- Application of poly(Vinylbenzyltrimethylammonium tribromide) resin as an efficient polymeric catalyst in the acetalization and diacetylation of benzaldehydes
-
The applications of a new supported tribromide reagent (poly(vinylbenzyltrimethylammonium tribromide) resin) were reported. This supported tribromide resin was used as a catalyst in the acetalization and diacetylation of benzaldehydes under mild conditions with high efficiency. The effects of solvents, and amount of the supported tribromide resin on the reactions were investigated. Under the optimal conditions, most of acetal and 1,1-diacetates of benzaldehydes were selectively obtained in excellent yields.
- Han, Bingbing,Hu, Junjun,Li, Xianwei,Zheng, Zubiao
-
supporting information
p. 287 - 293
(2021/04/28)
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- Transition-Metal-Free Synthesis of Polyfunctional Triarylmethanes and 1,1-Diarylalkanes by Sequential Cross-Coupling of Benzal Diacetates with Organozinc Reagents
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A variety of functionalized triarylmethane and 1,1-diarylalkane derivatives were prepared via a transition-metal-free, one-pot and two-step procedure, involving the reaction of various benzal diacetates with organozinc reagents. A sequential cross-coupling is enabled by changing the solvent from THF to toluene, and a two-step SN1-type mechanism was proposed and evidenced by experimental studies. The synthetic utility of the method is further demonstrated by the synthesis of several biologically relevant molecules, such as an anti-tuberculosis agent, an anti-breast cancer agent, a precursor of a sphingosine-1-phosphate (S1P) receptor modulator, and a FLAP inhibitor.
- Wei, Baosheng,Ren, Qianyi,Bein, Thomas,Knochel, Paul
-
supporting information
p. 10409 - 10414
(2021/03/26)
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- The studies on chemoselective promiscuous activity of hydrolases on acylals transformations
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Chemoselective, mild and convenient protocol for the hydrolysis of the synthetically relevant acylals via promiscuous enzyme-catalyzed hydrolysis has been developed. It has been shown that promiscuous activity of the used hydrolases dominates their native activity related with carboxylic esters hydrolysis. The main advantage of the present methodology is that it can be conducted under neutral conditions at room temperature. Moreover, complete deprotection of acylals takes place within 10–20 min. Developed protocol can be used with compounds having a variety of hydrolytic labile groups since the cleavage is proceeded under neutral conditions and occurs exclusively on acylal moiety. Further this protocol was extended by the tandem Passerini multicomponent reaction leading to the α-acetoxy amides using acylals as the surrogates of the carbonyl components to P-MCR.
- Koszelewski, Dominik,Ostaszewski, Ryszard
-
-
- Chemoselective synthesis of 1,1-diacetates under solvent-free condition using efficient heterogeneous ecofriendly catalyst: P2O5/kaolin
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An efficient and chemoselective method for the preparation of acylals from different aldehydes and acetic anhydride using.....kaolin supported catalyst (P2O5). under solvent-free conditions is described herein. The present protocol offers several advantages including use of inexpensive and non-toxic catalyst support i.e., natural kaolin. Preparation of the supported catalyst is easy, the process is simple in operation, maintaining solvent free conditions, with short reaction times, high yields and affording selective protection of aldehyde in presence of ketone.
- Rai, Nityanand,Sharma, Abha
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p. 340 - 344
(2019/05/21)
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- Supported N-propylsulfamic acid onto Fe3O4 magnetic nanoparticles as a reusable and efficient nanocatalyst for the protection/deprotection of hydroxyl groups and protection of aldehydes
-
N-propylsulfamic acid supported onto Fe3O4 magnetic nanoparticles (MNPs-PSA) as an efficient and magnetically reusable nanocatalyst has been reported for the tetrahydropyranylation/depyranylation of a wide variety of alcohols and phenols by changing the solvent medium. Also, the protection of aldehydes as acylals using Ac2O in the presence of catalytic amount MNPs-PSA in good to high yields at room temperature under solvent-free conditions is described. After completing the reaction, the catalyst was easily separated from the reaction mixture with the assistance of an external magnetic field and reused for several consecutive runs without significant loss of their catalytic efficiency.
