2008
DOI: 10.1016/j.tetlet.2008.01.002
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Formate ester synthesis via reaction of 2-bromoethylamines with dimethylformamide

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Cited by 16 publications
(8 citation statements)
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“…Phenylacetaldehyde could arise from a pathway similar to the Bouveault reaction, whereby an aldehyde is formed from the reaction of a Grignard reagent and an N,N-disubstituted formamide. 79 The 12 C benzyl formate could originate from a Vilsmeier intermediate that becomes hydrolyzed during workup, 80 while the 13 C benzyl formate could arise from a nucleophilic attack by a formate anion, itself a product of CO 2 reduction at the cathode. The 13 C N,N-dimethylbenzylcarbamate could result from a nucleophilic attack by a carbamate anion, itself formed by CO 2 reacting with dimethylamine; the dimethylamine could be present from DMF decomposition.…”
Section: Comparison To Sacricial-anode Carboxylationmentioning
confidence: 99%
“…Phenylacetaldehyde could arise from a pathway similar to the Bouveault reaction, whereby an aldehyde is formed from the reaction of a Grignard reagent and an N,N-disubstituted formamide. 79 The 12 C benzyl formate could originate from a Vilsmeier intermediate that becomes hydrolyzed during workup, 80 while the 13 C benzyl formate could arise from a nucleophilic attack by a formate anion, itself a product of CO 2 reduction at the cathode. The 13 C N,N-dimethylbenzylcarbamate could result from a nucleophilic attack by a carbamate anion, itself formed by CO 2 reacting with dimethylamine; the dimethylamine could be present from DMF decomposition.…”
Section: Comparison To Sacricial-anode Carboxylationmentioning
confidence: 99%
“…Employing 1.0, 2.0 and 3.0 equivalents of PBr 3 to the reaction increased the yields of 4 to 84, 88, and 96%, respectively (entries [4][5][6]. In these cases, a trace amount of hydrolyzed product 5 was observed.…”
Section: Resultsmentioning
confidence: 96%
“…Table 1 When N-phenylacetamide 2 possessing an α-bromo group served as the starting material, the reaction gave the desired 4 in lower yield (73%, entry 8 in Table 1) compared to that of 1 bearing an α-chloro group (96%, entry 6). Unlike the use of 1 that the major substance in the reaction other 4 was the un-reacted 1 (entries [1][2][3][4], the major by-product was aniline resulted from the cleavage of C-N bond when 2 was used. Use of compound 3 possessing an α-iodo group as the starting material worsened the reaction, only provided the desired 4 in 9.0% yield and aniline had become the major product.…”
Section: Resultsmentioning
confidence: 99%
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“…[2] A more compelling alternative method for the synthesis of formate ester derivatives is via an O-alkylation of amides with alkyl halides. [3] Reports that exploit dimethylformamide (DMF) as a formate anion equivalent in the synthesis of formate ester have also been revealed. [4] CuCN is a widely renowned transition-metal cyanide in organometallic chemistry that has valuable synthetic capabilities [5] and a cascade of catalytic activities.…”
Section: Introductionmentioning
confidence: 99%