An Efficient Synthesis of Vinyl Sulfones from Alkenes and Aryl Sulfinates

被引：40

作者：

Das, Biswanath ^{[1
]}

Lingaiah, Maram ^{[1
]}

Damodar, Kongara ^{[1
]}

Bhunia, Nisith ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India

来源：

SYNTHESIS-STUTTGART | 2011年 / 18期

关键词：

vinylsulfone; alkene; aryl sulfinate; synthetic methods; ADDITION REACTIONS; HYDROGENOLYSIS; CHEMISTRY; OLEFINS; ACCESS;

D O I：

10.1055/s-0030-1260142

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vinyl sulfones have been efficiently synthesized by treatment of alkenes with sodium arene sulfinates using potassium iodide and sodium periodate in the presence of a catalytic amount of acetic acid at room temperature. The products are formed in high yields (87-95%) within 2.5-8 hours.

引用

页码：2941 / 2944

页数：4

共 18 条

[1] SYNTHESIS USING SULFONES .24. STEREOSELECTIVE SYNTHESIS OF OLEFINS BY HYDROGENOLYSIS OF VINYLSULFONES [J].

BREMNER, J ;

JULIA, M ;

LAUNAY, M ;

STACINO, JP .

TETRAHEDRON LETTERS, 1982, 23 (32) :3265-3266

[2] TOTAL SYNTHESIS OF THE CEPHALOTAXUS ALKALOIDS DL-CEPHALOTAXINE, DL-11-HYDROXYCEPHALOTAXINE, AND DL-DRUPACINE [J].

BURKHOLDER, TP ;

FUCHS, PL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9601-9613

[3] Unsymmetrical diaryl sulfones and aryl vinyl sulfones through palladium-catalyzed coupling of aryl and vinyl halides or triflates with sulfinic acid salts [J].

Cacchi, S ;

Fabrizi, G ;

Goggiamani, A ;

Parisi, LM ;

Bernini, R .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5608-5614

[4] SYNTHESES WITH SULFONES .47. STEREOSELECTIVE ACCESS TO 1,3-DIENES AND 1,4-DIENES THROUGH HYDROGENOLYSIS OF BENZENESULFONYLDIENES - APPLICATION TO PHEROMONE SYNTHESIS [J].

CUVIGNY, T ;

DUPENHOAT, CH ;

JULIA, M .

TETRAHEDRON, 1987, 43 (05) :859-872

[5] Copper(II) Oxide Catalyzed Ligand-Free Coupling Reaction of Heteroarenes with Bromoalkynes [J].

Das, Biswanath ;

Reddy, Gandolla Chinna ;

Balasubramanyam, Penagaluri ;

Salvanna, N. .

SYNTHESIS-STUTTGART, 2011, (05) :816-820

[6] A Simple, Advantageous Synthesis of 5-Substituted 1H-Tetrazoles ( 391, 2010) [J].

Das, Biswanath ;

Reddy, Cheruku Ravindra ;

Kumar, Duddukuri Nandan ;

Krishnaiah, Martha ;

Narender, Ravirala .

SYNLETT, 2010, (03) :E3-E3

[7] A Simple and Efficient Access to α-Amino Phosphonates from N-Benzyloxycarbonylamino Sulfones Using Indium(III) Chloride [J].

Das, Biswanath ;

Damodar, Kongara ;

Bhunia, Nisith .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5607-5609

[8] THE ROLE OF SULFUR FUNCTIONALITIES IN ACTIVATING AND DIRECTING OLEFINS IN CYCLO-ADDITION REACTIONS [J].

DELUCCHI, O ;

PASQUATO, L .

TETRAHEDRON, 1988, 44 (22) :6755-6794

[9] NaIO4/KI/NaCl:: a new reagent system for iodination of activated aromatics through in situ generation of iodine monochloride [J].

Emmanuvel, Lourdusamy ;

Shukla, Ravi Kant ;

Sudalai, Arumugam ;

Gurunath, Suryavanshi ;

Sivaram, Swaminathan .

TETRAHEDRON LETTERS, 2006, 47 (28) :4793-4796

[10] MULTIPLY CONVERGENT SYNTHESES VIA CONJUGATE-ADDITION REACTIONS TO CYCLOALKENYL SULFONES [J].

FUCHS, PL ;

BRAISH, TF .

CHEMICAL REVIEWS, 1986, 86 (05) :903-917

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