Synthesis of alkynyl and vinyl selenides via selenodecarboxylation of arylpropiolic and cinnamic acids

被引：61

作者：

Das, JP ^{[1
]}

Roy, UK ^{[1
]}

Roy, S ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Organomet & Catalysis Lab, Kharagpur 721302, W Bengal, India

来源：

ORGANOMETALLICS | 2005年 / 24卷 / 25期

关键词：

D O I：

10.1021/om050504b

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The selenodecarboxylation of phenylpropiolic and cinnamic acid derivatives with diorgano diselenide is promoted by iodosobenzene diacetate (PhI(OAc)(2), IBDA) in acetonitrile at 30-60 degrees C, leading to the formation of alkynyl selenides and vinyl selenides in moderate to excellent yields. Similar reactivity is also shown by iodosylbenzene (PhIO, IB). The reaction is also triggered in the solid state. An electrophilic mechanism is proposed for the transformation.

引用

页码：6136 / 6140

页数：5

共 77 条

[1] Hydroalumination and bromination of 1-(phenylselenyl)-1-alkynes [J].

Al-Hassan, MI .

SYNTHETIC COMMUNICATIONS, 2001, 31 (19) :3027-3030

[2] Palladium and platinum catalyzed hydroselenation of alkynes: Se-H vs Se-Se addition to CC bond [J].

Ananikov, VP ;

Malyshev, DA ;

Beletskaya, IP ;

Aleksandrov, GG ;

Eremenko, IL .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 679 (02) :162-172

[3] Skeletal rearrangements of bicyclo[2.2.2]lactones:: a short and efficient route towards Corey's lactone [J].

Augustyns, B ;

Maulide, N ;

Markó, IE .

TETRAHEDRON LETTERS, 2005, 46 (22) :3895-3899

[4] Cycloaddition reactions of 1-phenylseleno-2-(p-toluenesulfonyl)ethyne [J].

Back, TG ;

Bethell, RJ ;

Parvez, M ;

Taylor, JA ;

Wehrli, D .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20) :7426-7432

[5]

BACK TG, 1999, ORGANOSELENIUM CHEM, pCH9

[6] CONCISE SYNTHESES OF L-SELENOMETHIONINE AND OF L-SELENOCYSTINE USING RADICAL CHAIN-REACTIONS [J].

BARTON, DHR ;

BRIDON, D ;

HERVE, Y ;

POTIER, P ;

THIERRY, J ;

ZARD, SZ .

TETRAHEDRON, 1986, 42 (18) :4983-4990

[7] NEW DECARBOXYLATIVE CHALCOGENATION OF ALIPHATIC AND ALICYCLIC CARBOXYLIC-ACIDS [J].

BARTON, DHR ;

BRIDON, D ;

ZARD, SZ .

TETRAHEDRON LETTERS, 1984, 25 (50) :5777-5780

[8] STEREOSPECIFIC SYNTHESIS OF (-)-CARBOCYCLIC 2',3'-DIDEOXYTHYMIDINE, A POTENTIAL ANTI-AIDS AGENT [J].

BERES, J ;

SAGI, G ;

TOMOSKOZI, I ;

GRUBER, L ;

GULACSI, E ;

OTVOS, L .

TETRAHEDRON LETTERS, 1988, 29 (22) :2681-2684

[9] Organoselenium-based entry into versatile, α-(2-tributylstannyl)vinyl amino acids in scalemic form:: A new route to vinyl stannanes [J].

Berkowitz, DB ;

McFadden, JM ;

Chisowa, E ;

Semerad, CL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (44) :11031-11032

[10] Stereocontrolled synthesis of quaternary β,γ-unsaturated amino acids:: chain extension of D- and L-α-(2-tributylstannyl)vinyl amino acids [J].

Berkowitz, DB ;

Chisowa, E ;

McFadden, JM .

TETRAHEDRON, 2001, 57 (30) :6329-6343

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