Co(III)-Catalyzed Synthesis of Quinazolines via C-H Activation of N-Sulfinylimines and Benzimidates

被引:168
作者
Wang, Fen [1 ]
Wang, He [1 ]
Wang, Qiang [1 ]
Yu, Songjie [1 ]
Li, Xingwei [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
关键词
ONE-POT SYNTHESIS; BOND-FORMATION; COBALT(III)-CATALYZED ARYL; DIAZO-COMPOUNDS; AMIDATION; FUNCTIONALIZATION; AMINATION; ALKYNES; ACCESS; ARENES;
D O I
10.1021/acs.orglett.6b00227
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
C-H activation of arenes has been established as an important strategy for heterocycle synthesis via annulations between arenes and unsaturated coupling partners. However, nitriles failed to act as such a coupling partner. Dioxazolones have been employed as a synthon of nitriles, and subsequent coupling with arenes such as N-sulfinylimines and benzimidates bearing a functionalizable directing group provided facile access to two classes of quinazolines under Co(III)-catalysis.
引用
收藏
页码:1306 / 1309
页数:4
相关论文
共 74 条
[51]   Rh(III)-Catalyzed Synthesis of Multisubstituted Isoquinoline and Pyridine N-Oxides from Oximes and Diazo Compounds [J].
Shi, Zhuangzhi ;
Koester, Dennis C. ;
Boultadakis-Arapinis, Melissa ;
Glorius, Frank .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (33) :12204-12207
[52]   On the Interpretation of Deuterium Kinetic Isotope Effects in C?H Bond Functionalizations by Transition-Metal Complexes [J].
Simmons, Eric M. ;
Hartwig, John F. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (13) :3066-3072
[53]   Substrate Activation Strategies in Rhodium(III)-Catalyzed Selective Functionalization of Arenes [J].
Song, Guoyong ;
Li, Xingwei .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (04) :1007-1020
[54]   C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation [J].
Song, Guoyong ;
Wang, Fen ;
Li, Xingwei .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) :3651-3678
[55]   Exploration of Earth-Abundant Transition Metals (Fe, Co, and Ni) as Catalysts in Unreactive Chemical Bond Activations [J].
Su, Bo ;
Cao, Zhi-Chao ;
Shi, Zhang-Jie .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (03) :886-896
[56]   Cp*CoIII Catalyzed Site-Selective CH Activation of Unsymmetrical O-Acyl Oximes: Synthesis of Multisubstituted Isoquinolines from Terminal and Internal Alkynes [J].
Sun, Bo ;
Yoshino, Tatsuhiko ;
Kanai, Motomu ;
Matsunaga, Shigeki .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (44) :12968-12972
[57]   A Cp*CoI2-dimer as a precursor for cationic Co(III)-catalysis: application to C-H phosphoramidation of indoles [J].
Sun, Bo ;
Yoshino, Tatsuhiko ;
Matsunaga, Shigeki ;
Kanai, Motomu .
CHEMICAL COMMUNICATIONS, 2015, 51 (22) :4659-4661
[58]   Air-Stable Carbonyl(pentamethylcyclopentadienyl)cobalt Diiodide Complex as a Precursor for Cationic (Pentamethylcyclopentadienyl)cobalt(III) Catalysis: Application for Directed C-2 Selective C-H Amidation of Indoles [J].
Sun, Bo ;
Yoshino, Tatsuhiko ;
Matsunaga, Shigeki ;
Kanai, Motomu .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) :1491-1495
[59]   Direct C-H Transformation via Iron Catalysis [J].
Sun, Chang-Liang ;
Li, Bi-Jie ;
Shi, Zhang-Jie .
CHEMICAL REVIEWS, 2011, 111 (03) :1293-1314
[60]   Dehydrative Direct C-H Allylation with Allylic Alcohols under [Cp*CoIII] Catalysis [J].
Suzuki, Yudai ;
Sun, Bo ;
Sakata, Ken ;
Yoshino, Tatsuhiko ;
Matsunaga, Shigeki ;
Kanai, Motomu .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (34) :9944-9947