1,6-Enyne Cyclizations Catalyzed by N-Heterocyclic Carbene Supported Gold Complexes: Deconvoluting Sterics and Electronics

被引：25
|
作者：
Arumugam, Kuppuswamy [1 ,2 ]
Varghese, Bibin [1 ]
Brantley, Johnathan N. [1 ]
Konda, Sai S. M. [1 ]
Lynch, Vincent M. [1 ]
Bielawski, Christopher W. [1 ]
机构：
[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA
[2] St Bonaventure Univ, Dept Chem, St Bonaventure, NY 14778 USA
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 03期
基金：
美国国家科学基金会;
关键词：
N-heterocyclic carbenes; Gold; Isomerization; Enynes; Steric hindrance; INTERMOLECULAR ADDITION; EFFICIENT; PLATINUM; LIGANDS; CYCLOISOMERIZATIONS; HYDROXYCYCLIZATION; ALKOXYCYCLIZATION; HYDROAMINATION; HYDROARYLATION; REARRANGEMENT;
D O I：
10.1002/ejoc.201301137
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of N-heterocyclic carbene (NHC) supported gold(I) complexes were synthesized, characterized in solution as well as in the solid state, and examined as precatalysts for 1,6-enyne cycloisomerization reactions. The product mixtures obtained for a variety of 1,6-enyne isomerizations were governed primarily by the electronic properties of the aforementioned precatalysts. In particular, precatalysts containing electronic-rich NHC ligands showed increased selectivity for bicyclic products, whereas analogous precatalysts supported by electron-deficient NHCs preferentially afforded olefinic products.
引用
收藏
页码：493 / 497
页数：5
相关论文
共 50 条
  • [31] Di(N-heterocyclic carbene) gold(III) imidate complexes obtained by oxidative addition of N-halosuccinimides
    Baron, Marco
    Dalla Tiezza, Marco
    Carlotto, Alice
    Tubaro, Cristina
    Graiff, Claudia
    Orian, Laura
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 866 : 144 - 152
  • [32] N-heterocyclic carbene supported Au(I) and Au(III) complexes: a comparison of cytotoxicities
    Dinda, Joydev
    Samanta, Tapastaru
    Nandy, Abhishek
    Das Saha, Krishna
    Seth, Saikat Kumar
    Chattopadhyay, Shymal Kumar
    Bielawskie, Christopher W.
    NEW JOURNAL OF CHEMISTRY, 2014, 38 (03) : 1218 - 1224
  • [33] Recent Developments on N-Heterocyclic Carbene Supported Zinc Complexes: Synthesis and Use in Catalysis
    Dagorne, Samuel
    SYNTHESIS-STUTTGART, 2018, 50 (18): : 3662 - 3670
  • [34] Cyclopropenation of internal alkynylsilanes and diazoacetates catalyzed by copper(I) N-heterocyclic carbene complexes
    Thomas, Thomas J.
    Merritt, Benjamin A.
    Lemma, Betsegaw E.
    Mckoy, Adina M.
    Tri Nguyen
    Swenson, Andrew K.
    Mills, Jeffrey L.
    Coleman, Michael G.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (05) : 1742 - 1747
  • [35] Synthesis and Biological Activity of Gold(I) N-Heterocyclic Carbene Complexes with Long Aliphatic Side Chains
    Arcau, Julia
    Andermark, Vincent
    Rodrigues, Mafalda
    Giannicchi, Ilaria
    Perez-Garcia, Lluisa
    Ott, Ingo
    Rodriguez, Laura
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2014, (35) : 6117 - 6125
  • [36] Gold-Catalyzed Intermolecular Oxidative Diyne Cyclizations via 1,6-Carbene Transfer
    Wang, Qian
    Rudolph, Matthias
    Rominger, Frank
    Hashmi, A. Stephen K.
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (04) : 755 - 759
  • [37] Synthesis and anticancer properties of gold(I) and silver(I) N-heterocyclic carbene complexes
    Siciliano, Tammy J.
    Deblock, Michael C.
    Hindi, Khadijah M.
    Durmus, Semih
    Panzner, Matthew J.
    Tessier, Claire A.
    Youngs, Wiley J.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (05) : 1066 - 1071
  • [38] Synthesis and antitumor activity of gold(I) N-heterocyclic carbene with dithiocarbamate and alkynyl complexes
    Chen, Qiu Mei
    Zeng, Yanyan
    Zhang, Ming Rui
    Jin, Lingyu
    Zhou, Ping
    Wu, Xiang Hua
    Ren, Wen Xiu
    INORGANICA CHIMICA ACTA, 2024, 568
  • [39] Anticancer Gold N-Heterocyclic Carbene Complexes: A Comparative in vitro and ex vivo Study
    Estrada-Ortiz, Natalia
    Guarra, Federica
    de Graaf, Inge A. M.
    Marchetti, Lorella
    de Jager, Marina H.
    Groothuis, Geny M. M.
    Gabbiani, Chiara
    Casini, Angela
    CHEMMEDCHEM, 2017, 12 (17) : 1429 - 1435
  • [40] Probing Conformational Variation in Luminescent Dinuclear Gold(I) N-Heterocyclic Carbene Complexes
    Pell, Thomas P.
    Stringer, Bradley D.
    Tubaro, Cristina
    Hogan, Conor F.
    Wilson, David J. D.
    Barnard, Peter J.
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2017, (30) : 3661 - 3674
12345