A Ritter-Type Reaction: Direct Electrophilic Trifluoromethylation at Nitrogen Atoms Using Hypervalent Iodine Reagents

被引：129

作者：

Niedermann, Katrin ^{[1
]}

Frueh, Natalja ^{[1
]}

Vinogradova, Ekaterina ^{[1
]}

Wiehn, Matthias S. ^{[1
]}

Moreno, Aitor ^{[1
]}

Togni, Antonio ^{[1
]}

机构：

[1] Swiss Fed Inst Technol, Dept Chem & Angew Biowissensch, CH-8093 Zurich, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 05期

关键词：

electrophilic addition; hypervalent compounds; nitrogen heterocycles; synthetic methods; trifluoromethylation; SULFUR-TETRAFLUORIDE; FLUORINATION; DERIVATIVES; AMINES; ETHERS; SALTS; ACIDS;

D O I：

10.1002/anie.201006021

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Acid-catalyzed electrophilic trifluoromethylation of nitriles in the presence of azoles leads to N-(trifluoromethyl)imine derivatives. The source of the trifluoromethyl group is a readily prepared and easy-to-handle hypervalent iodine(III) reagent (see scheme; HNTf2=bis(N- (trifluoromethanesulfonyl)imide). This Ritter-type reaction is astraightforward approach to N-(trifluoromethyl)imidoyl azoles, compounds otherwise very difficult to access. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1059 / 1063

页数：5

共 24 条

[1] THE ELECTROCHEMICAL FLUORINATION OF NITROGEN-CONTAINING CARBOXYLIC-ACIDS - FLUORINATION OF DIMETHYLAMINO-SUBSTITUTED OR DIETHYLAMINO-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES
ABE, T
HAYASHI, E
BABA, H
FUKAYA, H
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1990, 48 (02) : 257 - 279
[2] [Anonymous], 2009, Angew. Chem., Int. Ed.
[3] Synthesis of sugar oxazolines by intramolecular Ritter-like reaction of D-fructose precursors
Blanco, JLJ
Rubio, EM
Mellet, CO
Fernández, JMG
[J]. SYNLETT, 2004, (12) : 2230 - 2232
[4] Brewer ARE, 2007, COMPR NAME REACT, P423
[5] THERMAL REACTIONS OF ALKYL N-CARBOMETHOXYSULFAMATE ESTERS
BURGESS, EM
PENTON, HR
TAYLOR, EA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) : 26 - 31
[6] N-Nitrosamide-mediated Ritter-type reactions.: Part II.: The operation of "persistent steric" and "π*-acceptor agostic-type" effects
Darbeau, RW
Pease, RS
Perez, EV
Gibble, RE
Ayo, FA
Sweeney, AW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2002, (12): : 2146 - 2153
[7] REACTION OF TERTIARY FORMAMIDES WITH SULFUR-TETRAFLUORIDE - DIRECT SYNTHESIS OF (TRIFLUOROMETHYL) AMINES
DMOWSKI, W
KAMINSKI, M
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1983, 23 (03) : 207 - 218
[8] Reactivity of a Hypervalent Iodine Trifluoromethylating Reagent toward THF: Ring Opening and Formation of Trifluoromethyl Ethers
Fantasia, Serena
Welch, Jan M.
Togni, Antonio
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05) : 1779 - 1782
[9] CHEMISTRY OF SULFUR TETRAFLUORIDE .6. FLUORINATION OF THIOCARBONYL COMPOUNDS
HARDER, RJ
SMITH, WC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (16) : 3422 - &
[10] NMR Study of the Tautomeric Behavior of N-(α-Aminoalkyl)tetrazoles
Katritzky, Alan R.
El-Gendy, Bahaa El-Dien M.
Draghici, Bogdan
Hall, C. Dennis
Steel, Peter J.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (19) : 6468 - 6476

← 1 2 3 →