- An extremely fast and efficient acylation reaction of alcohols with acid anhydrides in the presence of trimethylsilyl trifluoromethanesulfonate as catalyst
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Alcohols are converted to esters in a fast, clean and efficient reaction with acid anhydrides in the presence of trimethylsilyl trifluoromethanesulfonate.
- Procopiou, Panayiotis A.,Baugh, Simon P. D.,Flack, Stephen S.,Inglis, Graham G. A.
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- Synthesis of 1,2-Dihydro-Substituted Aniline Analogues Involving N -Phenyl-3-aza-Cope Rearrangement Using a Metal-Free Catalytic Approach
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An efficient metal-free domino reaction leading to structural/electronically divergent 1,2-dihydropyridines from easily accessible propargyl vinyl anilines via N-phenyl 3-aza-Cope sigmatropic rearrangement is reported with good to excellent yields using 1,2-dichlorobenzene as solvent under thermal conditions. Spirocyclic substitution is also tolerated under the present optimized conditions.
- Alduhaish, Osamah,Varala, Ravi,Adil, Syed Farooq,Khan, Mujeeb,Siddiqui, Mohammed Rafiq H.,Alwarthan, Abdulrhman,Alam, M. Mujahid
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- Palladium-Catalyzed [2+1] Cycloadditions Affording Vinylidenecyclopropanes as Precursors of 7-Membered Carbocycles
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Palladium(II) acetate in association with secondary phosphine oxides provides an efficient catalytic system for [2+1] cycloadditions starting from oxanorbornene derivatives and tertiary propargyl esters giving rise to vinylidenecyclopropanes. This reaction is specific to bidentate phosphinito-phosphinous acid ligands generated from secondary phosphine oxides. The [2+1] cycloaddition was found broad in scope with a high tolerance to various functional groups. Moreover, vinylidenecyclopropanes were straightforwardly converted into oxabicyclo[3.2.1]oct-2-ene derivatives through a palladium-catalyzed ring-expansion. Finally, the oxa bridge cleavage of oxatricyclic compounds yields functionalized 7-membered carbocycles.
- Lepronier, Aymeric,Achard, Thierry,Giordano, Laurent,Tenaglia, Alphonse,Buono, Gerard,Clavier, Herve
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supporting information
p. 631 - 642
(2016/02/27)
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- An unprecedented Pd-catalyzed, water-promoted sequential oxidative aminocarbonylation-cyclocarbonylation process leading to 2-oxazolidinones
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An unprecedented, Pdl2-catalyzed, sequential oxidative aminocarbonylation-cyclocarbonylation process, leading to 2-oxazolidinone derivatives 3 in good to excellent yields starting from readily available α,α-disubstituted 2-ynylamines 1 and secondary amines 2, is reported. In the case of an α-monosubstituted substrate, the initially formed 2-oxazolidinone derivative underwent shift of the double bond to give a 3H-oxazol-2-one derivative in excellent isolated yield.
- Gabriele, Bartolo,Plastina, Pierluigi,Salerno, Giuseppe,Mancuso, Raffaella,Costa, Mirco
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p. 3319 - 3322
(2008/02/12)
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- Synthesis of N-propargylanabasine derivatives by the mannich reaction
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N-Propargylanabasine derivatives bearing various substituents at the carbon atom of the alkyne fragment were obtained by the reaction of anabasine hydrochloride with terminal alkynes and paraformaldehyde. The reaction proceeded with retention of the C(2) chiral center in anabasine fragment. The by-products of the reaction, including 1,3-diacetylene (the products of dimerization of alkynes) and conjugated vinylacetylenes (the rearrangement products of the Mannich adducts) were isolated and characterized.
- Mavrov,Zlotin
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p. 1637 - 1647
(2008/09/18)
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- Zirconiuni(IV) chloride as a new, highly efficient, and reusable catalyst for acetylation of phenols, thiols, amines, and alcohols under solvent-free conditions
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Zirconium(IV) chloride has been found to be a new, highly efficient, and reusable catalyst for acetylation of structurally diverse phenols, thiols, amines, and alcohols under solvent-free condtions. Acetylation of sterically hindered and electron deficient phenols is achieved in excellent yields with stoichiometric amounts of Ac2O at room temperature. Acid-sensitive alcohols undergo acetylation with excellent chemoselectivity without competitive side reactions such as dehydration or rearrangement. The mild Lewis acid property of the catalyst enables the acetylation to be carried out with optically active substrates without any detrimental effect on the optical purity.
