2019
DOI: 10.1016/j.jorganchem.2018.10.021
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One-pot α-ferrocenylalkylation of amines and alcohols with α-ferrocenyl substituted alcohols under acid-free conditions

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Cited by 9 publications
(3 citation statements)
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“…We have previously reported a convenient methodology for the ferrocenyl alkylation of alcohols, heterocyclic thiols, and amino acids with (α-ferrocenylalkyl) carbonates under mild acid-free conditions. [25][26][27][28] The application of this method not only allowed us to obtain ferrocenyl sydnone imines (Table 2) but also made it possible to solve the problem of the inertness of 4-mercaptosydnones in the alkylation reaction under the action of α-hydroxy derivatives of ferrocene. The target ferrocene-containing 4-thiosydnones 3 were obtained in moderate yields.…”
Section: Resultsmentioning
confidence: 99%
“…We have previously reported a convenient methodology for the ferrocenyl alkylation of alcohols, heterocyclic thiols, and amino acids with (α-ferrocenylalkyl) carbonates under mild acid-free conditions. [25][26][27][28] The application of this method not only allowed us to obtain ferrocenyl sydnone imines (Table 2) but also made it possible to solve the problem of the inertness of 4-mercaptosydnones in the alkylation reaction under the action of α-hydroxy derivatives of ferrocene. The target ferrocene-containing 4-thiosydnones 3 were obtained in moderate yields.…”
Section: Resultsmentioning
confidence: 99%
“…[25,26] Carbonates 2 spontaneously decompose under neutral conditions even at room temperature producing the αferrocenylcarbocation that interacts with the nucleophile (or pre-nucleophile) NuH furnishing the α-ferrocenylalkylation product 3 (Scheme 1). [25,26] Carbonates 2 spontaneously decompose under neutral conditions even at room temperature producing the αferrocenylcarbocation that interacts with the nucleophile (or pre-nucleophile) NuH furnishing the α-ferrocenylalkylation product 3 (Scheme 1).…”
Section: Resultsmentioning
confidence: 99%
“…Recent examples include the use of ferro cenyl carbonates for alkylation of various nucleophiles in neutral and basic media. [14][15][16] Nevertheless, α-ferrocenyl-substituted alcohols are currently the most common alkylating agents. This is primarily due to their stability, simple handling, and a wide range of methods for their preparation.…”
mentioning
confidence: 99%