes: Synthesis, characterization and larvicidal activity of bis-imidazolium dinuclear silver (I)-N-heterocyclic carbene complexes
Selvarajoo, Puvana D.
Haque, Rosenani A.
Haziz, Umie F. M.
Avicor, Silas W.
Wajidi, Mustafa F. F.
Razali, Mohd R.
JOURNAL OF INORGANIC BIOCHEMISTRY, 2017, 175 : 232 - 238
[42] Synthetic routes to [Au(NHC)(OH)] (NHC = N-heterocyclic carbene) complexes
Gomez-Suarez, Adrian
Ramon, Ruben S.
Slawin, Alexandra M. Z.
Nolan, Steven P.
DALTON TRANSACTIONS, 2012, 41 (18) : 5461 - 5463
[43] Amine-tethered N-heterocyclic carbene complexes of rhodium(I)
Jong, Howard
Patrick, Brian O.
Fryzuk, Michael D.
CANADIAN JOURNAL OF CHEMISTRY, 2008, 86 (08) : 803 - 810
[44] Studies of Ligand Exchange in N-Heterocyclic Carbene Silver(I) Complexes
Su, Haw-Lih
Perez, Lisa M.
Lee, Sheng-Jui
Reibenspies, Joseph H.
Bazzi, Hassan S.
Bergbreiter, David E.
ORGANOMETALLICS, 2012, 31 (10) : 4063 - 4071
[45] Synthesis and structures of cyclopentadienyl N-heterocyclic carbene copper(I) complexes
Ren, Hongping
Zhao, Xi
Xu, Shansheng
Song, Haibin
Wang, Baiquan
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (19) : 4109 - 4113
[46] Rhodium(i) N-heterocyclic carbene complexes: synthesis and cytotoxic properties
Slimani, Ichraf
Sahin-Bolukbasi, Serap
Ulu, Mustafa
Evren, Enes
Gurbuz, Nevin
Ozdemir, Ilknur
Hamdi, Naceur
Ozdemir, Ismail
NEW JOURNAL OF CHEMISTRY, 2021, 45 (11) : 5176 - 5183
[47] Ligand exchange studies of N-heterocyclic carbene Ag(I) complexes
Su, Haw-Lih
Lee, Sheng-Jui
Bazzi, Hassan S.
Bergbreiter, David E.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
[48] Properties and prospects for rhenium(i) tricarbonyl N-heterocyclic carbene complexes
Simpson, Peter V.
Falasca, Marco
Massi, Massimiliano
CHEMICAL COMMUNICATIONS, 2018, 54 (88) : 12429 - 12438
[49] Ag(I) N-heterocyclic carbene complexes: Synthesis, structure, and application
Garrison, JC
Youngs, WJ
CHEMICAL REVIEWS, 2005, 105 (11) : 3978 - 4008
[50] New N-heterocyclic carbene mercury(II) and silver(I) complexes
Liu, Qing-Xiang
Yin, Li-Na
Wu, Xiu-Mei
Feng, Jin-Cheng
Guo, Jian-Hua
Song, Hai-Bin
POLYHEDRON, 2008, 27 (01) : 87 - 94

← 1 2 3 4 5 →