Mild and efficient oxidation of phosphorus(III) compounds with Selectfluor

被引:11
作者
Chen, Qian [1 ]
Zeng, Jiekun [1 ]
Yan, Xinxing [1 ]
Huang, Yulin [1 ]
Du, Zhiyun [1 ]
Zhang, Kun [1 ]
Wen, Chunxiao [1 ]
机构
[1] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
Phosphines; Phosphine oxides; Oxidation; Selectfluor; SECONDARY PHOSPHINE OXIDES; ENANTIOSELECTIVE HYDROGENATION; ASYMMETRIC HYDROGENATION; ELECTRON-TRANSFER; RADICAL CATIONS; LIGANDS; REDUCTION; TRIPHENYLPHOSPHINE; OXYGEN; DERIVATIVES;
D O I
10.1016/j.tetlet.2016.06.078
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and efficient oxidation of phosphorus(III) compounds with Selectfluor is described. The reactions smoothly led to the formation of tertiary phosphine oxides, phosphinates, and phosphonates in up to 99% yield under mild conditions in minutes. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3379 / 3381
页数:3
相关论文
共 64 条
[1]   Chiral phosphine oxides in present-day organocatalysis [J].
Benaglia, Maurizio ;
Rossi, Sergio .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (17) :3824-3830
[2]   New perfluoroalkylated BINAP usable as a ligand in homogeneous and supercritical carbon dioxide asymmetric hydrogenation [J].
Berthod, M ;
Mignani, G ;
Lemaire, M .
TETRAHEDRON-ASYMMETRY, 2004, 15 (07) :1121-1126
[3]   4,4′ and 5,5′-DiamBINAP as a hydrosoluble chiral ligand:: syntheses and use in Ru(II) asymmetric biphasic catalytic hydrogenation [J].
Berthod, M ;
Saluzzo, C ;
Mignani, G ;
Lemaire, M .
TETRAHEDRON-ASYMMETRY, 2004, 15 (04) :639-645
[4]   THE MICHAELIS-ARBUZOV REARRANGEMENT [J].
BHATTACHARYA, AK ;
THYAGARAJAN, G .
CHEMICAL REVIEWS, 1981, 81 (04) :415-430
[5]  
Borner A., 2008, Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications
[6]   Reduction of tertiary phosphine oxides with DIBAL-H [J].
Busacca, Carl A. ;
Raju, Ravinder ;
Grinberg, Nelu ;
Haddad, Nizar ;
James-Jones, Paul ;
Lee, Heewon ;
Lorenz, Jon C. ;
Saha, Anjan ;
Senanayake, Chris H. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (04) :1524-1531
[7]   Monofluorination of Organic Compounds: 10 Years of Innovation [J].
Champagne, Pier Alexandre ;
Desroches, Justine ;
Hamel, Jean-Denys ;
Vandamme, Mathilde ;
Paquin, Jean-Francois .
CHEMICAL REVIEWS, 2015, 115 (17) :9073-9174
[8]   P-Arylation of Dialkyl Phosphites and Secondary Phosphine Oxides with Arynes [J].
Chen, Qian ;
Yan, Xinxing ;
Du, Zhiyun ;
Zhang, Kun ;
Wen, Chunxiao .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (01) :276-281
[9]  
Cho CS, 1998, POLYM INT, V47, P203, DOI 10.1002/(SICI)1097-0126(1998100)47:2<203::AID-PI55>3.0.CO
[10]  
2-X