Programmed Synthesis of Tetraarylthiophenes through Sequential C-H Arylation

被引：211

作者：

Yanagisawa, Shuichi ^{[1
]}

Ueda, Kirika ^{[1
]}

Sekizawa, Hiromi ^{[1
]}

Itami, Kenichiro ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Sci, Dept Chem, Nagoya, Aichi 4648602, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 41期

关键词：

PALLADIUM-CATALYZED ARYLATION; CROSS-COUPLING REACTIONS; HETEROAROMATIC-COMPOUNDS; BOND FORMATION; FUNCTIONALIZATION; THIOPHENES; ACIDS; HETEROARENES; DERIVATIVES; ACTIVATION;

D O I：

10.1021/ja906215b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general protocol for the programmed synthesis of tetraarylthiophenes has been established. The utilization of three catalysts, RhCl(CO){P[OCH(CF3)(2)](3)}(2), PdCl2/P[OCH(CF3)(2)](3), and PdCl2/bipy, enables regioselective sequential arylations at the three C-H bonds of 3-methoxythiophene with iodoarenes. Interesting metal- and ligand-controlled regiodivergent: C-H arylations have been uncovered during this study. The installation of fourth aryl groups to the thus-generated 2,4,5-triaryl-3-methoxythiophenes has been accomplished through a sequence of demethylation, triflation, and Suzuki-Miyaura coupling.

引用

页码：14622 / +

页数：3

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