- Rostami, Amin,Tahmasbi, Bahman,Abedi, Fatemeh
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p. 3689 - 3701
(2016/04/05)
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- Zinc zirconium phosphate as an efficient catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions
-
In the present study, a mild, rapid, and efficient method for the protection of aldehydes with acetic anhydride (AA) in the presence of zinc zirconium phosphate (ZPZn) as a nano catalyst, at room temperature is reported. Selective conversion of aldehydes was observed in the presence of ketones. Under these conditions, different aldehydes bearing electron-withdrawing and electron-donating substituents were reacted with AA and the corresponding 1,1-diacetates (acylals) were obtained in high to excellent yields. The steric and electronic properties of the different substrates had a significant influence on the reaction conditions. Also, the deprotection of 1,1-diacetates has been achieved using this catalyst in water. This nanocatalyst was characterized by several physico-chemical techniques. It was recovered easily from the reaction mixture, regenerated and reused at least 7 times without significant loss in catalytic activity. This protocol has the advantages of easy availability, stability, reusability of the eco-friendliness, chemoselectivity, simple experimental and work-up procedure, solvent-free conditions and usage of only a stoichiometric amount of AA.
- Hajipour, Abdol R,Karimi, Hirbod
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p. 1945 - 1955
(2015/12/30)
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- Green procedures for the chemoselective synthesis of acylals and their cleavage promoted by recoverable sulfonic acid based nanoporous carbon (CMK-5-SO3H)
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A selective synthesis of gem-diacetates from the reaction of aldehydes and acetic anhydride in the presence of recyclable nanoporous solid sulfonic acid (CMK-5-SO3H) under solvent-free reaction conditions is reported. The catalyst was also found to be highly active for deprotection of resulting acylals in water. [Figure not available: see fulltext.]
- Zareyee, Daryoush,Mirzajanzadeh, Ehsan,Khalilzadeh, Mohammad Ali
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p. 1229 - 1234
(2015/10/06)
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- Sulfonated rice husk ash (RHA-SO3H): A highly powerful and efficient solid acid catalyst for the chemoselective preparation and deprotection of 1,1-diacetates
-
Rice husk ash (RHA), as a source of amorphous silica, was treated with chlorosulfonic acid and sulfonated rice husk ash (RHA-SO3H) as a highly powerful solid acid catalyst was obtained and characterized with a variety of techniques including IR, TGA, SEM, XRD, pH analysis, Hammett acidity function and BET method. This solid acid showed excellent catalytic activity for the protection and deprotection of aldehydes with Ac2O at room temperature under solvent free conditions. The procedure gave the products in excellent yields in very short reaction times and good to high yields. Also this catalyst can be reused for several times without loss of its catalytic activity.
- Shirini, Farhad,Mamaghani, Manouchehr,Seddighi, Mohadeseh
-
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- Chemoselective synthesis of geminal diacetates (acylals) using eco-friendly reusable propylsulfonic acid based nanosilica (SBA-15-Ph-PrSO3H) under solvent-free conditions
-
An expeditious method for the acetylation of aldehydes by mesoporous solid sulfonic acid (SBA-15-Ph-PrSO3H) under solvent-free reaction conditions was described. The route furnished selectively and in excellent yields the corresponding 1,1-diacetates starting from aldehydes and acetic anhydride using the environmentally friendly catalyst. The catalyst was found to be highly active and selective and could be recycled several times.
- Zareyee, Daryoush,Moosavi, Sayed M.,Alaminezhad, Alireza
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p. 227 - 231
(2013/08/23)
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- Solvent-free catalytic preparation of 1,1-diacetates using a silica-supported functional ionic liquid as catalyst
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An efficient and convenient preparation of acylals from aldehydes and acetic anhydride, under solvent-free conditions, in the presence of a silica-supported functional ionic liquid, Si-[SbSipim][PF6], is reported. Si-[SbSipim][PF6] acts as a catalyst and can be recovered and reused four times without apparent loss of its catalytic activity.
- Kang, Li Q.,Cai, Yue Q.,Cheng, Lin
-
p. 247 - 249
(2013/07/27)
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- Rice husk supported FeCl3 nanoparticles as an efficient and reusable catalyst for the chemoselective 1,1-diacetate protection and deprotection of aldehydes
-
1,1-Diacetates were produced from a variety of aromatic aldehydes using rice husk supported FeCl3 nanoparticles as a catalyst. The procedure generally resulted in good yields (98%) of aromatic aldehydes including those carrying electron donating- or withdrawing-substituents. Deprotection of the resulting 1,1-diacetates was also achieved using the same catalyst in ethanol. This new method consistently has the advantages of excellent yields and relatively short reaction times. Further, the catalyst can be reused and recovered for several times.
