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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Main Authors:	Manuel Anselmo, Lisa Moni, Hossny Ismail, Davide Comoretto, Renata Riva, Andrea Basso
Format:	Article
Language:	English
Published:	Beilstein-Institut 2017-07-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	flow chemistry heterocycles multicomponent reactions photocatalysis photo-Meerwein arylation–addition
Online Access:	https://doi.org/10.3762/bjoc.13.143

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spelling	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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Photocatalyzed synthesis of isochromanones and isobenzofuranones under batch and flow conditions

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