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

[21]

Quin L. D., 2000, GUIDE ORGANOPHOSPHOR

[22] Lewis acid catalyzed room-temperature Michaelis-Arbuzov rearrangement [J].

Renard, PY ;

Vayron, P ;

Leclerc, E ;

Valleix, A ;

Mioskowski, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (21) :2389-2392

[23] COPPER(I) CATALYSIS IN CYCLOPROPANATIONS WITH DIAZO-COMPOUNDS - ROLE OF OLEFIN COORDINATION [J].

SALOMON, RG ;

KOCHI, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (10) :3300-3310

[24] N-Tosylhydrazones: versatile reagents for metal-catalyzed and metal-free cross-coupling reactions [J].

Shao, Zhihui ;

Zhang, Hongbin .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (02) :560-572

[25] AN INVESTIGATION OF INTERMEDIATES IN BASE-CATALYZED DECOMPOSITION OF CAMPHOR TOSYLHYDRAZONE IN APROTIC SOLVENTS [J].

SHAPIRO, RH ;

DUNCAN, JH ;

CLOPTON, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (02) :471-&

[26] HClO4-SiO2 as a Novel and Recyclable Catalyst for the Phospha-Michael Addition of Phosphorous Nucleophiles to α,β-Unsaturated Malonates [J].

Sobhani, Sara ;

Rezazadeh, Soodabeh .

SYNLETT, 2010, (10) :1485-1488

[27] Hydrophosphorylation of alkenes with dialkyl phosphites catalyzed by Mn(III) under air [J].

Tayama, O ;

Nakano, A ;

Iwahama, T ;

Sakaguchi, S ;

Ishii, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5494-5496

[28] Expeditious synthesis of 1,1-diarylethylenes related to isocombretastatin A-4 (isoCA-4) via palladium-catalyzed arylation of N-tosylhydrazones with aryl triflates [J].

Treguier, Bret ;

Hamze, Abdallah ;

Provot, Olivier ;

Brion, Jean-Daniel ;

Alami, Mouad .

TETRAHEDRON LETTERS, 2009, 50 (47) :6549-6552

[29] Air-stable and highly active dendritic phosphine oxide-stabilized palladium nanoparticles: Preparation, characterization and applications in the carbon-carbon bond formation and hydrogenation reactions [J].

Wu, Lei ;

Li, Zhi-Wei ;

Zhang, Feng ;

He, Yan-Mei ;

Fan, Qing-Hua .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (06) :846-862

[30] Phosphine dendrimer-stabilized palladium nanoparticles, a highly active and recyclable catalyst for the Suzuki-Miyaura reaction and hydrogenation [J].

Wu, Lei ;

Li, Bao-Lin ;

Huang, Yi-Yong ;

Zhou, Hai-Feng ;

He, Yan-Mei ;

Fan, Qing-Hua .

ORGANIC LETTERS, 2006, 8 (16) :3605-3608

← 1 2 3 4 5 →