- Acylation of Phenols, Alcohols, Thiols, Amines and Aldehydes Using Sulfonic Acid Functionalized Hyper-Cross-Linked Poly(2-naphthol) as a Solid Acid Catalyst
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Abstract: The hyper-cross-linked porous poly(2-naphthol) fabricated by the Friedel–Crafts alkylation of 2-naphthol has been functionalized with sulfonic acid to obtain a solid acid catalyst. The catalyst is applied for the protection of phenol, alcohols, thiols, amines and aldehydes with acetic anhydride at room temperature. The catalytic protection using the new solid acid is featured by achieving high yield at neat condition, needing no aqueous work-up and/or chromatographic separation, and showing excellent recycling efficiency, suggesting the potential of this sulfonated porous polymers as a new protection protocol in a wide range of sustainable chemical reactions. Graphical Abstract: [Figure not available: see fulltext.].
- Kalla, Reddi Mohan Naidu,Reddy, Sirigireddy Sudharsan,Kim, Il
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p. 2696 - 2705
(2019/05/28)
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- Microwave-assisted green synthesis of 1,1-diacetates (acylals) using selectfluor as an environmental-friendly catalyst under solvent-free conditions
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An efficient and simple procedure has been developed for the acetylation of aldehyde by selectfluor [1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane bis(tetrafluoroborate)] as a chemoselective and environmentally friendly catalyst under solvent-free conditions or microwave irradiation. The application of microwave irradiation improved the yields and reduced the reaction times. In this study, selective conversion of aldehydes was observed in the presence of ketones, and the deprotection of 1,1-diacetates has also been achieved using selectfluor in water as green solvent in reflux conditions. The methodology provides synergy of microwave irradiation which offers several advantages such the simple work-up procedure, short reaction time, excellent yields and environmentally benign procedure.
- Rezayati, Sobhan,Hajinasiri, Rahimeh,Erfani, Zahra
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p. 2567 - 2576
(2016/03/16)
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- Tungstosulfonic acid as an efficient solid acid catalyst for acylal synthesis for the protection of the aldehydic carbonyl group
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Tungstosulfonic acid (TSA) has been found to be an efficient solid acid catalyst for the protection of aldehydic carbonyl groups by geminal diacetate (acylal) formation following the nucleophilic addition of acetic anhydride under neat conditions as well as in a solvent. The TSA catalyst is fully characterized by infrared spectroscopy, wide-angle X-ray scattering analysis, and scanning electron microscopy with energy dispersive X-ray spectroscopy. The deprotection of acylals to corresponding aldehydes has also been investigated under the similar conditions. The catalyst can be reused seven times without a significant loss of activity. In addition, no chromatographic separations are needed to obtain the desired products. This method is a green approach for the chemoselective protection of aldehydes in the presence of ketones.
- Kalla, Reddi Mohan Naidu,Kim, Mi Ri,Kim, Yu Na,Kim, Il
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supporting information
p. 687 - 693
(2016/01/12)
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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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- Phospho sulfonic acid as an efficient and recyclable solid acid catalyst for the solvent-free preparation of acylals
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Phospho sulfonic acid (PSA) acts as a highly effective and reusable catalyst for the chemo-selective protection of aldehydes with acetic anhydride under solvent-free conditions. The desirable features of this new catalytic methodology include its sustaina
- Kalla, Reddi Mohan Naidu,Park, Huiju,Hoang, Trinh Thi Kim,Kim, Il
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supporting information
p. 5373 - 5376
(2015/01/09)
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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
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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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- Conjugate polymer-supported acid catalysts: An efficient and reusable catalyst for the synthesis of geminal diacetates (acylals) under solvent-free conditions
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A comparative study on the catalytic activity of conducting polyaniline (PANI), polypyrrole (PPY), and poly-(3,4-ethylenedioxythiophene) (PEDOT) salts as solid acid catalysts for the synthesis of 1,1-diacetates (acylals) under solvent-free conditions has been presented. Use of the polypyrrole and poly-(3,4-ethylenedioxythiophene) salts as solid acid catalysts is reported for the first time. Preparation, recovery, and reusability of the catalysts were found to be good. Copyright Taylor & Francis Group, LLC.
