Rhodium catalyzed reaction of internal alkynes with organoborons under CO atmosphere: a product tunable reaction

被引：27

作者：

Artok, Levent ^{[1
]}

Kus, Melih ^{[1
]}

Aksin-Artok, Oezge ^{[1
]}

Dege, Fatma Nurcan ^{[1
]}

Oezkilinc, Fatma Yelda ^{[1
]}

机构：

[1] Izmir Inst Technol, Fac Sci, Dept Chem, TR-35430 Izmir, Turkey

来源：

TETRAHEDRON | 2009年 / 65卷 / 45期

关键词：

Carbonylation; Rhodium catalysis; Organoborons; ARYLBORONIC ACIDS; CARBONYLATIVE CYCLIZATION; TERMINAL ALKYNES; ARYL IODIDES; ANNULATION; ARYLATION; EFFICIENT;

D O I：

10.1016/j.tet.2009.09.044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkynes react with organoborons under a CO atmosphere in the presence of a rhodium(I) catalyst to afford mainly 5-aryl-2(5H)-furanones, alpha,beta-unsaturated ketones, and indanones. The product selectivity can be tuned by modifying the reaction conditions. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：9125 / 9133

页数：9

共 29 条

[21] STRUCTURE-ACTIVITY RELATIONSHIP OF ESTROGENS - RECEPTOR AFFINITY AND ESTROGEN ANTAGONIST ACTIVITY OF CERTAIN (E)-1,2,3-TRIARYL-2-PROPEN-1-ONES AND (Z)-1,2,3-TRIARYL-2-PROPEN-1-ONES [J].

MITTAL, S ;

DURANI, S ;

KAPIL, RS .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (04) :492-497

[22] Palladium-catalyzed carbonylative cyclization of 1-iodo-2-alkenylbenzenes [J].

Negishi, E ;

Coperet, C ;

Ma, SM ;

Mita, T ;

Sugihara, T ;

Tour, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (25) :5904-5918

[23] PALLADIUM-CATALYZED CROSS-CARBONYLATION OF ARYL IODIDES AND 1-ARYL-2-ALKYN-1-ONES [J].

OKURO, K ;

FURUUNE, M ;

MIURA, M ;

NOMURA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17) :4754-4756

[24] Palladium-catalyzed carbonylation of o-iodophenols with allenes [J].

Okuro, K ;

Alper, H .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1566-1567

[25] FACILE ONE-STEP SYNTHESIS OF 3,5,5-TRISUBSTITUTED 2(5H)-FURANONES [J].

PADWA, A ;

DEHM, D .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (21) :3139-3141

[26] Synthesis of isoindolo[2,1-α]indoles by the palladium-catalyzed annulation of internal acetylenes [J].

Roesch, KR ;

Larock, RC .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (02) :412-420

[27] New synthesis of 1,4-diketones via rhodium-catalysed 1,4 carbonylative addition of arylboronic acids to α,β-unsaturated ketones [J].

Sauthier, M ;

Castanet, Y ;

Mortreux, A .

CHEMICAL COMMUNICATIONS, 2004, (13) :1520-1521

[28] Carbonylative 1,4-addition of potassium aryltrifluoroborates to vinyl ketones [J].

Sauthier, Mathieu ;

Lamotte, Nicolas ;

Dheur, Julien ;

Castanet, Yves ;

Mortreux, Andre .

NEW JOURNAL OF CHEMISTRY, 2009, 33 (05) :969-971

[29]

Vizer SA, 2004, TETRAHEDRON, V60, P5499, DOI 10.1016/j.tet.2004.04.046

← 1 2 3 →