2018
DOI: 10.1016/j.tetlet.2018.03.010
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Chemoselective ester/ether C–O cleavage of methyl anisates by aluminum triiodide

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Cited by 10 publications
(6 citation statements)
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“…Cleavage of methyl 2‐anisate ( 4 m ) by AlCl 3 ‐NaI for 1 hour at room temperature afforded methyl salicylate 5 m in 68% yield. The demethylation of 4 m is envisioned to proceed via the coordination of the carboxylate oxygen to the Lewis acid followed by anchimeric effect facilitated ether cleavage . 3‐Methoxyphenol ( 4 n ) gave resorcinol ( 5 n ) in 35% yield under current conditions.…”
Section: Resultsmentioning
confidence: 99%
“…Cleavage of methyl 2‐anisate ( 4 m ) by AlCl 3 ‐NaI for 1 hour at room temperature afforded methyl salicylate 5 m in 68% yield. The demethylation of 4 m is envisioned to proceed via the coordination of the carboxylate oxygen to the Lewis acid followed by anchimeric effect facilitated ether cleavage . 3‐Methoxyphenol ( 4 n ) gave resorcinol ( 5 n ) in 35% yield under current conditions.…”
Section: Resultsmentioning
confidence: 99%
“…Similarly, when methyl 2‐anisate ( 3x′ ) was exposed to the demethylation conditions, both the ether and ester C−O bonds were cleaved that afforded salicylic acid ( 4x′ ) in 90% yield (Table ). It should be noted that the deprotection efficiency is comparable to that using AlI 3 via the two‐stage process . Sterically hindered ethyl and isopropyl groups were also readily removed when catechol monoalkyl ethers 3 y and 3y′ were treated with the optimum conditions, giving catechol ( 4 j ) in 89% and 84% yield, respectively.…”
Section: Resultsmentioning
confidence: 94%
“…Since DMSO and DIC were used to scavenging HI for the protection of acid‐labile functional groups from side‐reactions, these additives were used only when needed. It should also be noted that heating is necessitated for the cleavage of typical aryl alkyl ethers by either aluminum oxide iodide or aluminum triiodide in the absence of neighboring group participation effect . Thus, the reactions were conducted in acetonitrile at 80 °C.…”
Section: Resultsmentioning
confidence: 96%
“…We envisioned that N -benzylacylsulfonamides might react with AlCl 3 in a different manner based on a previous observation that although both AlCl 3 and AlI 3 are efficient in cleaving ether , and ester C–O bonds, these two Lewis acids display complementary reactivities toward aryl and alkyl carboxylic esters . The chloride favors deacylation, whereas the iodide prefers to attack the alkyl chemoselectively .…”
Section: Resultsmentioning
confidence: 99%