Platinum- and gold-catalyzed hydrative carbocyclization of oxo diynes for one-pot synthesis of benzopyrones and bicyclic spiro ketones

被引：59

作者：

Das, Arindam ^{[1
]}

Chang, Hsu-Kai ^{[1
]}

Yang, Cheng-Hua ^{[1
]}

Liu, Rai-Shung ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 18期

关键词：

D O I：

10.1021/ol801601q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a one-pot synthesis of benzopyrones and tricyclic spiroketones from hydrative carbocyclization of oxodiyne substrates catalyzed by PtCl(2) and PPh(3)AuCl/AgOTf, respectively. The distinct carbocyclizations with Pt and Au catalysts stem from their altered regioselectivity in the oxo-assisted hydration of the neighboring alkyne carbons.

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收藏

页码：4061 / 4064

页数：4

相关论文

共 23 条

[1] AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes [J].

Asao, N ;

Takahashi, K ;

Lee, S ;

Kasahara, T ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12650-12651

[2] PtCl2-catalyzed hydrative cyclization of trialkyne functionalities to form bicyclic spiro ketones [J].

Chang, Hsu-Kai ;

Datta, Swarup ;

Das, Arindam ;

Odedra, Arjan ;

Liu, Rai-Shung .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (25) :4744-4747

[3] Ruthenium-catalyzed hydrative cyclization of 1,5-enynes [J].

Chen, YY ;

Ho, DM ;

Lee, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (35) :12184-12185

[4] Platinum-catalyzed chemoselectively hydrative dimerization of 2-alkynyl-1-acetylbenzenes for one-pot facile synthesis of chrysene derivatives [J].

Das, Arindam ;

Liao, Hsuan-Hung ;

Liu, Rai-Shung .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24) :9214-9218

[5] Heterocycles by PtCl2 catalyzed intramolecular carboalkoxylation or carboamination of alkynes [J].

Fürstner, A ;

Davies, PW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (43) :15024-15025

[6] Cyclobutenes by platinum-catalyzed cycloisomerization reactions of enynes [J].

Fürstner, A ;

Davies, PW ;

Gress, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (23) :8244-8245

[7] Silver versus gold catalysis in tandem reactions of carbonyl functions onto alkynes: A versatile access to furoquinoline and pyranoquinoline cores [J].

Godet, Thomas ;

Vaxelaire, Carine ;

Michel, Carine ;

Milet, Anne ;

Belmont, Philippe .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (19) :5632-5641

[8] Gold catalysis contra platinum catalysis in hydroarylation contra phenol synthesis [J].

Hashmi, A. Stephen K. ;

Kurpejovic, Elzen ;

Frey, Wolfgang ;

Bats, Jan W. .

TETRAHEDRON, 2007, 63 (26) :5879-5885

[9] Generation and reaction of metal-containing carbonyl ylides: Tandem [3+2]-cycloaddition-carbene insertion leading to novel polycyclic compounds [J].

Iwasawa, N ;

Shido, M ;

Kusama, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (24) :5814-5815

[10] Gold(I)-catalyzed conia-ene reaction of β-ketoesters with alkynes [J].

Kennedy-Smith, JJ ;

Staben, ST ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (14) :4526-4527