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

[11] Rhodium-Catalyzed Directed C-H Cyanation of Arenes with N-Cyano-N-phenyl-p-toluenesulfonamide
Gong, Tian-Jun
Xiao, Bin
Cheng, Wan-Min
Su, Wei
Xu, Jun
Liu, Zhao-Jing
Liu, Lei
Fu, Yao
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (29) : 10630 - 10633
[12] Triselenium Dicyanide (TSD) as a New Cyanation Reagent: Synthesis of Cyano Pterins and Quinoxalines Along with Library of Cyano N-Heterocyclic Compounds
Goswami, Shyamaprosad
Maity, Annada C.
Das, Nirmal K.
Sen, Debabrata
Maity, Sibaprasad
[J]. SYNTHETIC COMMUNICATIONS, 2009, 39 (03) : 407 - 415
[13] Hill C.L., 2004, COMPREHENSIVE COORDI, V4, P679, DOI DOI 10.1016/B0-08-043748-6/03036-X
[14] HOMOGENEOUS CATALYSIS BY TRANSITION-METAL OXYGEN ANION CLUSTERS
HILL, CL
PROSSERMCCARTHA, CM
[J]. COORDINATION CHEMISTRY REVIEWS, 1995, 143 : 407 - 455
[15] Introduction: Polyoxometalates - Multicomponent molecular vehicles to probe fundamental issues and practical problems
Hill, CL
[J]. CHEMICAL REVIEWS, 1998, 98 (01) : 1 - 2
[16] Metal oxide-catalyzed ammoxidation of alcohols to nitriles and promotion effect of gold nanoparticles for one-pot amide synthesis
Ishida, Tamao
Watanabe, Hiroto
Takei, Takashi
Hamasaki, Akiyuki
Tokunaga, Makoto
Haruta, Masatake
[J]. APPLIED CATALYSIS A-GENERAL, 2012, 425 : 85 - 90
[17] Ishihara K, 2002, ANGEW CHEM INT EDIT, V41, P2983, DOI 10.1002/1521-3773(20020816)41:16<2983::AID-ANIE2983>3.0.CO
[18] 2-X
[19] A Monovacant Lacunary Silicotungstate as an Efficient Heterogeneous Catalyst for Dehydration of Primary Amides to Nitriles
Itagaki, Shintaro
Kamata, Keigo
Yamaguchi, Kazuya
Mizuno, Noritaka
[J]. CHEMCATCHEM, 2013, 5 (07) : 1725 - 1728
[20] Electron Transfer-Oxygen Transfer Oxygenation of Sulfides Catalyzed by the H5PV2Mo10O40 Polyoxometalate
Khenkin, Alexander M.
Leitus, Gregory
Neumann, Ronny
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (33) : 11446 - 11448

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