Aryl-BIAN-ligated silver(I) trifluoromethoxide complex

被引：60

作者：

Chen, Shouxiong ^{[1
]}

Huang, Yangjie ^{[1
]}

Fang, Xin ^{[1
]}

Li, Haohong ^{[1
]}

Zhang, Zhongxing ^{[2
]}

Hor, T. S. Andy ^{[2
,3
]}

Weng, Zhiqiang ^{[1
]}

机构：

[1] Fuzhou Univ, Coll Chem, State Key Lab Photocatalysis Energy & Environm, Fuzhou 350108, Peoples R China

[2] ASTAR, Inst Mat Res & Engn, Singapore 117602, Singapore

[3] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

来源：

DALTON TRANSACTIONS | 2015年 / 44卷 / 45期

基金：

高等学校博士学科点专项科研基金; 中国国家自然科学基金;

关键词：

ALPHA-FLUORINATED ETHERS; OXIDATIVE DESULFURIZATION-FLUORINATION; BIDENTATE NITROGEN LIGANDS; ORGANOMETALLIC CHEMISTRY; SUBSTITUENT CONSTANTS; HOMOGENEOUS CATALYSIS; COPPER; ALKYNES; TRIFLUOROMETHYLSELENOLATION; DERIVATIVES;

D O I：

10.1039/c5dt02078f

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A reaction of acetonitrile-solvated AgOCF3 with 1 equiv. of Aryl-BIAN ligand in THF at room-temperature afforded the silver(I) complex (Aryl-BIAN)AgOCF3 (1) in 75% yield. The crystal structure of this silver(I) trifluoromethoxide was determined by single-crystal X-ray crystallography. The molecular structure of 1 shows the metal centre bound to one molecule of BIAN, one trifluoromethoxide and one THF solvate, resulting in a distorted tetrahedral silver. Density functional theory (DFT) calculations and the natural bond orbital (NBO) analysis were conducted to give insights into the electronic structure of 1 and the bonding characters of the OCF3 group. The reactivity of 1 towards trifluoromethoxylation of organic halides was also examined; a reaction with benzyl bromides gave the desired products of benzyl trifluoromethyl ethers in good to excellent yields.

引用

页码：19682 / 19686

页数：5

共 56 条

[21] Silver-Mediated Trifluoromethoxylation of Aryl Stannanes and Arylboronic Acids [J].

Huang, Chenghong ;

Liang, Theresa ;

Harada, Shinji ;

Lee, Eunsung ;

Ritter, Tobias .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (34) :13308-13310

[22] Well-Defined Copper(I) Fluoroalkoxide Complexes for Trifluoroethoxylation of Aryl and Heteroaryl Bromides [J].

Huang, Ronglu ;

Huang, Yangjie ;

Lin, Xiaoxi ;

Rong, Mingguang ;

Weng, Zhiqiang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (19) :5736-5739

[23] Selective aromatic carbon-oxygen bond cleavage of trifluoromethoxyarenes: a trifluoromethoxy group as a convertible directing group [J].

Iijima, Akinori ;

Amii, Hideki .

TETRAHEDRON LETTERS, 2008, 49 (41) :6013-6015

[24] Oxidative desulfurization-fluorination of alkanol xanthates. Control of the reaction pathway to fluorination or trifluoromethoxylation [J].

Kanie, K ;

Tanaka, Y ;

Shimizu, M ;

Kuroboshi, M ;

Hiyama, T .

CHEMICAL COMMUNICATIONS, 1997, (03) :309-310

[25]

Kirsch P., 2004, MODERN FLUOROORGANIC

[26] Zinc-Mediated Formation of Trifluoromethyl Ethers from Alcohols and Hypervalent Iodine Trifluoromethylation Reagents [J].

Koller, Raffael ;

Stanek, Kyrill ;

Stolz, Daniel ;

Aardoom, Raphael ;

Niedermann, Katrin ;

Togni, Antonio .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (24) :4332-4336

[27] Versatile application of trifluoromethyl triflate [J].

Kolomeitsev, Alexander A. ;

Vorobyev, Mikhail ;

Gillandt, Hartmut .

TETRAHEDRON LETTERS, 2008, 49 (03) :449-454

[28] OXIDATIVE DESULFURIZATION-FLUORINATION OF XANTHATES - A CONVENIENT SYNTHESIS OF TRIFLUOROMETHYL ETHERS AND DIFLUORO(METHYLTHIO)METHYL ETHERS [J].

KUROBOSHI, M ;

SUZUKI, K ;

HIYAMA, T .

TETRAHEDRON LETTERS, 1992, 33 (29) :4173-4176

[29] α-fluorinated ethers, thioethers, and amines:: Anomerically biased species [J].

Leroux, F ;

Jeschke, P ;

Schlosser, M .

CHEMICAL REVIEWS, 2005, 105 (03) :827-856

[30] Trifluoromethyl ethers - synthesis and properties of an unusual substituent [J].

Leroux, Frederic R. ;

Manteau, Baptiste ;

Vors, Jean-Pierre ;

Pazenok, Sergiy .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2008, 4

← 1 2 3 4 5 6 →