Aerobic and Electrochemical Oxidative Cross-Dehydrogenative-Coupling (CDC) Reaction in an Imidazolium-Based Ionic Liquid

被引：112

作者：

Basle, Olivier ^{[2
]}

Borduas, Nadine ^{[2
]}

Dubois, Pauline ^{[2
]}

Chapuzet, Jean Marc ^{[1
]}

Chan, Tak-Hang ^{[2
]}

Lessard, Jean ^{[1
]}

Li, Chao-Jun ^{[2
]}

机构：

[1] Univ Sherbrooke, Dept Chem, Sherbrooke, PQ J1K 2R1, Canada

[2] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 27期

基金：

加拿大创新基金会; 加拿大自然科学与工程研究理事会;

关键词：

cations; C-C coupling; C-H activation; ionic liquids; oxidation; SP(3) C-H; ANODIC CYANATION; BONDS ADJACENT; GENERATION; CATION; TETRAHYDROISOQUINOLINES; ALKYNYLATION; ALKYLATION; OXYGEN;

D O I：

10.1002/chem.201000240

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate [BMIm][BF4] has demonstrated high efficiency when applied as a solvent in the oxidative nitro-Mannich carbon-carbon bond formation. The copper-catalyzed cross-dehydrogenative coupling (CDC) between N-phenyltetrahydroisoquinoline and nitromethane in [BMIm][BF4] occurred with high yield under the described reaction conditions. Both the ionic liquid and copper catalyst were recycled nine times with almost no lost of activity. The electrochemical behavior of the tertiary amine substrate and beta-nitroamine product was investigated employing [BMIm]-[BF4] as electrolyte solvent. The potentiostatic electrolysis in ionic liquid afforded the desired product with a high yield. This result and the cyclic voltammetric investigation provide a better understanding of the reaction mechanism, which involves radical and iminium cation intermediates.

引用

页码：8162 / 8166

页数：5

共 48 条

[11] A kinetic study of the reaction between N,N-dimethyl-p-toluidine and its electrogenerated radical cation in a room temperature ionic liquid
Evans, RG
Compton, RG
[J]. CHEMPHYSCHEM, 2006, 7 (02) : 488 - 496
[12] The oxidation of alcohols in substituted imidazolium ionic liquids using ruthenium catalysts
Farmer, V
Welton, T
[J]. GREEN CHEMISTRY, 2002, 4 (02) : 97 - 102
[13] Reactivity of electrogenerated N-heterocyclic carbenes in room-temperature ionic liquids.: Cyclization to 2-azetidinone ring via C-3/C-4 bond formation
Feroci, Marta
Chiarotto, Isabella
Orsini, Monica
Sotgiu, Giovanni
Inesi, Achille
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (09) : 1355 - 1359
[14] Liquids intermediate between "molecular" and "ionic" liquids: Liquid Ion Pairs?
Fraser, Kevin J.
Izgorodina, Ekaterina I.
Forsyth, Maria
Scott, Janet L.
MacFarlane, Douglas R.
[J]. CHEMICAL COMMUNICATIONS, 2007, (37) : 3817 - 3819
[15] Anodic cyanation of C-4 hydroxylated piperidines:: total synthesis of (±)-alkaloid 241D
Girard, Nicolas
Hurvois, Jean-Pierre
[J]. TETRAHEDRON LETTERS, 2007, 48 (23) : 4097 - 4099
[16] Iron-catalyzed dehydrogenative phosphonation of N,N-dimethylanilines
Han, Wei
Ofial, Armin R.
[J]. CHEMICAL COMMUNICATIONS, 2009, (40) : 6023 - 6025
[17] Electrochemical reactivity in room-temperature ionic liquids
Hapiot, Philippe
Lagrost, Corinne
[J]. CHEMICAL REVIEWS, 2008, 108 (07) : 2238 - 2264
[18] DEPENDENCE OF ELECTRON-TRANSFER KINETICS OF THE FERROCENE/FERROCENIUM COUPLE ON THE VISCOSITY IN AMBIENT-TEMPERATURE CHLOROALUMINATE IONIC LIQUIDS
KARPINSKI, ZJ
SONG, S
OSTERYOUNG, RA
[J]. INORGANICA CHIMICA ACTA, 1994, 225 (1-2) : 9 - 14
[19] LeGall E, 1997, LIEBIGS ANN-RECL, P2089
[20] Cross-Dehydrogenative Coupling (CDC): Exploring C-C Bond Formations beyond Functional Group Transformations
Li, Chao-Jun
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (02) : 335 - 344

← 1 2 3 4 5 →