- Shirini, Farhad,Akbari-Dadamahaleh, Somayeh,Mohammad-Khah, Ali
-
-
- An efficient method for the transthioacetalization of acylals and acetals under mild conditions
-
A rapid and efficient method for the transthioacetalization of acylals (1,1-diacetates) and acyclic and cyclic acetals is described. The reaction was carried out using 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane tribromide (1 mol%). The yield of the transthioacetalization was high and reaction conditions involve the use of acetonitrile as the solvent at room temperature; isolation is simple and the products are nearly pure.
- Pourmousavi, Seied Ali,Hadavankhani, Majid,Zinati, Zahra
-
experimental part
p. S495-S501
(2012/05/31)
-
- [HSO3-pmim][CH3SO3] as an efficient catalyst for chemoselective synthesis of 1,1-diacetates under ultrasound irradiation
-
A mild and efficient method for the chemoselective preparation of 1,1-diacetates catalyzed by 1-methyl-3-(3- sulfopropyl)-imidazolium methyl sulfate under ultrasound irradiation has been developed. The yields are ranged in 90%-98%. This protocol offered several advantages including low catalyst loading, high yields, short reaction time and environmentally benign approach.
- Li, Chao,Guo, Tao,Zhou, Xin,Wang, Chun,Ma, Jing-Jun,Li, Jin-Bin
-
experimental part
p. 484 - 487
(2012/04/11)
-
- A simple and fast method for protection of aldehydes as 1,1-diacetates using cerium(IV) sulfate as an efficient and reusable inorganic catalyst
-
A simple, green, and very fast method for protection of aryl aldehydes as 1,1-diacetates promoted by cerium(IV) sulfate tetrahydrate, Ce(SO 4)2·4H2O, as a novel inorganic solid acid catalyst at room temperature and under solvent-free conditions is described. The present methodology offers several advantages, such as a simple procedure with an easy workup, very short reaction times, high yields, and the absence of any volatile and hazardous organic solvents. Copyright Taylor & Francis Group, LLC.
- Saburi, Elahe,Davoodnia, Abolghasem,Tavakoli-Hoseini, Niloofar
-
experimental part
p. 1063 - 1066
(2012/02/16)
-
- A convenient and efficient protocol for the synthesis of acylals catalyzed by Br?nsted acidic ionic liquids under ultrasonic irradiation
-
The synthesis of acylals (1,1-diacetates) via the reactions of aldehydes with acetic anhydride was carried out in 85-97% yields at room temperature under ultrasound irradiation catalyzed by the Br?nsted acidic ionic liquid [bmpy]HSO4. This method provides several advantages, such as solvent-free conditions, operational simplicity, higher yields, and reduced environmental consequences. The ionic liquid was recovered and reused.
- Borikar, Sanjay P.,Daniel, Thomas
-
experimental part
p. 928 - 931
(2012/03/08)
-
- H3PW12O40-catalysed alkylation of arenes and diveratrylmethanes: Convenient routes to triarylmethanes and to symmetrical and unsymmetrical 9,10-diaryl-2,3,6,7-tetramethoxyanthracenes
-
An efficient method for the synthesis of triarylmethanes and difurylarylmethanes through solventless reactions between aldehydes and arenes in the presence of H3PW12O40 as a reusable catalyst under thermal and microwave irradiation conditions has been developed. H3PW12O40-catalysed one-pot consecutive Friedel-Crafts reactions between veratrole and aldehydes were also applied as a convenient protocol for the preparation of symmetrical 9,10-diaryl-2,3,6,7- tetramethoxyanthracenes.
- Mohammadpoor-Baltork, Iraj,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammadiannejad-Abbasabadi, Kazem,Khavasi, Hamid R.
-
scheme or table
p. 1357 - 1366
(2011/04/17)
-
- Mild and chemoselective synthesis and deprotection of geminal diacetates catalyzed by titanium(IV) halides
-
A novel, mild, and chemoselective method was developed for the preparation of gem-diacetates from aldehydes and acetic anhydride in the presence of titanium(IV) fluoride (1-5 mol%) under solvent-free conditions at room temperature. The reaction showed a high chemoselectivity toward aldehydes in the presence of ketones. Moreover, titanium(IV) fluoride also catalyzed the deprotection of gem-diacetates to the corresponding aldehydes in water. This efficient and simple method has several benefits, including the use of an inexpensive catalyst, solvent-free conditions, mild reaction temperatures, and high yields, which make it both cost-effective and environmentally friendly. Georg Thieme Verlag Stuttgart.
