Cross-Coupling Hydrogen Evolution by Visible Light Photocatalysis Toward C(sp2)-P Formation: Metal-Free C-H Functionalization of Thiazole Derivatives with Diarylphosphine Oxides

被引:152
作者
Luo, Kai [1 ,2 ,3 ]
Chen, Yao-Zhong [1 ,2 ,3 ]
Yang, Wen-Chao [1 ,2 ]
Zhu, Jie [1 ,2 ]
Wu, Lei [1 ,2 ]
机构
[1] Nanjing Agr Univ, Coll Sci, Jiangsu Key Lab Pesticide Sci, Nanjing 210095, Jiangsu, Peoples R China
[2] Nanjing Agr Univ, Coll Sci, Dept Chem, Nanjing 210095, Jiangsu, Peoples R China
[3] Nanjing Agr Univ, Coll Plant Protect, Nanjing 210095, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
PALLADIUM-CATALYZED PHOSPHONATION; P BOND FORMATION; PHOTOREDOX CATALYSIS; STEREOSELECTIVE-SYNTHESIS; ROOM-TEMPERATURE; ARYL MESYLATES; ARYLATION; PHOSPHORYLATION; EFFICIENT; ACIDS;
D O I
10.1021/acs.orglett.5b03497
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Visible light along with 5 mol % eosin B catalyzed the first direct C-H phosphorylation of thiazole derivatives with diarylphosphine oxides by a photoredox process in the absence of an external oxidant. The scope of thiazoles and phosphine oxides was further investigated, as was functional group tolerance. The general and operational simplicity provides a novel metal and oxidant-free alternative for the formation of heteroaryl-P bonds, and only molecular hydrogen is generated as a byproduct.
引用
收藏
页码:452 / 455
页数:4
相关论文
共 65 条
[21]   Synthesis of Highly Functionalized Polycyclic Quinoxaline Derivatives Using Visible-Light Photoredox Catalysis [J].
He, Zhi ;
Bae, Minwoo ;
Wu, Jie ;
Jamison, Timothy F. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (52) :14451-14455
[22]   Palladium-catalyzed direct phosphonation of azoles with dialkyl phosphites [J].
Hou, Chaodong ;
Ren, Yunlai ;
Lang, Rui ;
Hu, Xiaoxue ;
Xia, Chungu ;
Li, Fuwei .
CHEMICAL COMMUNICATIONS, 2012, 48 (42) :5181-5183
[23]   Visible-Light-Promoted Iminyl-Radical Formation from Acyl Oximes: A Unified Approach to Pyridines, Quinolines, and Phenanthridines [J].
Jiang, Heng ;
An, Xiaode ;
Tong, Kun ;
Zheng, Tianyi ;
Zhang, Yan ;
Yu, Shouyun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (13) :4055-4059
[24]   Direct α-Arylation of Ethers through the Combination of Photoredox-Mediated C-H Functionalization and the Minisci Reaction [J].
Jin, Jian ;
MacMillan, David W. C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (05) :1565-1569
[25]   Novel, Stereoselective and Stereospecific Synthesis of Allenylphosphonates and Related Compounds via Palladium-Catalyzed Propargylic Substitution [J].
Kalek, Marcin ;
Stawinski, Jacek .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (10) :1741-1755
[26]   Palladium-Catalyzed Propargylic Substitution with Phosphorus Nucleophiles: Efficient, Stereoselective Synthesis of Allenylphosphonates and Related Compounds [J].
Kalek, Marcin ;
Johansson, Tommy ;
Jezowska, Martina ;
Stawinski, Jacek .
ORGANIC LETTERS, 2010, 12 (20) :4702-4704
[27]   Tin(IV) phosphonates: porous nanoparticles and pillared materials [J].
Kirumakki, Sharath ;
Huang, Jin ;
Subbiah, Ayyappan ;
Yao, Jiyong ;
Rowland, Adam ;
Smith, Brentley ;
Mukherjee, Atashi ;
Samarajeewa, Sandani ;
Clearfield, Abraham .
JOURNAL OF MATERIALS CHEMISTRY, 2009, 19 (17) :2593-2603
[28]   Pyridine-Directed Palladium-Catalyzed Phosphonation of C(sp2)-H Bonds [J].
Li, Changkun ;
Yano, Takaaki ;
Ishida, Naoki ;
Murakami, Masahiro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) :9801-9804
[29]   Visible-Light-Promoted Vinylation of Tetrahydrofuran with Alkynes through Direct C-H Bond Functionalization [J].
Li, Jing ;
Zhang, Jing ;
Tan, Haibo ;
Wang, David Zhigang .
ORGANIC LETTERS, 2015, 17 (10) :2522-2525
[30]   Aerobic Transition-Metal-Free Visible-Light Photoredox Indole C-3 Formylation Reaction [J].
Li, Xiang ;
Gu, Xiangyong ;
Li, Yongjuan ;
Li, Pixu .
ACS CATALYSIS, 2014, 4 (06) :1897-1900