Biocatalytic Friedel–Crafts Acylation and Fries Reaction. (23rd May 2017)

• Record Type: Journal Article
• Authors: Schmidt, Nina G.; Pavkov‐Keller, Tea; Richter, Nina; Wiltschi, Birgit; Gruber, Karl; Kroutil, Wolfgang
• Is Part Of: Angewandte Chemie. Volume 129:Number 26(2017)
• Page Start: 7723
• Page End: 7727
• Publication Date: 2017-05-23
• Subjects: Acylierungen -- Arene -- Biokatalyse -- Enzyme -- Umlagerungen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201703270
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: The Friedel–Crafts acylation is commonly used for the synthesis of aryl ketones, and a biocatalytic version, which may benefit from the chemo‐ and regioselectivity of enzymes, has not yet been introduced. Described here is a bacterial acyltransferase which can catalyze Friedel–Crafts C‐acylation of phenolic substrates in buffer without the need of CoA‐activated reagents. Conversions reach up to >99 %, and various C‐ or O‐acyl donors, such as DAPG or isopropenyl acetate, are accepted by this enzyme. Furthermore the enzyme enables a Fries rearrangement‐like reaction of resorcinol derivatives. These findings open an avenue for the development of alternative and selective C−C bond formation methods.