- Jung, Misuk,Yoon, Jieun,Kim, Hak Sung,Ryu, Jae-Sang
-
experimental part
p. 2713 - 2720
(2010/10/02)
-
- NbCl5 as an efficient catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions
-
A mild and efficient method for the chemoselective preparation of 1,1-diacetates catalyzed by NbCl5(5mmol%) under solvent-free conditions has been developed. The yields are in the range of 93-98%. This protocol offered several advantages, including low catalyst loading, good yields, short reaction times, and environmentally friendliness.
- Gao, Shu-Tao,Zhao, Ying,Li, Chao,Ma, Jing-Jun,Wang, Chun
-
experimental part
p. 2221 - 2229
(2009/10/17)
-
- Silica-bonded S-sulfonic acid as a recyclable catalyst for chemoselective synthesis of 1,1-diacetates
-
A simple and efficient procedure for the preparation of silica-bonded S-sulfonic acid (SBSSA) by reaction of 3-mercaptopropylsilica (MPS) and chlorosulfonic acid in chloroform is described. This solid acid is employed as a recyclable catalyst for the synthesis of 1,1-diacetates from aromatic aldehydes and acetic anhydride under mild and solvent-free conditions at room temperature.
- Niknam, Khodabakhsh,Saberi, Dariush,Sefat, Maryam Nouri
-
scheme or table
p. 4058 - 4062
(2009/10/11)
-
- An efficient method for the synthesis of acylals from aldehydes under solvent-free conditions catalyzed by antimony trichloride
-
A mild and efficient method has been developed for the preparation of acylals from aldehydes catalyzed by antimony trichloride under solvent-free conditions in very good to excellent yields. The easy availability, low cost, and ease of handling of the catalyst make this procedure especially attractive for large-scale synthesis. Copyright Taylor & Francis Group, LLC.
- Bhattacharya, Asish K.,Mujahid, Mohammad,Natu, Arvind A.
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p. 128 - 134
(2008/03/14)
-
- Thallium(III) chloride: A mild and efficient catalyst for acylation of alcohols, phenols and thiols, and for geminal diacylation of aldehydes under solvent-free conditions
-
Thallium(III) chloride is a simple and efficient catalyst for acylation of alcohols, phenols and thiols. It is also very effective for geminal diacylation of aldehydes. The acylation reaction using acetic anhydride proceeds in excellent yield in the presence of catalytic amounts of thallium(III) chloride (1 mol%) at room temperature within relatively short reaction times (20 min). Structurally diverse alcohols, phenols, thiols and aldehydes undergo acylation under solvent-free conditions.
- Kadam, Santosh T.,Kim, Sung Soo
-
experimental part
p. 3307 - 3313
(2009/05/07)
-
- Solid superacids as catalysts for the synthesis of acylals from aldehydes and acetic anhydride
-
Sulfated tin, aluminum, and titanium oxides are efficient catalysts for reactions of aldehydes with acetic anhydride leading to acylals.
- Lermontov,Yurkova
-
experimental part
p. 2561 - 2563
(2010/04/29)
-
- A facile and efficient conversion of aldehydes into 1,1-diacetates (acylals) using iron(III) fluoride as a novel catalyst
-
Aldehydes are smoothly converted into the corresponding 1,1-diacetates (acylals) in high yields in the presence of a catalytic amount (0.1 mol-%) of iron(III) fluoride at room temperature. The noteworthy features of the present system are shorter reaction times, chemoselective protection of aldehydes, and solvent-free conditions. The procedure is especially useful for large-scale syntheses as the catalyst is highly effective from the view of activity, selectivity, reusability, and economy in the preparation of 1,1-diacetates (acylals). CSIRO 2007.
- Kamble,Tayade,Davane,Kadam
-
p. 590 - 594
(2008/03/11)
-
- A versatile and practical synthesis of 1,1-diacetates from aldehydes catalyzed by cyanuric chloride
-
Structurally diverse aldehydes are successfully converted into 1,1-diacetates with acetic anhydride using cyanuric chloride as a mild, convenient and inexpensive catalyst under solvent-free conditions. The noteworthy features of the present system are shorter reaction times, and mild and solvent-free conditions. Furthermore, it offers chemoselective protection of aldehydes.
- Bandgar, Babasaheb P.,Joshi, Neeta S.,Kamble, Vinod T.
