“…The slightly lower yields of 3-acylated products are due to increased substitution at the 1-and 2-position (Table 3, entries 7-18). However, acylation of 4-or 5-haloindoles with aliphatic acid anhydrides produced 3-acylindoles in good yields (Table 3, entries [19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34]. In addition, N-acylated byproducts were slightly decreased in comparison with electron-rich indoles, but 2-acylindoles were obtained in small amounts (Table 3, entries [19][20][21][22][23][24][25][26][27][28][29].…”
Section: Resultsmentioning
confidence: 99%
“…Although metal triflates have been applied extensively in Friedel-Crafts acylation of aromatic compounds [24][25][26][27][28], there has been only one report on the use of indium triflate for the acylation of indoles [29]. However, in that case, excess reagent and NH-protection were required to obtain 3-acylated indoles in good yields.…”
A fast and green method is developed for regioselective acylation of indoles in the 3-position without the need for protection of the NH position. The method is based on Friedel-Crafts acylation using acid anhydrides. The method has been optimized, and Y(OTf)3 in catalytic amounts is found to be the best catalyst together with the commercially available ionic liquid [BMI]BF4 (1-butyl-3-methylimidazolium tetrafluoro-borate) as solvent. The reaction is completed in a very short time using monomode microwave irradiation. The catalyst can be reused up to four times without significant loss of activity. A range of substituted indoles are investigated as substrates, and thirteen new compounds have been synthesized.
“…The slightly lower yields of 3-acylated products are due to increased substitution at the 1-and 2-position (Table 3, entries 7-18). However, acylation of 4-or 5-haloindoles with aliphatic acid anhydrides produced 3-acylindoles in good yields (Table 3, entries [19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34]. In addition, N-acylated byproducts were slightly decreased in comparison with electron-rich indoles, but 2-acylindoles were obtained in small amounts (Table 3, entries [19][20][21][22][23][24][25][26][27][28][29].…”
Section: Resultsmentioning
confidence: 99%
“…Although metal triflates have been applied extensively in Friedel-Crafts acylation of aromatic compounds [24][25][26][27][28], there has been only one report on the use of indium triflate for the acylation of indoles [29]. However, in that case, excess reagent and NH-protection were required to obtain 3-acylated indoles in good yields.…”
A fast and green method is developed for regioselective acylation of indoles in the 3-position without the need for protection of the NH position. The method is based on Friedel-Crafts acylation using acid anhydrides. The method has been optimized, and Y(OTf)3 in catalytic amounts is found to be the best catalyst together with the commercially available ionic liquid [BMI]BF4 (1-butyl-3-methylimidazolium tetrafluoro-borate) as solvent. The reaction is completed in a very short time using monomode microwave irradiation. The catalyst can be reused up to four times without significant loss of activity. A range of substituted indoles are investigated as substrates, and thirteen new compounds have been synthesized.
“…In addition to the preceding reaction classes, waste heterogeneous catalysts are reported for epoxidation, 166 dehydration, 167 ethanolysis, 168 condensation 169 and acylation. 170 Pyrolysed waste tires were used to derive a support for chiral Mn-salen complexes for the asymmetric epoxidation of unfunctionalised olens. 166 This thermally stable microporous support had a surface area of 85 m 2 g À1 , but lost 3% of its Mn content due to leaching over three successive recycles.…”
Section: Miscellaneous Applicationsmentioning
confidence: 99%
“…A solid acid catalyst composed of y ash-supported scandium triate was showed superior activity than zeolite beta and La 3+ ion exchanged zeolite beta in the Friedel-Cras acylation of 2-methoxynaphthalene to form 2-acetyle-6-methoxynaphthalene, a naproxen precursor. 170 The authors suggested that the y ash catalyst could replace zeolite beta in industrial applications, such as the preparation of the anti-inammatory drug naproxen, due to its superior activity and selectivity. The y ash catalyst was shown to be active when reused in four reaction cycles, where conversion fell from 84 to 77%.…”
Sustainability has become a watchword and guiding principle for modern society, and with it a growing appreciation that anthropogenic ‘waste’, in all its manifold forms, can offer a valuable source of energy, construction materials, chemicals and high value functional products.
“…[5,[7][8][9][10] Metal triflates are efficient and green catalysts for Friedel-Crafts acylation. [11][12][13][14][15][16][17][18][19][20][21][22] Recently, metal-triflate-catalyzed Friedel-Crafts acylation with carboxylic acids as the acylating reagents has been studied extensively. [23][24][25][26][27] Although the intramolecular Friedel-Crafts acylation of carboxylic acids has been catalyzed by metal triflates with only 5-10 %c atalytic loading, the requirement for volatile organic solvents and long reactiont imes are current shortcomings.…”
Metal‐triflate‐catalyzed intramolecular Friedel–Crafts acylation of 3‐arylpropanoic and 4‐arylbutanoic acids in triflate‐anion ionic liquids under monomodal microwave irradiation is reported. The environmentally benign synthetic procedure allows the formation of cyclic ketones in good yields within a short reaction time. The catalytic metal triflate in triflate‐anion ionic liquids can be easily recovered and reused several times without significant loss of the catalytic performance.
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