Microwave-irradiated transition-metal catalysis: Rapid and efficient dehydrative carbon-carbon coupling of alcohols with active methylenes

被引：29

作者：

Babu, Srinivasarao Arulananda ^{[1
,2
]}

Yasuda, Makoto ^{[1
,2
]}

Tsukahara, Yasunori ^{[2
]}

Yamauchi, Tomohisa ^{[2
]}

Wada, Yuji ^{[2
,3
]}

Baba, Akio ^{[1
,2
]}

机构：

[1] Osaka Univ, Dept Appl Chem, Suita, Osaka 5650871, Japan

[2] Osaka Univ, Grad Sch Engn, Suita, Osaka 5650871, Japan

[3] Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan

来源：

SYNTHESIS-STUTTGART | 2008年 / 11卷 / 11期

关键词：

alcohols; alkylations; catalysis; C-C Coupling; dicarbonyl compounds; microwave irradiation; transition metals;

D O I：

10.1055/s-2008-1067020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rapid and highly productive synthetic microwave-irradiation protocol for transition-metal-catalyzed carbon-carbon coupling of a wide range of benzylic/allylic alcohols with beta-diones, beta-keto esters, and dialkyl malonates is reported. In a representative screening of transition-metal catalysts, salts of Zn, Cu, Fe, Sc, Ru, Pt, Ta, and Mo were found to furnish the coupling products. In light of the results obtained, among all of these catalysts copper(II) triflate was found to be relatively more effective compared to other catalysts even in the case of a less reactive benzyl alcohol or diester. Interestingly, these MW-irradiated reactions are performed in a more or less MW-transparent medium, such as toluene, having a very low tan delta, or under neat conditions.

引用

页码：1717 / 1724

页数：8

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