Photocatalyzed synthesis of isochromanones and isobenzofuranones under batch and flow conditions
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 eviden...
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doaj-b91edf10ff264b13ab8ec0c0d69cc63b2021-02-02T00:48:49ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-07-011311456146210.3762/bjoc.13.1431860-5397-13-143Photocatalyzed synthesis of isochromanones and isobenzofuranones under batch and flow conditionsManuel Anselmo0Lisa Moni1Hossny Ismail2Davide Comoretto3Renata Riva4Andrea Basso5Università degli Studi di Genova, Dipartimento di Chimica e Chimica Industriale, Via Dodecaneso 31, Genova, ItalyUniversità degli Studi di Genova, Dipartimento di Chimica e Chimica Industriale, Via Dodecaneso 31, Genova, ItalyUniversità degli Studi di Genova, Dipartimento di Chimica e Chimica Industriale, Via Dodecaneso 31, Genova, ItalyUniversità degli Studi di Genova, Dipartimento di Chimica e Chimica Industriale, Via Dodecaneso 31, Genova, ItalyUniversità degli Studi di Genova, Dipartimento di Chimica e Chimica Industriale, Via Dodecaneso 31, Genova, ItalyUniversità degli Studi di Genova, Dipartimento di Chimica e Chimica Industriale, Via Dodecaneso 31, Genova, ItalyPhotocatalyzed 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).https://doi.org/10.3762/bjoc.13.143flow chemistryheterocyclesmulticomponent reactionsphotocatalysisphoto-Meerwein arylation–addition |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Manuel Anselmo Lisa Moni Hossny Ismail Davide Comoretto Renata Riva Andrea Basso |
spellingShingle |
Manuel Anselmo Lisa Moni Hossny Ismail Davide Comoretto Renata Riva Andrea Basso Photocatalyzed synthesis of isochromanones and isobenzofuranones under batch and flow conditions Beilstein Journal of Organic Chemistry flow chemistry heterocycles multicomponent reactions photocatalysis photo-Meerwein arylation–addition |
author_facet |
Manuel Anselmo Lisa Moni Hossny Ismail Davide Comoretto Renata Riva Andrea Basso |
author_sort |
Manuel Anselmo |
title |
Photocatalyzed synthesis of isochromanones and isobenzofuranones under batch and flow conditions |
title_short |
Photocatalyzed synthesis of isochromanones and isobenzofuranones under batch and flow conditions |
title_full |
Photocatalyzed synthesis of isochromanones and isobenzofuranones under batch and flow conditions |
title_fullStr |
Photocatalyzed synthesis of isochromanones and isobenzofuranones under batch and flow conditions |
title_full_unstemmed |
Photocatalyzed synthesis of isochromanones and isobenzofuranones under batch and flow conditions |
title_sort |
photocatalyzed synthesis of isochromanones and isobenzofuranones under batch and flow conditions |
publisher |
Beilstein-Institut |
series |
Beilstein Journal of Organic Chemistry |
issn |
1860-5397 |
publishDate |
2017-07-01 |
description |
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). |
topic |
flow chemistry heterocycles multicomponent reactions photocatalysis photo-Meerwein arylation–addition |
url |
https://doi.org/10.3762/bjoc.13.143 |
work_keys_str_mv |
AT manuelanselmo photocatalyzedsynthesisofisochromanonesandisobenzofuranonesunderbatchandflowconditions AT lisamoni photocatalyzedsynthesisofisochromanonesandisobenzofuranonesunderbatchandflowconditions AT hossnyismail photocatalyzedsynthesisofisochromanonesandisobenzofuranonesunderbatchandflowconditions AT davidecomoretto photocatalyzedsynthesisofisochromanonesandisobenzofuranonesunderbatchandflowconditions AT renatariva photocatalyzedsynthesisofisochromanonesandisobenzofuranonesunderbatchandflowconditions AT andreabasso photocatalyzedsynthesisofisochromanonesandisobenzofuranonesunderbatchandflowconditions |
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1724312930452766720 |