Platinum-Catalyzed Oxoarylations of Ynamides with Nitrones

被引：61

作者：

Bhunia, Sabyasachi ^{[1
]}

Chang, Chin-Jung ^{[1
]}

Liu, Rai-Shung ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 21期

关键词：

GOLD CATALYSIS; 3+2 CYCLOADDITION; ALKYNES; CARBENOIDS; GENERATION; EPOXIDES; OXAZOLES; OXIDANTS; ALKENES; CASCADE;

D O I：

10.1021/ol302621z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new platinum-catalyzed oxoarylation of ynamides with nitrones is reported. Cascade sequences for the synthesis of indolin-2-ones via NaBH3CN reduction in situ of the initially formed oxoarylation products are also developed.

引用

页码：5522 / 5525

页数：4

共 33 条

[1] Gold(I)-Catalyzed Intermolecular Oxyarylation of Alkynes: Unexpected Regiochemistry in the Alkylatioin of Arenes [J].

Cuenca, Ana B. ;

Montserrat, Sergi ;

Hossain, Kabir M. ;

Mancha, Gisela ;

Lledos, Agusti ;

Medio-Simon, Mercedes ;

Ujaque, Gregori ;

Asensio, Gregorio .

ORGANIC LETTERS, 2009, 11 (21) :4906-4909

[2]

Dateer R. B., 2012, CHEM INT, V51, P113

[3] Gold-catalyzed synthesis of substituted 2-aminofurans via formal [4+1]-cycloadditions on 3-en-1-ynamides [J].

Dateer, Ramesh B. ;

Pati, Kamalkishore ;

Liu, Rai-Shung .

CHEMICAL COMMUNICATIONS, 2012, 48 (57) :7200-7202

[4] Gold-Catalyzed Intermolecular [4+2] and [2+2+2] Cycloadditions of Ynamides with Alkenes [J].

Dateer, Ramesh B. ;

Shaibu, Balagopal S. ;

Liu, Rai-Shung .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (01) :113-117

[5] Intermolecular and Selective Synthesis of 2,4,5-Trisubstituted Oxazoles by a Gold-Catalyzed Formal [3+2] Cycloaddition [J].

Davies, Paul W. ;

Cremonesi, Alex ;

Dumitrescu, Lidia .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (38) :8931-8935

[6] Site-specific introduction of gold-carbenoids by intermolecular oxidation of ynamides or ynol ethers [J].

Davies, Paul W. ;

Cremonesi, Alex ;

Martin, Nicolas .

CHEMICAL COMMUNICATIONS, 2011, 47 (01) :379-381

[7] Gold- or Platinum-Catalyzed Synthesis of Sulfur Heterocycles: Access to Sulfur Ylides without Using Sacrificial Functionality [J].

Davies, Paul W. ;

Albrecht, Sebastien J-C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (44) :8372-8375

[8] Ynamides: A Modern Functional Group for the New Millennium [J].

DeKorver, Kyle A. ;

Li, Hongyan ;

Lohse, Andrew G. ;

Hayashi, Ryuji ;

Lu, Zhenjie ;

Zhang, Yu ;

Hsung, Richard P. .

CHEMICAL REVIEWS, 2010, 110 (09) :5064-5106

[9] Ynamides: Versatile Tools in Organic Synthesis [J].

Evano, Gwilherm ;

Coste, Alexis ;

Jouvin, Kevin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (16) :2840-2859

[10] Gold catalysis:: Synthesis of 3-acylindenes from 2-alkynylaryl epoxides [J].

Hashmi, A. Stephen K. ;

Buehrle, Miriam ;

Salathe, Ralph ;

Bats, Jan W. .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (13) :2059-2064

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