2011
DOI: 10.1016/j.tet.2011.04.065
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Electrochemical synthesis of dendritic diarylcarbenium ion pools

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Cited by 18 publications
(13 citation statements)
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“…A Friedel–Crafts-type alkylation [ 29 ] of diphenylsilane 3 with 2 in the presence of boron trifluoride etherate as a Lewis acid gave 4 in 86% yield. The oxidation potential of 4 ( E ox = 1.17 V vs SCE) is slightly lower than that of the fluorine analogue ( E ox = 1.25 V vs SCE) which was used as a precursor of the dendritic cation in our previous work [ 25 ], indicating that bromine analogue 4 can act as a precursor of the dendritic cation.…”
Section: Resultsmentioning
confidence: 91%
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“…A Friedel–Crafts-type alkylation [ 29 ] of diphenylsilane 3 with 2 in the presence of boron trifluoride etherate as a Lewis acid gave 4 in 86% yield. The oxidation potential of 4 ( E ox = 1.17 V vs SCE) is slightly lower than that of the fluorine analogue ( E ox = 1.25 V vs SCE) which was used as a precursor of the dendritic cation in our previous work [ 25 ], indicating that bromine analogue 4 can act as a precursor of the dendritic cation.…”
Section: Resultsmentioning
confidence: 91%
“…Low-temperature NMR analysis indicated that an accumulation of dendritic diarylcarbenium ion 6 in the solution had occurred. The chemical shift of the cationic carbon ( 13 C NMR δ 194.8) and that of the proton attached to the cationic carbon ( 1 H NMR δ 9.93) indicated that there was no interaction between the cationic carbon and peripheral bromo groups, because the chemical shifts were almost identical to those of the fluorine analogue ( 13 C NMR δ 194.4, 1 H NMR δ 9.92) [ 25 ].…”
Section: Resultsmentioning
confidence: 99%
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“…457 Diarylcarbenium ions can successfully be generated and accumulated by low-temperature electrochemical oxidation using the ''cation pool'' method. [458][459][460][461][462][463][464][465][466] In the presence of DMSO, alkoxysulfonium ions serve as the key intermediates. Treatment with a base, such as Et 3 N, or hydrolysis selectively affords the corresponding ketone 467 (Scheme 48) or alcohol 468 (Scheme 49).…”
Section: Electrochemical C-h Bond Oxygenationmentioning
confidence: 99%
“…For example, diarylcarbenium ion pools 1220 reacted with 1-(trimethylsilyl)-1,1-diphenylmethane and synthesis of dendrimers 21,22 and dendronized polymers 23 has been easily accomplished by repeating this reaction. This finding prompted us to examine multiple alkylation of oligothiophenes, 2426 which serve as electronically interesting structures, with simple and extended diarylcarbenium ions.…”
mentioning
confidence: 99%