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

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 39期

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

页码：7859 / 7862

页数：4

共 43 条

[1] RECENT APPLICATIONS OF THE SHAPIRO REACTION
ADLINGTON, RM
BARRETT, AGM
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (02) : 55 - 59
[2] N-tosylhydrazones as reagents for cross-coupling reactions:: A route to polysubstituted olefins
Barluenga, José
Moriel, Patricia
Valdes, Carlos
Aznar, Fernando
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) : 5587 - 5590
[3] Reductive Azidation of Carbonyl Compounds via Tosylhydrazone Intermediates Using Sodium Azide
Barluenga, Jose
Tomas-Gamasa, Maria
Valdes, Carlos
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (24) : 5950 - 5952
[4] Straightforward Synthesis of Ethers: Metal-Free Reductive Coupling of Tosylhydrazones with Alcohols or Phenols
Barluenga, Jose
Tomas-Gamasa, Maria
Aznar, Fernando
Valdes, Carlos
[J]. 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
Barney, Rocky J.
Richardson, Rebekah M.
Wiemer, David F.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08) : 2875 - 2879
[7] ADDITION OF DIPHENYLPHOSPHINE OXIDE TO ARENESULFONYLHYDRAZONES - NOVEL ADDUCTS FROM TOSYLHYDRAZONES AND A NEW SYNTHESIS OF ALKYLDIPHENYLPHOSPHINE OXIDES FROM TRISYLHYDRAZONES
BERTZ, SH
DABBAGH, G
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (19) : 5932 - 5934
[8] New P-chirogenic phosphine ligands and their use in catalytic asymmetric reactions
Crépy, KVL
Imamoto, T
[J]. 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
Demmer, Charles S.
Krogsgaard-Larsen, Niels
Bunch, Lennart
[J]. 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
Feng, Xing-Wen
Wang, Jian
Zhang, Ji
Yang, Jing
Wang, Na
Yu, Xiao-Qi
[J]. ORGANIC LETTERS, 2010, 12 (19) : 4408 - 4411

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