2011
DOI: 10.1016/j.tetlet.2011.07.010
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Organic hydrogen phosphites and hydrogen phosphates catalyzed Friedel–Crafts amidoalkylation of indoles with aryl aldimines

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Cited by 14 publications
(5 citation statements)
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“…Diphenyl phosphate [(PhO) 2 P­(O)­OH, DPP] is widely used and can catalyze a variety of transformations such as Friedel–Crafts and Diels–Alder reactions , and ring-opening polymerizations . Its reactivity is limited due to its modest acidity but can be enhanced by the presence of strong electron-withdrawing groups on the two aromatic rings .…”
mentioning
confidence: 99%
See 1 more Smart Citation
“…Diphenyl phosphate [(PhO) 2 P­(O)­OH, DPP] is widely used and can catalyze a variety of transformations such as Friedel–Crafts and Diels–Alder reactions , and ring-opening polymerizations . Its reactivity is limited due to its modest acidity but can be enhanced by the presence of strong electron-withdrawing groups on the two aromatic rings .…”
mentioning
confidence: 99%
“…The presence of a phosphoryl oxygen also can serve as a hydrogen bond accepting site, enabling dual or bifunctional activation modes that increase their catalytic potential. 1,9a,10 Diphenyl phosphate [(PhO) 2 P(O)OH, DPP] is widely used and can catalyze a variety of transformations such as Friedel− Crafts and Diels−Alder reactions 11,12 and ring-opening polymerizations. 13 Its reactivity is limited due to its modest acidity but can be enhanced by the presence of strong electronwithdrawing groups on the two aromatic rings.…”
mentioning
confidence: 99%
“…Ongoing nucleophilic attack of indole on intermediate D with the help of the amino group of anthranilic acid and proton shuttle releases a bis-indole adduct. Notably, the amino group as the Brønsted base is necessary for C–C bond formation and proton shuttle of indoles . Owing to the synergistic effect of binary activations, further interaction of indoles with initial intermediates was promoted in the reactions.…”
Section: Results and Discussionmentioning
confidence: 99%
“…Notably, the amino group as the Brønsted base is necessary for C−C bond formation and proton shuttle of indoles. 40 Owing to the synergistic effect of binary activations, 41 further interaction of indoles with initial intermediates was promoted in the reactions. This cooperation of Ti Lewis acid and Brønsted base explains the selectivity in the double Friedel−Crafts reaction.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…Interest in phosphonate chemistry is owed to the applications they display [1,2] as well as their properties such as proton conductivity [3,4], optical [5] and catalyst properties [6]. A search of the Cambridge Structural Database (CSD version 5.40) [7] returned 61 different structures containing hydrogen phosphonate anion.…”
Section: Introductionmentioning
confidence: 99%