Transition-metal-free dehydrogenation coupling of pyridinium through a self-promoted hydride transfer process

被引:6
作者
Shang, Wenbin [1 ,3 ]
Li, Shanyong [1 ,3 ]
Ding, Yuzhen [2 ]
Pan, Zhiqiang [2 ]
Tong, Xiaogang [2 ]
Xia, Chengfeng [1 ,2 ]
机构
[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, 132 Lanhei Rd, Kunming 650201, Yunnan, Peoples R China
[2] Yunnan Univ, Sch Chem Sci & Technol, Minist Educ, Key Lab Med Chem Nat Resources, 2 North Cuihu Rd, Kunming 650091, Yunnan, Peoples R China
[3] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H FUNCTIONALIZATION; HYDROGEN EVOLUTION REACTION; QUINOLINE N-OXIDES; DIRECT ARYLATION; SELECTIVE ALKENYLATION; ALPHA-ARYLATION; ALKYLATION; DERIVATIVES; PHOTOREDOX; CHEMISTRY;
D O I
10.1039/c7qo00389g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A transition-metal-free intramolecular cross dehydrogenation coupling reaction of pyridinium was developed. The C(sp(2))-H/C(sp(2))-H coupling reaction involved an unprecedented intermolecular hydride transfer process from the 1,2-dihydropyridine intermediate to another molecule of pyridinium and formed 1,4-dihydropyridine. Unlike the well-known dehydrogenation coupling proceeded under oxidative conditions, this was the first example of the coupling reaction through a substrate self-promoted hydride transfer process.
引用
收藏
页码:1789 / 1793
页数:5
相关论文
共 69 条
[51]   Metal-Free Oxidative Decarbonylative Coupling of Aliphatic Aldehydes with Azaarenes: Successful Minisci-Type Alkylation of Various Heterocycles [J].
Tang, Ren-Jin ;
Kang, Lei ;
Yang, Luo .
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (09) :2055-2060
[52]   Transition-Metal-Free Intramolecular N-Arylations [J].
Thome, Isabelle ;
Bolm, Carsten .
ORGANIC LETTERS, 2012, 14 (07) :1892-1895
[53]  
VANBERGEN TJ, 1971, J ORG CHEM, V36, P1705
[54]   CHEMISTRY OF DIHYDROPYRIDINES .5. HYDRIDE TRANSFER FROM 1,4-DIHYDROPYRIDINES TO PYRIDINIUM SALTS - ASSESSMENT OF STRUCTURAL AND ENERGETIC FACTORS WITH HANTZSCH ESTER DERIVED COMPOUNDS [J].
VANBERGEN, TJ ;
MULDER, T ;
VANDERVEEN, RA ;
KELLOGG, RM .
TETRAHEDRON, 1978, 34 (15) :2377-2383
[55]  
Wills M., 2016, HYDROGEN TRANSFER RE, P69
[56]   Activation of C-H Bonds through Oxidant-Free Photoredox Catalysis: Cross-Coupling Hydrogen-Evolution Transformation of Isochromans and β-Keto Esters [J].
Xiang, Ming ;
Meng, Qing-Yuan ;
Li, Jia-Xin ;
Zheng, Yi-Wen ;
Ye, Chen ;
Li, Zhi-Jun ;
Chen, Bin ;
Tung, Chen-Ho ;
Wu, Li-Zhu .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (50) :18080-18084
[57]   Construction of Tetracyclic 3-Spirooxindole through Cross-Dehydrogenation of Pyridinium: Applications in Facile Synthesis of (±)-Corynoxine and (±)-Corynoxine B [J].
Xu, Jun ;
Shao, Li-Dong ;
Li, Dashan ;
Deng, Xu ;
Liu, Yu-Chen ;
Zhao, Qin-Shi ;
Xia, Chengfeng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (52) :17962-17965
[58]   Aerobic, Transition-Metal-Free, Direct, and Regiospecific Mono-α-arylation of Ketones: Synthesis and Mechanism by DFT Calculations [J].
Xu, Qing-Long ;
Gao, Hongyin ;
Yousufuddin, Muhammed ;
Ess, Daniel H. ;
Kuerti, Laszlo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (38) :14048-14051
[59]   Regiodivergent Cross-Dehydrogenative Coupling of Pyridines and Benzoxazoles: Discovery of Organic Halides as Regio-Switching Oxidants [J].
Yamada, Shuya ;
Murakami, Kei ;
Itami, Kenichiro .
ORGANIC LETTERS, 2016, 18 (10) :2415-2418
[60]   Palladium-Catalyzed C-H Oxidation of Isoquinoline N-Oxides: Selective Alkylation with Dialkyl Sulfoxides and Halogenation with Dihalo sulfoxides [J].
Yao, Bo ;
Song, Ren-Jie ;
Liu, Yan ;
Xie, Ye-Xiang ;
Li, Jin-Heng ;
Wang, Meng-Ke ;
Tang, Ri-Yuan ;
Zhang, Xing-Guo ;
Deng, Chen-Liang .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (10) :1890-1896