Organoselenium-catalyzed vicinal dichlorination of unsaturated phosphonates

被引：5

作者：

Zeng, Xianghua ^{[1
]}

Gong, Chunhua ^{[1
]}

Zhang, Junyong ^{[1
]}

Xie, Jingli ^{[1
,2
]}

机构：

[1] Jiaxing Univ, Coll Biol Chem Sci & Engn, Jiaxing 314001, Peoples R China

[2] Nanjing Univ, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China

来源：

NEW JOURNAL OF CHEMISTRY | 2016年 / 40卷 / 09期

基金：

中国国家自然科学基金;

关键词：

RENIN INHIBITORS; OLEFINS; FUNCTIONALIZATION; ALKENES; DIBROMINATION; REAGENTS; DEHALOGENATION; DIHALOGENATION; HALOGENATION; ALCOHOLS;

D O I：

10.1039/c6nj00658b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Diphenyl diselenide (PhSeSePh) was effective as a pre-catalyst for the vicinal dichlorination of alpha,beta-unsaturated phosphonates with sulfuryl chloride. The reaction conditions were mild and the desired products were formed in up to 93% yield and moderate diastereoselectivity (10:1). The important diphenylselenium dichloride intermediate was obtained and characterized by X-ray crystallography.

引用

页码：7866 / 7871

页数：6

共 47 条

[1] Comparative study of the vicinal functionalization of olefins with 2:1 bromide/bromate and iodide/iodate reagents [J].

Agrawal, Manoj K. ;

Adimurthy, Subbarayappa ;

Ganguly, Bishwajit ;

Ghosh, Pushpito K. .

TETRAHEDRON, 2009, 65 (14) :2791-2797

[2] Isoselenazolones as Catalysts for the Activation of Bromine: Bromolactonization of Alkenoic Acids and Oxidation of Alcohols [J].

Balkrishna, Shah Jaimin ;

Prasad, Ch Durga ;

Panini, Piyush ;

Detty, Michael R. ;

Chopra, Deepak ;

Kumar, Sangit .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (21) :9541-9552

[3] OXIDATION OF ACETYLENES WITH TERT-BUTYL HYDROPEROXIDE CATALYZED BY SELENIUM DIOXIDE - ALPHA,ALPHA'-DIOXYGENATION OF INTERNAL ALKYNES [J].

CHABAUD, B ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4202-4204

[4] TRIFLUOROACETIC ACID CATALYZED REACTION OF IODOBENZENE DICHLORIDE WITH ETHYLENIC COMPOUNDS [J].

COTTER, JL ;

ANDREWS, LJ ;

KEEFER, RM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (05) :793-&

[5] A straightforward entry into enantiomerically enriched β-amino-α-hydroxyphosphonic acid derivatives [J].

Cravotto, G ;

Giovenzana, GB ;

Pagliarin, R ;

Palmisano, G ;

Sisti, M .

TETRAHEDRON-ASYMMETRY, 1998, 9 (05) :745-748

[6] Catalytic, Stereoselective Dihalogenation of Alkenes: Challenges and Opportunities [J].

Cresswell, Alexander J. ;

Eey, Stanley T. -C. ;

Denmark, Scott E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (52) :15642-15682

[7]

Cresswell AJ, 2015, NAT CHEM, V7, P146, DOI [10.1038/NCHEM.2141, 10.1038/nchem.2141]

[8] Hydromethylation of Unactivated Olefins [J].

Dao, Hai T. ;

Li, Chao ;

Michaudel, Quentin ;

Maxwell, Brad D. ;

Baran, Phil S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (25) :8046-8049

[9]

De Kimpe N., 1990, CHEM ALPHA HALOKETON

[10] Catalytic Asymmetric Thiofunctionalization of Unactivated Alkenes [J].

Denmark, Scott E. ;

Kornfilt, David J. P. ;

Vogler, Thomas .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (39) :15308-15311

← 1 2 3 4 5 →