Indium triflate-catalyzed coupling of indoles with acyl phosphonates: synthesis of bis(indolyl)methane phosphonates

Dasbasi, Teslima
Polat-Cakir, Sidika
Abdullah, Meysun
Demir, Ayhan Sıtkı
The coupling reaction of N-methylindole with alkyl and aryl phosphonate is described. The reaction works in the presence of 10 mol % of indium triflate and furnished bis(indolyl)methane phosphonates in good yield and high selectivity.


Hetero Diels-Alder reactions of acyl phosphonates: synthesis of glycosyl type phosphonates
Polat-Cakir, Sidika; Demir, Ayhan Sıtkı (Elsevier BV, 2011-04-01)
We have prepared glycosyl type phosphonates via hetero Diels-Alder (HDA) reactions of acyl phosphonates with electron rich dienes. HDA reactions of acyl phosphonates with Danishefsky's diene required thermal activation to yield the desired dihydropyranones in good yield (70-91%). The reactions with Brassard's diene involved Lewis acid promotion to yield the corresponding lactones, though in moderate yield (33-69%).
Manganese(III) acetate-mediated oxidative coupling of phenylhydrazines with furan and thiophene: a novel method for hetero biaryl coupling
Demir, Ayhan Sıtkı; Reis, O; Emrullahoglu, M (Elsevier BV, 2002-09-30)
A convenient new method for the arylation of furan and thiophene with arylhydrazine and manganese(III) acetate is described. Oxidation of arylhydrazines with Mn(III) acetate in furan or thiophene affords the corresponding 2-aryl-substituted furans and thiophenes in good yield using commercially available materials; access to 2-substituted heterobiaryls works selectively, and coupling occurs with loss of the hydrazine moiety.
Synthesis of ferrocenyl quinones
Zora, Metin; Acikalin, S (Elsevier BV, 2003-03-03)
A squarate-based synthesis of ferrocenyl quinones is described. Thermolysis of ferrocenyl-substituted cyclobutenones, prepared from ferrocenyl cyclobutenediones and alkenyllithiums, affords hydroquinones, which furnish, upon oxidation, ferrocenyl quinones. Ferrocenyl cyclobutenediones have been prepared from known cyclo butenediones by nucleophilic addition of ferrocenyllithium followed by hydrolysis, Pd/Cu-cocatalyzed cross-coupling with (tri-n-butylstannyl)ferrocene or Friedel-Crafts alkylation with ferro...
Regioselective alkylation of dianions of cyclic 1.3-diketones via their monodimethylhydrazones. Synthesis of C-4 substituted cyclic 1.3-diketones
Enders, Dieter; Demir, Ayhan Sıtkı (Elsevier BV, 1989-1)
Cyclic 1.3-diketones are transformed into the corresponding monodimethylhydrazones, which can be alkylated regioselectively at C-4 via dianions with various alkyl halides. The regioselective alkylation of cyclic 1.3-diketones 1, to 4-substituted derivatives 4 is described.
Highly efficient and selective olefination of acyl phosphonates with ethyl diazoacetate catalyzed by a cobalt(II) porphyrin complex
Erturk, Erkan; Demir, Ayhan Sıtkı (Elsevier BV, 2008-08-04)
The cobalt(II) porphyrin complex (CoTPP) was found to be an efficient catalyst for the Wittig type olefination of acyl phosphonates with ethyl diazoacetate (EDA) in the presence of triphenylphosphine (Ph(3)P). By using this one pot methodology under mild conditions, densely functionalized vinyl phosphonates were obtained in high yields and high E/Z selectivities in relatively short reaction times. A rather broad substrate spectrum and steric influence on the reaction rate were observed.
Citation Formats
T. Dasbasi, S. Polat-Cakir, M. Abdullah, and A. S. Demir, “Indium triflate-catalyzed coupling of indoles with acyl phosphonates: synthesis of bis(indolyl)methane phosphonates,” TETRAHEDRON, pp. 3355–3359, 2011, Accessed: 00, 2020. [Online]. Available: