Pt(IV)-catalyzed cyclization of arene-alkyne substrates via C-H bond functionalization

被引：150

作者：

Pastine, SJ ^{[1
]}

Youn, SW ^{[1
]}

Sames, D ^{[1
]}

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

TETRAHEDRON | 2003年 / 59卷 / 45期

关键词：

C-H fuctionalization; C-H activation; platinum(IV); hydroarylation; alkynes; chromenes; benzopyrans; RETRACTED ARTICLE. SEE; CATALYZED ADDITION; SYNTHETIC METHOD; AROMATIC IMINES; PG; 8364; ACTIVATION; CYCLOISOMERIZATION; OLEFINS; OMEGA-ARYL-1-ALKYNES; 2H-1-BENZOPYRANS;

D O I：

10.1016/j.tet.2003.05.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety. PtCl4 is compatible with both terminal and disubstituted alkynes, as well as with various functionalities on the arene ring, including methyl, methoxyl, hydroxyl, protected amine, and halide. (C) 2003 Elsevier Ltd. All rights reserved.

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页码：8859 / 8868

页数：10

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