Synthesis of indenes via palladium-catalyzed carboannulation of diethyl 2-(2-(1-alkynyl)phenyl)malonate and organic halides

被引：56

作者：

Guo, LN

Duan, XH

Bi, HP

Liu, XY

Liang, YM ^{[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：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 08期

关键词：

D O I：

10.1021/jo0601361

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly substituted indenes have been prepared in good yields by the palladium-catalyzed carboannulation of diethyl 2-(2(1-alkynyl)phenyl)malonate with aryl, benzylic, and alkenyl halides. The reaction conditions and the scope of the process were examined, and a possible mechanism is proposed.

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页码：3325 / 3327

页数：3

相关论文

共 29 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] THE PALLADIUM-CATALYZED SYNTHESIS OF 2,3,5-TRISUBSTITUTED FURANS FROM 2-PROPARGYL-1,3-DICARBONYL COMPOUNDS AND VINYLIC OR ARYL TRIFLATES OR HALIDES [J].

ARCADI, A ;

CACCHI, S ;

LAROCK, RC ;

MARINELLI, F .

TETRAHEDRON LETTERS, 1993, 34 (17) :2813-2816

[3]

BECKER CL, 1991, SYNLETT, P642

[4] Palladium-mediated three-component synthesis of furo[2,3-b]pyridones by one-pot coupling of 3-lodopyridones, alkynes, and organic halides [J].

Bossharth, E ;

Desbordes, P ;

Monteiro, N ;

Balme, G .

ORGANIC LETTERS, 2003, 5 (14) :2441-2444

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

Cacchi, S ;

Fabrizi, G .

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

[6] Heterocycles via cyclization of alkynes promoted by organopalladium complexes [J].

Cacchi, S .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :42-64

[7] Cobalt-catalyzed regioselective carbocyclization reaction of o-iodophenyl ketones and aldehydes with alkynes, acrylates, and acrylonitrile:: A facile route to indenols and indenes [J].

Chang, KJ ;

Rayabarapu, DK ;

Cheng, CH .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (14) :4781-4787

[8] Synthesis of 3,4-disubstituted isoquinolines via palladium-catalyzed cross-coupling of o-(1-alkynyl)benzaldimines and organic halides [J].

Dai, GX ;

Larock, RC .

ORGANIC LETTERS, 2001, 3 (25) :4035-4038

[9] Synthesis of 3,4-disubstituted isoquinolines via palladium-catalyzed cross-coupling of 2-(1-alkynyl)benzaldimines and organic halides [J].

Dai, GX ;

Larock, RC .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :920-928

[10] Palladium-catalyzed one-pot synthesis of highly substituted furans by a three-component annulation reaction [J].

Duan, XH ;

Liu, XY ;

Guo, LN ;

Liao, MC ;

Liu, WM ;

Liang, YM .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) :6980-6983