Regioselective direct oxidative C-H cyanation of quinoline and its derivatives catalyzed by vanadium-containing heteropoly acids

被引：18

作者：

Yamaguchi, Kazuya ^{[1
]}

Xu, Ning ^{[1
]}

Jin, Xiongjie ^{[1
]}

Suzuki, Kosuke ^{[1
]}

Mizuno, Noritaka ^{[1
]}

机构：

[1] Univ Tokyo, Sch Engn, Dept Appl Chem, Bunkyo Ku, Tokyo 1138656, Japan

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 49期

关键词：

EFFICIENT HETEROGENEOUS CATALYST; PRIMARY AMIDES; ARYL HALIDES; AEROBIC OXIDATION; NITRILES; AMINES; FUNCTIONALIZATION; AMMOXIDATION; DEHYDRATION; OXYGEN;

D O I：

10.1039/c5cc02797g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A direct oxidative C-H cyanation of quinoline and its derivatives using trimethylsilyl cyanide as the cyano source and molecular oxygen as the terminal oxidant has been developed. In the presence of catalytic amounts of vanadium-containing heteropoly acids, e.g., H7PV4Mo8O40, cyanation of various quinoline and its derivatives preferentially took place at the 4-position, affording the corresponding substituted 4-cyanoquinolines as the major products.

引用

页码：10034 / 10037

页数：4

共 51 条

[1] DIRECT INTRODUCTION OF NITRILES VIA USE OF UNSTABLE REISSERT INTERMEDIATES - CONVENIENT PROCEDURES FOR THE PREPARATION OF 2-CYANOQUINOLINES AND 1-CYANOISOQUINOLINES
BOGER, DL
BROTHERTON, CE
PANEK, JS
YOHANNES, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) : 4056 - 4058
[2] Reagents for organic synthesis: Use of organostannyl oxides as catalytic neutral agents in the preparation of nitriles from primary amides under microwave irradiation
Bose, DS
Jayalakshmi, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05) : 1713 - 1714
[3] Looking on heterogeneous catalytic systems from different perspectives:: Multitechnique approaches as a new challenge for in situ studies
Brückner, A
[J]. CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 2003, 45 (01): : 97 - 150
[4] Mild Palladium-Catalyzed Cyanation of (Hetero)aryl Halides and Triflates in Aqueous Media
Cohen, Daniel T.
Buchwald, Stephen L.
[J]. ORGANIC LETTERS, 2015, 17 (02) : 202 - 205
[5] Novel ruthenium-terpyridyl complex for direct oxidation of amines to nitriles
Cristian, Liliana
Nica, Simona
Pavel, Octavian D.
Mihailciuc, Constantin
Almasan, Valer
Coman, Simona M.
Hardacre, Christopher
Parvulescu, Vasile I.
[J]. CATALYSIS SCIENCE & TECHNOLOGY, 2013, 3 (10) : 2646 - 2653
[6] Direct Transformation of N,N-Dimethylformamide to -CN: Pd-Catalyzed Cyanation of Heteroarenes via C-H Functionalization
Ding, Shengtao
Jiao, Ning
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (32) : 12374 - 12377
[7] CYANATION OF AROMATIC HALIDES
ELLIS, GP
ROMNEYALEXANDER, TM
[J]. CHEMICAL REVIEWS, 1987, 87 (04) : 779 - 794
[8] Fatiadi A.J., 1983, Preparation and Synthetic Applications of Cyano Compounds
[9] Synthesis and Late-Stage Functionalization of Complex Molecules through C-H Fluorination and Nucleophilic Aromatic Substitution
Fier, Patrick S.
Hartwig, John F.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (28) : 10139 - 10147
[10] Selective C-H Fluorination of Pyridines and Diazines Inspired by a Classic Amination Reaction
Fier, Patrick S.
Hartwig, John F.
[J]. SCIENCE, 2013, 342 (6161) : 956 - 960

← 1 2 3 4 5 6 →