Butyltellurium tribromide: A suitable electrophilic source to cyclization reactions

被引：13

作者：

Alves, Diego ^{[1
]}

Prigol, Marina ^{[1
]}

Nogueira, Cristina W. ^{[1
]}

Zeni, Gilson ^{[1
]}

机构：

[1] Univ Fed Santa Maria, CCNE, Lab Sintese, BR-97105900 Santa Maria, RS, Brazil

来源：

SYNLETT | 2008年 / 06期

关键词：

tellurium; electrophilic cyclization; chalcogenophenes;

D O I：

10.1055/s-2008-1042926

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We present here our results of the electrophilic cyclization reaction of (Z)-chalcogenoenynes using butyltellurium tribromide as an electrophilic source. The cyclization reaction proceeded cleanly under mild reaction conditions and 3-(butyltellanyl)chalcogenophenes were formed in moderate to excellent yields. Subsequent, using these heterocycles as substrate to palladium-catalyzed cross-coupling reactions a new carbon-carbon bond was formed in good yields.

引用

页码：914 / 918

页数：5

共 36 条

[1] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159

[2] Electrophilic cyclization of (Z)-selenoenynes:: Synthesis and reactivity of 3-iodoselenophenes [J].

Alves, Diego ;

Luchese, Cristiane ;

Nogueira, Cristina W. ;

Zeni, Gilson .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (18) :6726-6734

[3] A new approach to 2,3-disubstituted benzo[b]furans from o-alkynylphenols via 5-endo-dig-iodocyclisation/palladium-catalysed reactions [J].

Arcadi, A ;

Cacchi, S ;

Fabrizi, G ;

Marinelli, F ;

Moro, L .

SYNLETT, 1999, (09) :1432-1434

[4] Electrophilic cyclization of o-acetoxy- and o-benzyloxyalkynylpyridines:: An easy entry into 2,3-disubstituted furopyridines [J].

Arcadi, A ;

Cacchi, S ;

Di Giuseppe, S ;

Fabrizi, G ;

Marinelli, F .

ORGANIC LETTERS, 2002, 4 (14) :2409-2412

[5] Palladium-catalyzed cross-coupling reaction of 3-iodoselenophenes with boronic acids [J].

Barancelli, Daniela A. ;

Alves, Diego ;

Prediger, Patricia ;

Stangherlin, Eluza C. ;

Nogueira, Cristina W. ;

Zeni, Gilson .

SYNLETT, 2008, (01) :119-125

[6] IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes:: Direct assembly of 3-iodoindole cores [J].

Barluenga, J ;

Trincado, M ;

Rubio, E ;

González, JM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (21) :2406-2409

[7] Suzuki-Miyaura cross-coupling reactions of aryl tellurides with potassium aryltrifluoroborate salts [J].

Cella, R ;

Cunha, RLOR ;

Reis, AES ;

Pimenta, DC ;

Klitzke, CF ;

Stefani, HA .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :244-250

[8] The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4 [J].

Flynn, BL ;

Flynn, GP ;

Hamel, E ;

Jung, MK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (17) :2341-2343

[9] Iodine-induced reaction cascades for the rapid construction of variously substituted benzothiophenes [J].

Hessian, KO ;

Flynn, BL .

ORGANIC LETTERS, 2003, 5 (23) :4377-4380

[10] Synthesis of substituted isoquinolines by electrophilic cyclization of iminoalkynes [J].

Huang, QH ;

Hunter, JA ;

Larock, RC .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (10) :3437-3444

← 1 2 3 4 →