Active trifluoromethylating agents from well-defined copper(I)-CF3 complexes

被引：347

作者：

Dubinina, Galyna G. ^{[1
]}

Furutachi, Hideki ^{[2
]}

Vicic, David A. ^{[1
]}

机构：

[1] Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA

[2] Kanazawa Univ, Div Mat Sci, Grad Sch Nat Sci & Technol, Kanazawa, Ishikawa 9201192, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 27期

关键词：

D O I：

10.1021/ja802946s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first examples of isolable and structurally characterized Cu(I)-CF3 complexes are reported. N-Heterocyclic carbene (NHC)-supported copper tert-butoxide complexes reacted with Me3Si-CF3 to afford new (NHC)Cu-CF3 complexes whose structures were dependent on whether or not the C-4-C-5 positions of the five-membered NHC rings were saturated. In situ generated (Sl/Pr)Cu-CF3 cleanly transferred its trifluoromethyl group to a number of organic halides under mild conditions.

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页码：8600 / +

页数：3

相关论文

共 24 条

[1] Firms invent new strategies to deflect generic competition and stem growing safety concerns [J].

Ainsworth, Susan J. .

CHEMICAL & ENGINEERING NEWS, 2007, 85 (49) :17-+

[2] Regioselective C-H activation of lanthanide-bound N-heterocyclic carbenes [J].

Arnold, PL ;

Liddle, ST .

CHEMICAL COMMUNICATIONS, 2005, (45) :5638-5640

[3]

Banks R.E., 1994, ORGANOFLUORINE CHEM

[4] Sodium trifluoroacetate: an efficient precursor for the trifluoromethylation of aldehydes [J].

Chang, Y ;

Cai, C .

TETRAHEDRON LETTERS, 2005, 46 (18) :3161-3164

[5] A NOVEL TRIFLUOROMETHYLATION METHOD OF SATURATED ORGANIC HALIDES [J].

CHEN, QY ;

DUAN, JX .

TETRAHEDRON LETTERS, 1993, 34 (26) :4241-4244

[6] STUDIES ON FLUOROALKYLATION AND FLUOROALKOXYLATION .33. DIRECT TRIFLUOROMETHYLATION OF ARYL HALIDES WITH FLUOROSULPHONYLDIFLUOROMETHYL IODIDE IN THE PRESENCE OF COPPER - AN ELECTRON-TRANSFER INDUCED PROCESS [J].

CHEN, QY ;

WU, SW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (12) :2385-2387

[7]

Cottet F, 2002, EUR J ORG CHEM, V2002, P327

[8] Steric and electronic properties of N-heterocyclic carbenes (NHC):: A detailed study on their interaction with Ni(CO)4 [J].

Dorta, R ;

Stevens, ED ;

Scott, NM ;

Costabile, C ;

Cavallo, L ;

Hoff, CD ;

Nolan, SP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (08) :2485-2495

[9]

Filler R., 1993, ORGANOFLUORINE COMPO

[10] Ligand redox effects in the synthesis, electronic structure, and reactivity of an alkyl-alkyl cross-coupling catalyst [J].

Jones, Gavin D. ;

Martin, Jason L. ;

McFarland, Chris ;

Allen, Olivia R. ;

Hall, Ryan E. ;

Haley, Aireal D. ;

Brandon, R. Jacob ;

Konovalova, Tatyana ;

Desrochers, Patrick J. ;

Pulay, Peter ;

Vicic, David A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13175-13183