Photocatalyzed synthesis of isochromanones and isobenzofuranones under batch and flow conditions

Beilstein Journal of Organic Chemistry

Andrea Basso¹  Manuel Anselmo¹  Davide Comoretto¹  Lisa Moni¹  Renata Riva¹  Hossny Ismail¹ 

[1] Università degli Studi di Genova, Dipartimento di Chimica e Chimica Industriale, Via Dodecaneso 31, Genova, Italy;

关键词: flow chemistry;    heterocycles;    multicomponent reactions;    photocatalysis;    photo-Meerwein arylation–addition;   

DOI  :  10.3762/bjoc.13.143

来源: DOAJ

【 摘 要 】

Photocatalyzed reactions of 2-(alkoxycarbonyl)benzenediazonium tetrafluoroborates with various alkenes afforded isochromanones in good yields, according to a mechanism that was investigated. The advantage of using highly soluble esters rather than carboxylic acids as starting compounds became evident when the reactions were performed under flow conditions. On the other hand, when 2-vinylbenzoic acid derivatives were employed as reagents, isobenzofuranones were obtained together with unprecedented benzo[e][1,3]oxazepin-1(5H)-ones, with the latter derived from incorporation of the solvent (acetonitrile).

【 授权许可】

Unknown