Acyl Donors and Additives for the Biocatalytic Friedel-Crafts Acylation

被引：22

作者：

Schmidt, Nina G. ^{[1
,2
]}

Kroutil, Wolfgang ^{[2
]}

机构：

[1] ACIB GmbH, Petersgasse 14, A-8010 Graz, Austria

[2] Graz Univ, BioTechMed Graz, Dept Inst Chem Organ & Bioorgan Chem Inst, NAWI Graz, Heinrichstr 28, A-8010 Graz, Austria

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 39期

关键词：

Biocatalysis; Biotransformations; Friedel-Crafts acylation; C-C coupling; Phenol ketones; ASYMMETRIC-SYNTHESIS; 2,4-DIACETYLPHLOROGLUCINOL; DERIVATIVES; AGENTS;

D O I：

10.1002/ejoc.201701079

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Friedel-Crafts acylation is a broadly applied reaction that can be conducted using various types of catalyst. However, a biocatalytic alternative has only been reported recently. In this study, the scope of acetyl donors is described, showing that, in addition to vinyl acetate derivatives, phenyl esters are also suitable donors. Furthermore, it was found that various amines enhance the reaction, whereby the effect do not seem to be correlated to the pH but to the structure of the donor. For instance, 1,4-diazabicyclo[2.2.2]octane (DABCO) turned out to be a viable alternative to imidazole; however the former performed best at pH 9.85, whereas the latter performed best at pH 8.3.

引用

页码：5865 / 5871

页数：7

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[1] Biosynthesis of phloroglucinol [J].