A novel copper-catalyzed reductive coupling of N-tosylhydrazones with H-phosphorus oxides

被引:63
作者
Wu, Lei [1 ,2 ]
Zhang, Xiao [2 ]
Chen, Qing-Qing [2 ]
Zhou, An-Kun [2 ]
机构
[1] Nanjing Agr Univ, Coll Sci, Dept Chem, Nanjing 210095, Jiangsu, Peoples R China
[2] Harbin Inst Technol, Acad Fundamental & Interdisciplinary Sci, Harbin 150080, Peoples R China
基金
中国国家自然科学基金;
关键词
STABILIZED PALLADIUM NANOPARTICLES; DIPHENYLPHOSPHINE OXIDE; RECYCLABLE CATALYST; DIAZO-COMPOUNDS; BOND FORMATION; HYDROPHOSPHORYLATION; NICKEL; REAGENTS; ALCOHOLS; ALKYNES;
D O I
10.1039/c2ob26414e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report here a novel C(sp(3))-P bonds formation via copper-catalyzed reductive coupling of N-tosylhydrazones with H-phosphorus oxides. A variety of aliphatic and aromatic substrates bearing electron-rich and electron-deficient substituents affords phosphine oxide derivatives with moderate to good yields. This work suggests a new transformation of aldehydes/ketones via N-tosylhydrazones to organophosphorus compounds.
引用
收藏
页码:7859 / 7862
页数:4
相关论文
共 43 条
[1]   RECENT APPLICATIONS OF THE SHAPIRO REACTION [J].
ADLINGTON, RM ;
BARRETT, AGM .
ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (02) :55-59
[2]   N-tosylhydrazones as reagents for cross-coupling reactions:: A route to polysubstituted olefins [J].
Barluenga, José ;
Moriel, Patricia ;
Valdes, Carlos ;
Aznar, Fernando .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5587-5590
[3]   Reductive Azidation of Carbonyl Compounds via Tosylhydrazone Intermediates Using Sodium Azide [J].
Barluenga, Jose ;
Tomas-Gamasa, Maria ;
Valdes, Carlos .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (24) :5950-5952
[4]   Straightforward Synthesis of Ethers: Metal-Free Reductive Coupling of Tosylhydrazones with Alcohols or Phenols [J].
Barluenga, Jose ;
Tomas-Gamasa, Maria ;
Aznar, Fernando ;
Valdes, Carlos .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (29) :4993-4996
[5]  
Barluenga J, 2009, NAT CHEM, V1, P494, DOI [10.1038/NCHEM.328, 10.1038/nchem.328]
[6]   Direct Conversion of Benzylic and Allylic Alcohols to Phosphonates [J].
Barney, Rocky J. ;
Richardson, Rebekah M. ;
Wiemer, David F. .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08) :2875-2879
[8]   New P-chirogenic phosphine ligands and their use in catalytic asymmetric reactions [J].
Crépy, KVL ;
Imamoto, T .
NEW ASPECTS IN PHOSPHORUS CHEMISTRY III, 2003, 229 :1-40
[9]   Review on Modern Advances of Chemical Methods for the Introduction of a Phosphonic Acid Group [J].
Demmer, Charles S. ;
Krogsgaard-Larsen, Niels ;
Bunch, Lennart .
CHEMICAL REVIEWS, 2011, 111 (12) :7981-8006
[10]   Copper-Catalyzed Nitrogen Loss of Sulfonylhydrazones: A Reductive Strategy for the Synthesis of Sulfones from Carbonyl Compounds [J].
Feng, Xing-Wen ;
Wang, Jian ;
Zhang, Ji ;
Yang, Jing ;
Wang, Na ;
Yu, Xiao-Qi .
ORGANIC LETTERS, 2010, 12 (19) :4408-4411