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
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