Electrocatalytic Dehydrogenative Esterification of Aliphatic Carboxylic Acids: Access to Bioactive Lactones

Electrocatalytic Dehydrogenative Esterification of Aliphatic Carboxylic Acids: Access to Bioactive Lactones

A scalable and efficient electrocatalytic dehydrogenative esterification is reported. With an indirect electrolysis strategy, both intra- and intermolecular-type reactions were amenable to this practical method. With n-Bu4NI as the catalyst, undesired decarboxylation and Baeyer–Villiger oxidation we...

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Veröffentlicht in:Organic letters 2017-12, Vol.19 (24), p.6622-6625
Hauptverfasser: Zhang, Sheng, Lian, Fei, Xue, Mengyu, Qin, Tengteng, Li, Lijun, Zhang, Xu, Xu, Kun
Format: Artikel
Sprache:eng
Schlagworte:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemical synthesis
Benzophenones - chemical synthesis
Carboxylic Acids - chemistry
Catalysis
Electrochemical Techniques
Esterification
Lactones - chemistry
Oxidation-Reduction
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Zusammenfassung:A scalable and efficient electrocatalytic dehydrogenative esterification is reported. With an indirect electrolysis strategy, both intra- and intermolecular-type reactions were amenable to this practical method. With n-Bu4NI as the catalyst, undesired decarboxylation and Baeyer–Villiger oxidation were suppressed. More importantly, this novel method provided reliable and direct access to the natural product cytosporanone A on a gram scale.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b03333