Palladium-catalyzed carbonylative annulation reaction of 2-(1-alkynyl)benzenamines: Selective synthesis of 3-(Halomethylene)indolin-2-ones

被引：97

作者：

Tang, Shi

Yu, Quan-Fu

Peng, Peng

Li, Jin-Heng ^{[1
]}

Zhong, Ping

Tang, Ri-Yuan

机构：

[1] Wenzhou Univ, Coll Chem & Mat Sci, Wenzhou 325035, Peoples R China

[2] Hunan Normal Univ, Key Lab Chem Biol & Tradit Chinese Med Res, Changsha 410081, Peoples R China

[3] Chinese Acad Sci, Tech Inst Phys & Chem, Beijing 100101, Peoples R China

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 17期

关键词：

D O I：

10.1021/ol701450n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and selective palladium-catalyzed carbonylative annulation process for the synthesis of 3-(halomethylene)indolin-2-ones was demonstrated. In the presence of PdX2 and CuX2, 3-(halomethylene)indolin-2-ones were selectively obtained from the carbonylative annulations of 2-(1-alkynyl)benzenamines with CO in moderate to good yields.

引用

收藏

页码：3413 / 3416

页数：4

相关论文

共 39 条

[1] 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

[2]

ARCADI A, 1986, SYNTHESIS-STUTTGART, P749

[3]

BACKVALL JE, 1980, J AM CHEM SOC, V102, P393

[4] NEW INDOLE-DERIVATIVES - SYNTHESIS OF 3-ACYL-1-CARBETHOXY-2-TRIFLUOROMETHANESULFONYLINDOLES AND OF SUBSTITUTED 2-VINYLINDOLES [J].

BECCALLI, EM ;

MARCHESINI, A .

TETRAHEDRON, 1995, 51 (08) :2353-2362

[5]

BECCALLI EM, 1994, TETRAHEDRON, V50, P12697

[6] A tandem Heck-carbocyclization/Suzuki-coupling approach to the stereoselective syntheses of asymmetric 3,3-(diarylmethylene)indolinones [J].

Cheung, WS ;

Patch, RJ ;

Player, MR .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3741-3744

[7] Heck-Suzuki-Miyaura domino reactions involving ynamides.: An efficient access to 3-(Arylmethylene)isoindolinones [J].

Couty, S ;

Liégault, B ;

Meyer, C ;

Cossy, J .

ORGANIC LETTERS, 2004, 6 (15) :2511-2514

[8] A domino sequence consisting of insertion, coupling, isomerization, and Diels-Alder steps yields highly fluorescent spirocycles [J].

D'Souza, DM ;

Rominger, F ;

Müller, TJJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (01) :153-158

[9] The trans-chloropalladation reaction of propargyl amines and thioethers. X-ray crystal structure of trans-[Pd-trans-C(Ph)=C(Cl)CH(Me)S(i-Pr)(Cl)(Py)] [J].

Dupont, J ;

Basso, NR ;

Meneghetti, MR ;

Konrath, RA ;

Burrow, R ;

Horner, M .

ORGANOMETALLICS, 1997, 16 (11) :2386-2391

[10] Novel synthesis of oxindoles from carbamoyl chlorides via palladium catalysed cyclisation-anion capture [J].

Fielding, MR ;

Grigg, R ;

Urch, CJ .

CHEMICAL COMMUNICATIONS, 2000, (22) :2239-2240

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