Acetonyltriphenylphosphonium Bromide (ATPB): A Versatile Reagent for the Acylation of Alcohols, Phenols, Thiols and Amines and for 1,1‐Diacylation of Aldehydes under Solvent‐Free Conditions

Khan, Abu T.; Choudhury, Lokman H.; Ghosh, Subrata

doi:10.1002/ejoc.200500066

Cited by 38 publications

(14 citation statements)

References 46 publications

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“…Some notable methods include the use of I 2 [2][3][4], Br 2 [5] montmorillonite K-10 [6], FeCl 3 [7], TiCl 4 -AgClO 4 [8], LiClO 4 [9], CuSO 4 ·5H 2 O [10], TMSOTf [11], Bu 3 P in CH 2 Cl 2 [12,13], La(NO 3 ) 3 ·6H 2 O [14], HClO 4 -SiO 2 [15], molecular sieves [16], NaHCO 3 [17], Mg(NTf 2 ) 2 [18], 3-nitrobenzeneboronic acid [19], alumina [20], NBS [21], TaCl 5 [22], VO(OAc) 2 [23] and metal triflates such as Pd(PhCN) 2 (OTf) [24], Cu(OTf) 2 [25], Bi(OTf) 2 [26], In(OTf) 2 [27,28], Sc(OTf) 2 [29], Ce(OTf) 2 [30], and CoCl 2 [31,32].…”

Section: Introductionmentioning

confidence: 99%

Mild and Highly Efficient Copper(I) Inspired Acylation of Alcohols and Polyols

Mensah

Earl

2017

Catalysts

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A new and highly efficient method mediated by tetrakis(acetonitrile)copper(I) triflate for activating both simple and highly hindered anhydrides in the acylation of alcohols and polyols is described. This new acylation method is mild and mostly proceeds at room temperature with low catalyst loading. The method is versatile and has been extended to a wide variety of different alcohol substrates to afford the corresponding ester products in good to excellent yields.

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Section: Introductionmentioning

confidence: 99%

Mild and Highly Efficient Copper(I) Inspired Acylation of Alcohols and Polyols

Mensah

Earl

2017

Catalysts

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“…Under solvent-free conditions, a general and practical method has been extended to synthesize esters, thioesters and amides derivatives. 48 Acetonyltriphenylphosphonium bromide (ATPB; 5 mol%) at room temperature was designed as an efficient and versatile system for the acylation of alcohols, phenols, thiols and amines (Scheme 2). Scheme 2.…”

Section: Solvent-free Acylation Reactionsmentioning

confidence: 99%

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Kazemi

Sanchez-Mendoza

Ghobadi

2019

JMCS

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The hazardous and toxic nature of many solvents, in particular organic solvents that are extensively used in large scale for organic reactions have transformed a serious threat to the environment. Therefore, the design of solvent-free catalytic reaction has received considerable attention during recent times in the field of green synthesis. A solvent-free or solid state reaction may be accomplished using the reactants single or merge them in clays, zeolites, silica, alumina or other substrates. Esters, thioesters and amides are important and valuable compounds in the area of industry, medicine, pharmaceutical and heterocyclic chemistry. In this paper, various solventfree systems to synthesize esters, thioesters and amides via the acylation of alcohols, phenols, thiols and amines are described. In this review we summarized the activities presented mainly the recent years. reusable catalyst for the synthesis of esters and amides under solvent-free conditions (Scheme 5). 50 Scheme 3. Solvent-free diacylation of aldehydes using ATPB. Scheme 4. Solvent-free acylation of alcohols, thiols and amines catalyzed by ZrOCl 2 .8H 2 O.An convenient method with the same reagents and in the presence of lithium bis(perfluoroalkylsulfonyl)-imide (LiPFS-I) has also been developed (Scheme 24). 76 Scheme 24. Solvent-free acylation of alcohols using LiPFSI.Another practical and highly efficient strategy was also described with SiO 2 -Co(acac) 2 and SiO 2 -Cu(acac) 2 under solvent-free conditions (Scheme 25). 77 The acylation of alcohols, phenols and amines with acetyl chloride was carried out in less than 60 min at 50 0 C. The esterification of alcohols and amines was performed respectively with SiO 2 -Cu(acac) 2 and SiO 2 -Co(acac) 2. Scheme 25. Solvent-free acylation of alcohols and amines using SiO 2 -Co(acac) 2 and SiO 2 -Cu(acac) 2 . 7 M. Kazemi et al Journal of Medicinal and Chemical Sciences Review J. Med. Chem. Sci. 2019, 1, 1-8 http://jmchemsci.com Scheme 30. Solvent-free diacylation of aldehydes catalyzed by n-Sulfonic acid poly4-vinylpyridinum) hydrogen sulfate.

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“…Cu(OTf) 2 [19], Sc(OTf) 3 [20] and Bi(OTf) 3 [21] have also been utilized as catalysts for the preparation of 1,1-diacetate derivatives from the corresponding aldehydes. Very recently, we have demonstrated the applicability of acetonyltriphenylphosphonium bromide (ATPB) [22] and bromodimethylsulfonium bromide (BDMS) [23] for acetylation of alcohols, phenols, amines and thiols and for 1,1-diacylation of aldehydes. Unfortunately, many of these methods have drawbacks such as harsh reaction conditions, requirement of excess amount of acetic anhydride, tedious workup procedure and involvement of expensive and moisture sensitive catalyst.…”

Section: Introductionmentioning

confidence: 99%