- Chakraborti, Asit K.,Gulhane, Rajesh
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p. 627 - 630
(2007/10/03)
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- Fluoroboric acid adsorbed on silica gel as a new and efficient catalyst for acylation of phenols, thiols, alcohols, and amines
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Fluoroboric acid supported on silica gel efficiently catalyzes acylation of structurally diverse phenols, alcohols, thiols, and amines under solvent free conditions. Acid-sensitive alcohols are smoothly acylated without competitive side reactions.
- Chakraborti, Asit K.,Gulhane, Rajesh
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p. 3521 - 3525
(2007/10/03)
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- Indium(III) chloride as a new, highly efficient, and versatile catalyst for acylation of phenols, thiols, alcohols, and amines
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Indium(III) chloride efficiently catalyses the acylation of structurally diverse phenols, alcohols, thiols, and amines under solvent free conditions. Acid sensitive alcohols are smoothly acylated without competitive side reactions. Acylation of 2-hydroxynaphthalene is carried out with carboxylic acids adopting the mixed anhydride protocol using trifluoroacetic anhydride.
- Chakraborti, Asit K.,Gulhane, Rajesh
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p. 6749 - 6753
(2007/10/03)
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- Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines
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Perchloric acid adsorbed on silica gel efficiently catalyses acetylation of structurally diverse phenols, alcohols, thiols, and amines under solvent free conditions.
- Chakraborti, Asit K.,Gulhane, Rajesh
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p. 1896 - 1897
(2007/10/03)
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- Electrostatic catalysis by ionic aggregates: Scope and limitations of Mg(ClO4)2 as acylation catalyst
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Alkali and alkaline earth metal perchlorates exhibit electrostatic catalysis in the activation of anhydrides for the acylation reaction. Perchlorates with higher values of the charge-size function of the metal ion exhibit better catalytic activity following the order Mg(ClO4) 2>Ba(ClO4)2>LiClO4. Acylation of structurally diverse phenols, thiols, alcohols, and amines have been carried out with stoichiometric amounts of anhydride at room temperature under solvent free conditions in the presence of catalytic amount of Mg(ClO4) 2. Sterically hindered and electron deficient phenols are efficiently acylated. Acylation with sterically hindered anhydrides such as iso-butyric, pivalic, and benzoic anhydrides are carried out with phenols and alcohols in excellent yields. Acid-sensitive alcohols are acylated in excellent yields without any competitive side reactions.
- Chakraborti, Asit K.,Sharma, Lalima,Gulhane, Rajesh,Shivani
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p. 7661 - 7668
(2007/10/03)
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- An Extremely Powerful Acylation Reaction of Alcohols with Acid Anhydrides Catalyzed by Trimethylsilyl Trifluoromethanesulfonate
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Trimethylsilyl trifluoromethanesulfonate is an excellent catalyst for the acylation of alcohols with acid anhydrides. Highly functionalized primary, secondary, tertiary, and allylic alcohols, and phenols, were acylated cleanly and efficiently and in a fraction of the time used under the standard DMAP conditions.
- Procopiou, Panayiotis A.,Baugh, Simon P.D.,Flack, Stephen S.,Inglis, Graham G.A.
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p. 2342 - 2347
(2007/10/03)
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- A NEW METHOD FOR THE SYNTHESIS OF VINYL- AND DI-ALLENES ASSISTED BY ORGANOALUMINIUM CONPOUNDS
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The interactions of organoaluminium reagents with acetates of substituted propargyl alcohols have been considered as the most appropriate method to synthesize allenes.Studies have been carried out on the synthesis of vinyl- and di-allenes, employing both
- Tolstikov, G. A.,Romanova, T. Yu.,Kuchin, A. V.
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