Synthesis of 2-substitued 3-aroylindenes via palladium-catalyzed carbonylative cyclization of diethyl 2-(2-(1-alkynyl)phenyl) malonates with aryl halides

被引：40

作者：

Duan, Xin-Hua

Guo, Li-Na

Bi, Hai-Peng

Liu, Xue-Yuan

Liang, Yong-Min ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Solid Lubricat, Lanzhou 730000, Peoples R China

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 14期

关键词：

3-SUBSTITUTED; 4-AROYLISOQUINOLINES; O-ALKYNYLPHENOLS; CARBOANNULATION; INDENES;

D O I：

10.1021/ol061019v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The palladium-catalyzed reaction of readily accessible diethyl 2-(2-(1-alkynyl) phenyl)malonates with aryl halides under a balloon pressure of CO produced 2-substitued 3-aroylindenes in good yields. The reaction is believed to proceed via cyclization of the alkyne containing a proximate nucleophilic center promoted by an acylpalladium complex.

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页码：3053 / 3056

页数：4

相关论文

共 20 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]

Arcadi A, 1999, EUR J ORG CHEM, V1999, P1137

[3] A palladium-catalyzed domino reaction of 3-acetyl-5-hexyn-2-one with aryl iodides under carbon monoxide [J].

Arcadi, A ;

Rossi, E .

TETRAHEDRON LETTERS, 1996, 37 (37) :6811-6814

[4] 2-SUBSTITUTED-3-ACYLINDOLES THROUGH THE PALLADIUM-CATALYZED CARBONYLATIVE CYCLIZATION OF 2-ALKYNYLTRIFLUOROACETANILIDES WITH ARYL HALIDES AND VINYL TRIFLATES [J].

ARCADI, A ;

CACCHI, S ;

CARNICELLI, V ;

MARINELLI, F .

TETRAHEDRON, 1994, 50 (02) :437-452

[5] Palladium-catalyzed reaction of o-ethynylphenols, o-((trimethylsilyl)ethynyl)phenyl acetates, and o-alkynylphenols with unsaturated triflates or halides: A route to 2-substituted-, 2,3-disubstituted-, and 2-substituted-3-acylbenzo[b]furans [J].

Arcadi, A ;

Cacchi, S ;

DelRosario, M ;

Fabrizi, G ;

Marinelli, F .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9280-9288

[6] Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].

Cacchi, S ;

Fabrizi, G .

CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920

[7]

Cacchi S, 1999, SYNLETT, P620

[8] Synthesis of 3-substituted 4-aroylisoquinolines via Pd-catalyzed carbonylative cyclization of o-(1-alkynyl)benzaldimines [J].

Dai, GX ;

Larock, RC .

ORGANIC LETTERS, 2002, 4 (02) :193-196

[9] Synthesis of 3-substituted 4-aroylisoquinolines via Pd-catalyzed carbonylative cyclization of 2-(1-alkynyl)benzaldimines [J].

Dai, GX ;

Larock, RC .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7042-7047

[10]

DILLARD RD, 1996, Patent No. 9603120