- The cooperative effect of Lewis pairs in the Friedel-Crafts hydroxyalkylation reaction: A simple and effective route for the synthesis of (±)-carbinoxamine
-
An efficient C-C bond formation strategy between aromatic/heteroaromatic π-nucleophiles and Lewis acid activated aldehydes is described. This aromatic electrophilic substitution reaction of arenes or heteroarenes is facilitated by Lewis acid AlBr3. Aromatic rings with electron donating substituents are excellent nucleophilic counterparts in this reaction, generating carbinols in excellent yields (61-94%). The formation of triarylmethanes is also witnessed in the case of certain reactive aldehydes and aromatic π-nucleophiles through reactive carbocation formation. The formation of triarylmethane is reduced to a greater extent via retardation of the second π-nucleophile addition through a Lewis base, for example, pyridine, coordination with an aluminium alkoxide intermediate. Various aliphatic aldehydes also underwent Friedel-Crafts type hydroxyalkylation and generated the expected carbinols in moderate yields (41-53%) in the presence of AlBr3. This protocol has been successfully applied to the synthesize of the (±)-carbinoxamine, a therapeutically important histamine H1 antagonist, in a one-pot manner.
- Harikrishnan, Adhikesavan,Sanjeevi, Jayakumar,Ramanathan, Chinnasamy Ramaraj
-
p. 3633 - 3647
(2015/03/30)
-
- Friedel-Crafts hydroxyalkylation through activation of a carbonyl group using AlBr3: An easy access to pyridyl aryl/heteroaryl carbinols
-
Aromatic electrophilic substitution of aromatic/electron rich heteroaromatic compounds with AlBr3 activated aldehydes/ketone to afford pyridyl aryl/heteroaryl or diaryl carbinols is described. The strong electron donating group dictates the regiochemical outcome of the product.
- Harikrishnan, Adhikesavan,Selvakumar, Jayaraman,Gnanamani, Elumalai,Bhattacharya, Suman,Ramanathan, Chinnasamy Ramaraj
-
supporting information
p. 563 - 567
(2013/04/10)
-
- Room-temperature bismuth-catalyzed bis-arylation of carbonyl compounds with aryl ethers and phenols
-
Using Bi2(SO4)3 as the catalyst and TMSCl as the additive, a wide variety of aldehydes, ketones, and acetals were smoothly condensed with aryl ethers at room temperature to provide the corresponding diarylmethanes and triarylmethanes selectively in good to excellent yields. Using Bi2(SO4)3 as the catalyst and TMSCl as the additive, a wide variety of aldehydes, ketones, and acetals were smoothly condensed with aryl ethers at room temperature to selectively provide the corresponding diarylmethanes and triarylmethanes in good to excellent yields. Copyright
- Liu, Congrong,Li, Manbo
-
p. 1274 - 1278
(2013/11/06)
-
- Facile and green synthesis of triarylmethanes using silica sulfuric acid as a reusable catalyst under solvent-free conditions
-
A facile and environmentally-benign protocol has been developed for the synthesis of triarylmethanes (TAMs) from the reaction of different arenes and aldehydes in the presence of silica sulfuric acid (SSA) as a heterogeneous and reusable catalyst under solvent-free conditions. Easy work-up, short reaction times, high yields, high selectivity, mild and green conditions are other salient features of this method.
- Mohammadpoor-Baltork,Moghadam,Tangestaninejad,Mirkhani,Mohammadiannejad-Abbasabadi,Zolfigol
-
experimental part
p. 934 - 943
(2012/04/17)
-
- Preparation of triaryl- and triheteroarylmethanes under ytterbium triflate catalysis and solvent-free conditions
-
Triaryl- and triheteroarylmethanes have been synthesized in very good yield under solvent-free conditions from differently substituted aldehydes and 2-methylfuran or methoxybenzene in the presence of Yb(OTf)3 as catalyst. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
- Genovese, Salvatore,Epifano, Francesco,Pelucchini, Caroline,Curini, Massimo
-
experimental part
p. 1132 - 1135
(2009/06/18)
-
- Catalytic selective bis-arylation of imines with anisole, phenol, thioanisole and analogues
-
The first highly efficient double Friedel-Crafts reaction of N-tosyl imines with anisole, phenol, thioanisole and analogues has been developed to produce the corresponding symmetric diarylmethanes and triarylmethanes with high regioselectivity in the presence of a catalytic amount of Bi2(SO 4)3-TMSCl at room temperature. The Royal Society of Chemistry.
- Liu, Cong-Rong,Li, Man-Bo,Yang, Cui-Feng,Tian, Shi-Kai
-
p. 1249 - 1251
(2008/12/21)
-