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Bi(OTf)3-catalysed domino Friedel-Crafts alkylation of arenes with aldehydes: An upgraded method for efficient synthesis of triarylmethanes and anthracene derivatives
, Article Tetrahedron ; Volume 72, Issue 11 , March , 2016 , Pages 1433–1439 ; 00404020 (ISSN) ; Mohammadpoor Baltork, I ; Tangestaninejad, S ; Moghadam, M ; Mirkhani, V ; Kia, R ; Sharif University of Technology
Elsevier Ltd
2016
Abstract
A variety of novel triarylmethanes including bis-(dihexyloxyphenyl)arylmethanes and diveratrylmethanes were prepared by the domino Friedel-Crafts alkylation of arenes with aldehydes catalysed by Bi(OTf)3. The reaction of veratrole with aromatic dialdehydes afforded different results based on the molar ratio of reactants and the nature of aromatic dialdehydes. Bi(OTf)3/O2 is shown to be a highly efficient reagent system to promote the tandem three-step reaction of acylals with bis-(dihexyloxyphenyl)arylmethanes or diveratrylmethanes for the preparation of 9,10-disubstituted-2,3,6,7-tetraalkoxyanthracenes. The substrate scope, the simplicity of the reactions and work-up processes, besides a...
Bi(OTf)3-catalysed domino Friedel-Crafts alkylation of arenes with aldehydes: An upgraded method for efficient synthesis of triarylmethanes and anthracene derivatives
, Article Tetrahedron ; Volume 72, Issue 11 , 2016 , Pages 1433-1439 ; 00404020 (ISSN) ; Mohammadpoor Baltork, I ; Tangestaninejad, S ; Moghadam, M ; Mirkhani, V ; Kia, R ; Sharif University of Technology
Elsevier Ltd
Abstract
A variety of novel triarylmethanes including bis-(dihexyloxyphenyl)arylmethanes and diveratrylmethanes were prepared by the domino Friedel-Crafts alkylation of arenes with aldehydes catalysed by Bi(OTf)3. The reaction of veratrole with aromatic dialdehydes afforded different results based on the molar ratio of reactants and the nature of aromatic dialdehydes. Bi(OTf)3/O2 is shown to be a highly efficient reagent system to promote the tandem three-step reaction of acylals with bis-(dihexyloxyphenyl)arylmethanes or diveratrylmethanes for the preparation of 9,10-disubstituted-2,3,6,7-tetraalkoxyanthracenes. The substrate scope, the simplicity of the reactions and work-up processes, besides a...
Efficient Friedel-crafts alkylation of indoles and pyrrole with enones and nitroalkene in water
, Article Organic and Biomolecular Chemistry ; 2006, Volume 4, Issue 23, Pages 4275-4277 ; Arynasab, F ; Saidi, M. R ; Sharif University of Technology
Abstract
An operationally simple and entirely green protocol for heteropoly acid catalyst conjugate addition of indoles and pyrrole to unsaturated carbonyl compounds and nitro-alkene in water was investigated. It is important that the products arising from 1,2-addition were not observed under the reaction conditions. Pyrroles also readily underwent Michael addition at Α-positions under the same reaction conditions. Indole and many of its derivatives are present in many substances commonly found in nature. Micheal addition reactions are performed in organic solvents with the reactions in water are relatively scarce. The Michael addition between indole and methyl vinyl ketone in the presence of...
Efficient Friedel-crafts alkylation of indoles and pyrrole with enones and nitroalkene in water
, Article Organic and Biomolecular Chemistry ; Volume 4, Issue 23 , 2006 , Pages 4275-4277 ; 14770520 (ISSN) ; Arynasab, F ; Saidi, M. R ; Sharif University of Technology
2006
Abstract
An operationally simple and entirely green protocol for heteropoly acid catalyst conjugate addition of indoles and pyrrole to unsaturated carbonyl compounds and nitro-alkene in water was investigated. It is important that the products arising from 1,2-addition were not observed under the reaction conditions. Pyrroles also readily underwent Michael addition at Α-positions under the same reaction conditions. Indole and many of its derivatives are present in many substances commonly found in nature. Micheal addition reactions are performed in organic solvents with the reactions in water are relatively scarce. The Michael addition between indole and methyl vinyl ketone in the presence of...