Light-Induced Dealkylation of Benzamides in Aqueous Solution

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dc.contributor.authorCybularczyk-Cecotka, Martyna
dc.contributor.authorKamińska, Agnieszka
dc.contributor.authorJopek, Zuzanna
dc.contributor.authorGiedyk, Maciej
dc.contributor.organizationInstitute of Organic Chemistry, Polish Academy of Sciencesen
dc.date.accessioned2022-09-15T13:02:46Z
dc.date.available2022-09-15T13:02:46Z
dc.date.issued2022
dc.description.abstractThe N-dealkylation reactions of benzamides occur naturally in living organisms but chemical methods remain poorly developed. So far, light-induced variants of these processes have been restricted to amides containing secondary N-alkyl groups or required pre-functionalization of the starting material. Here, we present a direct, controllable N-dealkylation of tertiary and secondary benzamides possessing primary alkyl substituents at N-atom. The developed strategy operates in aqueous environment under mild conditions involving either blue LEDs or sunlight irradiation. Preliminary mechanistic studies indicate two-step oxidation and the intermediacy of radicals at α-position to N-atom. Selectivity in N-dealkylation of homo- and heterosubstituted tertiary benzamides is also investigated.en
dc.description.sponsorshipNational Science Centre, Poland (SONATA 2018/31/D/ST5/00306)
dc.identifier.citationEur. J. Org. Chem. 2022, e202200913 ; https://doi.org/10.1002/ejoc.202200913en
dc.identifier.issn1434-193X
dc.identifier.issn1099-0690
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/21647
dc.language.isoen
dc.publisherWileyen
dc.rightsDozwolony użytek*
dc.subjectdealkylationen
dc.subjectbenzamidesen
dc.subjectphotochemistryen
dc.subjectaqueous solutionsen
dc.subjectlight-induceden
dc.titleLight-Induced Dealkylation of Benzamides in Aqueous Solutionen
dc.typearticleen
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