Oxindole synthesis through intramolecular nucleophilic addition of vinylpalladiums to aryl isocyanates

被引：71

作者：

Kamijo, S

Sasaki, Y

Kanazawa, C

Schüsseler, T

Yamamoto, Y

机构：

[1] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA

[2] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 47期

关键词：

alkynes; isocyanates; nucleophilic addition; oxindoles; palladium;

D O I：

10.1002/anie.200502252

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Ringing the changes for organopalladium catalysts. A new nucleophilic reactivity of organopalladium species has been revealed. The reaction between aryl isocyanates and terminal alkynes in the presence of a palladium catalyst produces oxindoles through the intramolecular vinylpalladation of isocyanates (see scheme; dppe = 1,2-bis(diphenylphosphanyl) ethane). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

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收藏

页码：7718 / 7721

页数：4

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[31] Intramolecular nucleophilic addition of aryl bromides to ketones catalyzed by palladium [J].

Quan, LG ;

Lamrani, M ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (19) :4827-4828

[32]

Ready J. M., 2004, ANGEW CHEM, V116, P1290

[33] A mild and efficient synthesis of oxindoles: Progress towards the synthesis of welwitindolinone a isonitrile [J].

Ready, JM ;

Reisman, SE ;

Hirata, M ;

Weiss, MM ;

Tamaki, K ;

Ovaska, TV ;

Wood, JL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (10) :1270-1272

[34] Can agostic interaction affect regiochemistry of carbopalladation? Reverse regioselectivity in the palladium-catalyzed dimerization of aryl acetylenes [J].

Rubina, M ;

Gevorgyan, V .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :11107-11108

[35] Pincer complex-catalyzed allylation of aldehyde and imine substrates via nucleophilic η1-allyl palladium intermediates [J].

Solin, N ;

Kjellgren, J ;

Szabó, KJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (22) :7026-7033

[36] Indole synthesis via palladium-catalyzed intramolecular cyclization of alkynes and imines [J].

Takeda, A ;

Kamijo, S ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (23) :5662-5663

[37]

Tamaru Y., 2002, HDB ORGANOPALLADIUM, V2, P1917

[38] Carbopalladation of nitriles: Synthesis of 3,4-disubstituted 2-aminonaphthalenes and 1,3-benzoxazine derivatives by the palladium-catalyzed annulation of alkynes by (2-iodophenyl)acetonitrile [J].

Tian, QP ;

Pletnev, AA ;

Larock, RC .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :339-347

[39] THE ATOM ECONOMY - A SEARCH FOR SYNTHETIC EFFICIENCY [J].

TROST, BM .

SCIENCE, 1991, 254 (5037) :1471-1477

[40] METAL-MEDIATED APPROACH TO ENYNES [J].

TROST, BM ;

CHAN, C ;

RUHTER, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3486-3487

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