Synthesis of 2,5-Disubstituted 3-Iodofurans via Palladium-Catalyzed Coupling and Iodocyclization of Terminal Alkynes

被引：73

作者：

Chen, Zhengwang ^{[1
]}

Huang, Gao ^{[1
]}

Jiang, Huanfeng ^{[1
]}

Huang, Huawen ^{[1
]}

Pan, Xiaoyan ^{[1
]}

机构：

[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 04期

基金：

中国国家自然科学基金;

关键词：

HIGHLY SUBSTITUTED FURANS; FUNCTIONALIZED CONJUGATED ENYNES; RING-OPENING CYCLOISOMERIZATION; ELECTRON-DEFICIENT ALKYNES; POT CYCLIZATION REACTION; C BOND FORMATION; POLYSUBSTITUTED FURANS; EFFICIENT SYNTHESIS; TETRASUBSTITUTED FURANS; DOMINO PROCESS;

D O I：

10.1021/jo1023987

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,5-Disubstituted 3-iodofurans are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of (Z)-beta-bromoenol acetates and terminal alkynes, followed by iodocyclization. The useful intermediates conjugated enyne acetates are obtained in high yields in the transformation. Aryl- and alkyl-substituted alkynes undergo iodocyclization in good yields. The resulting iodine-containing furans can be readily elaborated to 2,3,5-trisubstituted furans.

引用

页码：1134 / 1139

页数：6

共 110 条

[1] 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

[2] An Extremely Facile Synthesis of Furans, Pyrroles, and Thiophenes by the Dehydrative Cyclization of Propargyl Alcohols [J].

Aponick, Aaron ;

Li, Chuan-Ying ;

Malinge, Jeremy ;

Marques, Emerson Finco .

ORGANIC LETTERS, 2009, 11 (20) :4624-4627

[3] 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

[4] Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols [J].

Arimitsu, Satoru ;

Jacobsen, Jesse M. ;

Hammond, Gerald B. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (07) :2886-2889

[5] Selective synthesis of fluorinated furan derivatives via AgNO3-catalyzed activation of an electronically deficient triple bond [J].

Arimitsu, Satoru ;

Hammond, Gerald B. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8559-8561

[6] Synthesis of trisubstituted furans from epoxypropargyl esters by sequential SmI2-promoted reduction-elimination and Pd(II)-catalyzed cycloisomerization [J].

Aurrecoechea, JM ;

Pérez, E ;

Solay, M .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (02) :564-569

[7] Palladium-catalyzed cyclization/Heck- and cyclization/conjugate-addition-type sequences in the preparation of polysubstituted furans [J].

Aurrecoechea, Jose M. ;

Durana, Aritz ;

Perez, Elena .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) :3650-3653

[8] Intramolecular iodoarylation reaction of alkynes:: easy access to derivatives of benzofused heterocycles [J].

Barluenga, J ;

Trincado, M ;

Marco-Arias, M ;

Ballesteros, A ;

Rubio, E ;

González, JM .

CHEMICAL COMMUNICATIONS, 2005, (15) :2008-2010

[9] 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

[10] Cyclization of carbonyl groups onto alkynes upon reaction with IPy2BF4 and their trapping with nucleophiles:: A versatile trigger for assembling oxygen heterocycles [J].

Barluenga, J ;

Vázquez-Villa, H ;

Ballesteros, A ;

González, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (30) :9028-9029

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