2020
DOI: 10.1016/j.tetlet.2020.152459
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Synthesis of Pummerer’s ketone and its analogs by iodosobenzene-promoted oxidative phenolic coupling

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Cited by 10 publications
(13 citation statements)
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“…The oxidation of compound 5 performed at both pH 6 and pH 7 afforded 4a,9b-dihydro-1,7,8,9b-tetramethyl-3­(4 H )-dibenzofuranone 5a as the main reaction product, in addition to 2,2′-dihydroxy-5,5′-6,6′-tetramethyldiphenyl 5b , and the spirobenzo­[1,3]-dioxol trimer 5c (Scheme and Table , entries 1 and 2). The formation of compound 5c was unexpected . It showed a structure similar to compound II (Scheme , highlighted structure) previously isolated after anodic oxidation of 2,4-dimethylphenol .…”
Section: Resultssupporting
confidence: 79%
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“…The oxidation of compound 5 performed at both pH 6 and pH 7 afforded 4a,9b-dihydro-1,7,8,9b-tetramethyl-3­(4 H )-dibenzofuranone 5a as the main reaction product, in addition to 2,2′-dihydroxy-5,5′-6,6′-tetramethyldiphenyl 5b , and the spirobenzo­[1,3]-dioxol trimer 5c (Scheme and Table , entries 1 and 2). The formation of compound 5c was unexpected . It showed a structure similar to compound II (Scheme , highlighted structure) previously isolated after anodic oxidation of 2,4-dimethylphenol .…”
Section: Resultssupporting
confidence: 79%
“…Note that the reaction was ineffective in a dark reactor, under anaerobic conditions (argon atmosphere), and in the absence of HRP, as well as in the presence of alternative organic solvents lacking a tertiary C–H bond, such as petroleum ether or n -hexane (S3). Pummerer’s ketone 2 showed all the characteristic NMR signals expected for the tricyclic structure . In particular, the presence of the H-4 hydrogen signal at 4.71 ppm (multiplet) coupled with the adjacent CH 2 group (double doublet centered at 3.05 ppm) confirmed the closure of the central tetrahydrofuran ring.…”
Section: Resultsmentioning
confidence: 85%
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“…Yu’s group developed an iodosobenzene diacetate (PhI­(OAc) 2 ) mediated formal oxidative CC double bond cleavage and reassembly for the synthesis of oxazoline and isothiazoline derivatives with high regioselectivity (Scheme b) . Iodosylbenzene (PhIO), a unique and benign hypervalent iodine reagent, can achieve group-transfer reactions, cross-coupling reactions, and oxidative dearomatization of phenols . Additionally, PhIO can also serve as an oxygen source and transfer the oxygen atom to the metal center or the products, realizing epoxidation, 1,2-difunctionalization of olefins, α-oxidation of carbonyls, and C–H activation .…”
mentioning
confidence: 99%