-
p. 489 - 492
(2008/02/11)
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- Preparation of geminal diacylates (acylals) of aldehydes - Scope and reactivity of aldehydes with acid anhydrides
-
The geminal diacylates of a variety of aldehydes were prepared in good yields without any catalysts or solvent by simply refluxing the aldehydes with aliphatic acid anhydrides. The scope of the reactions and relative reactivities of aldehydes and acid anhydrides were examined. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
- Rahman, Motiur A. F. M.,Jahng, Yurngdong
-
p. 379 - 383
(2007/10/03)
-
- A remarkable HBF4-SiO2-catalyzed synthesis of acylals from aldehydes under solvent-free conditions
-
HBF4-SiO2 has been found to be an outstanding catalyst for the protection of carbonyl compounds as acylals under entirely solvent-free conditions. Some of the major advantages of this procedure are high yields, ease of operation, high chemoselectivity, high atom efficiency, and compatibility with other protecting groups. Georg Thieme Verlag Stuttgart.
- Kamble, Vinod T.,Bandgar, Babasaheb P.,Joshi, Neeta S.,Jamode, Vasant S.
-
p. 2719 - 2722
(2008/02/11)
-
- An efficient method for the synthesis of acylals from aldehydes using silica-supported perchloric acid (HClO4-SiO2)
-
The synthesis of acylals from structurally diverse aldehydes has been performed in excellent yields under solvent-free conditions using HClO4-SiO2 as a mild, convenient, reusable, and heterogeneous catalyst. The procedure is operationally simple, environmentally benign and has the advantage of enhanced atom utilization. Furthermore, the catalyst can be recovered simply and reused efficiently a number of times without appreciable loss of activity.
- Kamble, Vinod T.,Jamode, Vasant S.,Joshi, Neeta S.,Biradar, Ankush V.,Deshmukh, Rameshchandra Y.
-
p. 5573 - 5576
(2007/10/03)
-
- An efficient and practical procedure for preparation of gem-diacetates from aldehydes catalysed by magnesium perchlorate
-
A mild and efficient method for the preparation of grem-diacetates from aldehydes with acetic anhydride is described using a catalytic amount of magnesium perchlorate giving excellent yields under solvent-free conditions.
- Yang, Shu-Tao
-
p. 199 - 202
(2007/10/03)
-
- Simple synthesis of geminal diacetates (Acylals) of aromatic aldehydes
-
The geminal diacetates of aromatic aldehydes were prepared from corresponding aldehydes by refluxing with acetic anhydride without any catalysts or even any additional solvent. Copyright Taylor & Francis Group, LLC.
- Rahman, Motiur A. F. M.,Jahng, Yurngdong
-
p. 1213 - 1220
(2007/10/03)
-
- A simple and efficient method for the synthesis of gem-diacetates from aldehydes and ketones catalysed by gallium triiodide
-
Aldehydes or ketones reacted with acetic anhydride in dichloromethane at ambient temperature to produce gem-diacetates in good to excellent yields in the presence of gallium triiodide, which was generated in situ from gallium and iodine. This catalyst was also useful for the deprotection of carbonyl compounds in the presence of water.
- Sun, Peipei,Hu, Zhixin
-
p. 659 - 660
(2007/10/03)
-
- Indium tribromide as a highly efficient and versatile catalyst for chemoselective synthesis of acylals from aldehydes under solvent-free conditions
-
A mild and efficient method has been developed for the chemoselective preparation of acylals from aldehydes in the presence of catalytic amounts (0.01-1.0 mol%) of InBr3 under solvent-free conditions in very good to excellent yields.
- Yin, Liang,Zhang, Zhan-Hui,Wang, Yong-Mei,Pang, Mei-Li
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p. 1727 - 1730
(2007/10/03)
-
- Copper(II) tetrafluoroborate-catalyzed formation of aldehyde-1,1-diacetates
-
Aldehyde 1,1-diacetates are farmed in excellent yields from aldehydes and acetic anhydride under solvent-free conditions at room temperature in short times in the presence of a catalytic amount of copper(II) tetrafluoroborate hydrate.
- Chakraborti, Asit K.,Thilagavathi, Ramasamy,Kumar, Raj
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p. 831 - 833
(2007/10/03)
-
- Pharmaceutical compositions
-
Pharmaceutical compositions which are useful for the treatment of cancer or illnesses which arise due to an abnormally elevated cell proliferation comprise acyl derivatives of aromatic aldehydes, especially arylidene diesters and α-alkoxyarylidene esters of general formula (I). STR1
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