Chemoselective generation of acyl phosphates, acylium ion equivalents, from carboxylic acids and an organophosphate ester in the presence of a Brønsted acid

We describe the chemoselective conversion of carboxylic acids to functional aromatic ketones promoted by a tailored organophosphate ester in the presence of a Brønsted acid. The protonated phosphate ester reacts with the carboxylic acid to form acyl phosphate, which reacts with benzenes to give arom...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2017, Vol.53 (9), p.1482-1485
Hauptverfasser: Sumita, Akinari, Otani, Yuko, Ohwada, Tomohiko
Format: Artikel
Sprache:eng
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Zusammenfassung:We describe the chemoselective conversion of carboxylic acids to functional aromatic ketones promoted by a tailored organophosphate ester in the presence of a Brønsted acid. The protonated phosphate ester reacts with the carboxylic acid to form acyl phosphate, which reacts with benzenes to give aromatic ketones, probably through the acylium ion or its equivalent. The reaction time is short even at room temperature, and the reaction is compatible with various other functional groups, including amines, olefins, esters, amides and nitriles.
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc09618b