- Solid-Phase Benzoylation of Phenols and Alcohols in Microwave Reactor: An Ecofriendly Protocol
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An efficient solid-phase benzoylation of phenols and alcohols was developed under microwave irradiation. A stoichiometric amount of benzoyl chloride was sufficient to carry out the reaction. This benzoylation features short reaction time, good yields, and easy workup procedures. Furthermore, the scope of the reaction was extended to prepare 3,5-dinitrobenzoyl derivatives of alcohols.
- Chakraborty, Suchandra,Saha, Ahana,Basu, Kaushik,Saha, Chandan
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supporting information
p. 2331 - 2343
(2015/10/12)
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- HF-Pyridine: A versatile promoter for monoacylation/sulfonylation of phenolic diols and for direct conversion of t-butyldimethylsilyl ethers to the corresponding acetates
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Monoacylation and trifluoromethanesulfonylation of phenolic diols were achieved by the aid of HF-pyridine, whereas diacylation occurred with pyridine alone. Furthermore, HF-pyridine was found to promote the direct conversion of t-butyldimethylsilyl ethers to the corresponding acetates.
- Michigami, Kyosuke,Yoshimoto, Kazuya,Hayashi, Masahiko
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scheme or table
p. 138 - 139
(2012/03/09)
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- 3,6-Dibenzoxyl-1,2-pyridazine: A new versatile benzoyl transferring agent for NH2, -OH and -SH benzoylations
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A newly synthesized 3,6-dibenzoxyl-1,2-pyridazine 3 has been investigated for its potential to transfer the benzoyl group to various organic substrates carrying -NH2, -OH and -SH groups. The benzoyl transfer is fairly general in scope, occurs under convenient conditions and provides good to excellent yields of benzoylated products. Moreover, by choosing proper conditions, it is possible to achieve chemoselective benzoylation in bi-functional molecules. For instance, N-benzoylation of aromatic amines can be selectively accomplished over that of aliphatic amines and vice versa by manipulating reaction conditions. Selective N- or O-benzoylation in aminophenols is also possible. Although, not studied in detail, we final that dibenzoate 3 can also be used to effect C-benzoylation of reactive phenols and ketones, as exemplified by the C-benzoylation of resorcinol and acetophenone, respectively. Dibenzoate 3, besides being a crystalline, easy to handle, solid possesses twice the potential as an acyl carrier compared to the other known acyl carriers. These features make 3 as an attractive choice for many applications pertaining to benzoyl transfer reactions.
- Mashraqui, Sabir Hussain,Shivaji, Jadhav Latika
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p. 927 - 935
(2007/10/03)
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- PhCOCI-Py/basic alumina as a versatile reagent for benzoylation in solvent-free conditions
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A solvent-free procedure using PhCOCl-Py/basic alumina under microwave irradiation has been developed for N-, O- and S-benzoylation.
- Paul, Satya,Nanda, Puja,Gupta, Rajive
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p. 374 - 380
(2007/10/03)
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- Kinetically controlled diastereoselective synthesis of CPS124, a carnitine monothiophosphate
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An expedient synthesis of CPS124 (1) is described using the diastereoselective reaction of the in situ generated dichlorophosphite 6 with L-carnitine tetrafluoroborate salt 7 under kinetic control as the key step. Alkylations of resorcinol 2 and its benzoate 13 are discussed. The use of α-cellulose as a support for solids that are difficult to filter or low melting is presented.
- Prasad, Kapa,Xu, David D.,Tempkin, Orin,Villhauer, Edwin B.,Repic, Oljan
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p. 743 - 749
(2013/09/05)
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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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- Bismuth(III) salts as convenient and efficient catalysts for the selective acetylation and benzoylation of alcohols and phenols
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Efficient acetylation and benzoylation of alcohols and phenols with acetic and benzoic anhydrides have been carried out under catalysis of bismuth(III) salts including BiCl3, Bi(TFA)3 and Bi(OTf)3. Selective acetylation and benzoylation of alcohols in the presence of phenols is an additional advantage of this procedure.
- Mohammadpoor-Baltork, Iraj,Aliyan, Hamid,Reza Khosropour, Ahmad
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p. 5851 - 5854
(2007/10/03)
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- Scandium trifluoromethanesulfonate as an extremely active Lewis acid catalyst in acylation of alcohols with acid anhydrides and mixed anhydrides
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Scandium trifluoromethanesulfonate (triflate), which is commercially available, is a practical and useful Lewis acid catalyst for acylation of alcohols with acid anhydrides or the esterification of alcohols by carboxylic acids in the presence of p-nitrobenzoic anhydrides. The remarkably high catalytic activity of scandium triflate can be used for assisting the acylation by acid anhydrides of not only primary alcohols but also sterically-hindered secondary or tertiary alcohols. The method presented is especially effective for selective macrolactonization of ω-hydroxy carboxylic acids.
- Ishihara, Kazuaki,Kubota, Manabu,Kurihara, Hideki,Yamamoto, Hisashi
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p. 4560 - 4567
(2007/10/03)
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