2022
DOI: 10.1021/acs.joc.2c01334
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Rh(III)-Catalyzed Oxidative Domino C–H/N–H Annulation: Diarylureas as Arylamine Donors for the Assembly of Indolo[2,1-a]isoquinolines

Abstract: An efficient and convenient Rh(III)-catalyzed double aryl C(sp2)−H bond and N−H activation and annulation reaction is reported for the synthesis of indolo[2,1-a]isoquinolines in the presence of the Cu(OAc) 2 oxidant under heating conditions. Distinct from previous works with other arylamine donors, one molecule of 1,3-diarylurea can serve as a precursor of two molecules of arylamine in the reaction with diaryl-substituted alkynes.

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Cited by 7 publications
(2 citation statements)
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“…Since the reaction could be restrained by 2,2,6,6-tetramethylpiperidoxyl (TEMPO), it is supposed to be a free radical reaction (Table 1, entry 8). 17 Salicylic acid trapping experiment further confirmed that the hydroxyl radical was involved in the process (Fig. S1 in ESI†).…”
Section: Resultsmentioning
confidence: 64%
“…Since the reaction could be restrained by 2,2,6,6-tetramethylpiperidoxyl (TEMPO), it is supposed to be a free radical reaction (Table 1, entry 8). 17 Salicylic acid trapping experiment further confirmed that the hydroxyl radical was involved in the process (Fig. S1 in ESI†).…”
Section: Resultsmentioning
confidence: 64%
“…Thus, it could be concluded that the photocatalytic process might occur through a free radical reaction mechanism. 18…”
Section: Resultsmentioning
confidence: 99%