布朗斯特酸催化生物可再生阿魏酸及其衍生物的串联去功能化为生物邻苯二酚。
Brønsted Acid Catalyzed Tandem Defunctionalization of Biorenewable Ferulic acid and Derivates into Bio-Catechol.
机构信息
Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020, Antwerp, Belgium.
Center for Molecular Modeling, Ghent University, Technologiepark 46, 9052, Zwijnaarde, Belgium.
出版信息
Angew Chem Int Ed Engl. 2020 Feb 17;59(8):3063-3068. doi: 10.1002/anie.201913023. Epub 2020 Jan 21.
An efficient conversion of biorenewable ferulic acid into bio-catechol has been developed. The transformation comprises two consecutive defunctionalizations of the substrate, that is, C-O (demethylation) and C-C (de-2-carboxyvinylation) bond cleavage, occurring in one step. The process only requires heating of ferulic acid with HCl (or H SO ) as catalyst in pressurized hot water (250 °C, 50 bar N ). The versatility is shown on a variety of other (biorenewable) substrates yielding up to 84 % di- (catechol, resorcinol, hydroquinone) and trihydroxybenzenes (pyrogallol, hydroxyquinol), in most cases just requiring simple extraction as work-up.
已开发出一种将生物可再生阿魏酸高效转化为生物邻苯二酚的方法。该转化包括底物的两个连续去功能化步骤，即 C-O（脱甲基）和 C-C（去 2-羧基乙烯基）键的裂解，在一步中发生。该过程仅需在加压热水（250°C，50 bar N）中加热阿魏酸与 HCl（或 H2SO4）作为催化剂。该方法在各种其他（生物可再生）底物上具有通用性，产率高达 84%的二羟基苯（邻苯二酚、间苯二酚、对苯二酚）和三羟基苯（焦儿茶酚、羟基喹啉），在大多数情况下仅需简单萃取作为后处理。
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