- Nabid, Mohammad Reza,Rezaei, Seyed Jamal Tabatabaei,Abedi, Mahvash
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experimental part
p. 191 - 199
(2011/03/18)
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- Silica phosphoric acid: An efficient and recyclable catalyst for the solvent-free synthesis of acylals and their deprotection in MeOH
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Silica phosphoric acid was used as an efficient, mild, and recyclable solid catalyst for the synthesis of acylals from various structurally diverse aldehydes and acetic anhydride under solvent-free conditions. The acylation of aldehydes was highly chemoselective, and no ketone was acylated, which provided a method for the synthesis of acylals from aldehydes in the presence of ketones. Silica phosphoric acid-catalyzed deprotection of acylals to the corresponding aldehydes in MeOH has also been developed with excellent yield. The deprotection of the acylals of aromatic aldehydes took priority over those of aliphatic aldehydes. Copyright Taylor & Francis Group, LLC.
- Zhang, Fuyi,Liu, Hong,Zhang, Qing-Ju,Zhao, Yu-Fen,Yang, Feng-Ling
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experimental part
p. 3240 - 3250
(2010/12/24)
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- Synthesis of 1,1-diacetates using a new combined catalytic system: Copper p-toluenesulfonate/HOAc
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Copper p-toluenesulfonate acetic acid has been established as an efficient combined catalytic system for chemoselective conversion of aldehydes to diacetates in high yields at ambient temperature in short reaction times. For the catalytic system, the amount of copper p-toluenesulfonate reduced to 0.3 mol%. After the reaction, copper p-toluenesulfonate can be easily recovered and reused for at least 10 runs. Copyright Taylor & Francis Group, LLC.
- Wang, Min,Song, Zhiguo,Gong, Hong,Jiang, Heng
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p. 961 - 966
(2008/09/17)
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- VSO4.5H2O: A mild and efficient catalyst for chemo-selective conversion of aldehydes to 1,1-diacetates
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Protection of aliphatic and aromatic aldehydes as 1,1-diacetates using VSO4.5H2O under solvent-free conditions is carried out. The products are obtained in good to excellent yields. Ketones are not affected under these conditions.
- Heravi, Majid M.,Bakhtiari, Khadijeh,Benmorad, Tina,Oskooie, Hossein A.
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p. 273 - 275
(2008/02/10)
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- Preparation of geminal diacylates (acylals) of aldehydes - Scope and reactivity of aldehydes with acid anhydrides
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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
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p. 379 - 383
(2007/10/03)
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- P2O5/Al2O3 as an efficient heterogeneous catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions
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An efficient and chemoselective method for the preparation of acylals from different aldehydes using P2O5/Al2O3 and acetic anhydride under solvent-free conditions.
- Hajipour, Abdol R.,Zarei, Amin,Ruoho, Arnold E.
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p. 2881 - 2884
(2007/10/03)
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- Solvent-free chemoselective synthesis of 1,1-diacetates catalyzed by Cu(NO3)2·3H2O
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1,1-Diacetates have been synthesized by the reaction of a variety of aldehydes with acetic anhydride in the presence of cupric nitrate as catalyst under solvent-free conditions. Ketones were not converted to the corresponding diacetates under these conditions. Copyright Taylor & Francis Group, LLC.
- Heravi, Majid M.,Bakhtiari, Khadijeh,Tehrani, Maryam H.,Oskooie, Hossein A.
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p. 1121 - 1126
(2008/02/01)
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- Chemoselective synthesis of 1,1-diacetates from aldehydes in the presence of Al(HSO4)3 under mild solvent-free conditions
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A novel efficient procedure has been developed for the preparation of acylals in high yields by reaction of the corresponding aldehydes with acetic anhydride in the presence of Al(HSO4)3 as catalyst under mild (room temperature) solvent-free conditions.
- Mirjalili,Zolfigol,Bamoniri,Amrollahi,Sheikhan
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p. 852 - 854
(2008/03/11)
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- Cupric sulfate pentahydrate: A mild and efficient catalyst for the chemoselective synthesis of 1,1-diacetates from aldehydes in a solvent-free system
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Cupric sulfate pentahydrate was found to be an efficient catalyst for the protection of aldehydes as 1,1-diacetates in high yields in a solvent-free system at room temperature. Ketones are not affected under these reaction conditions. Springer-Verlag 2006.
- Heravi, Majid M.,Taheri, Shima,Bakhtiari, Khadijeh,Oskooie, Hossein A.
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p. 1075 - 1078
(2007/10/03)
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- Silica sulfuric acid as an efficient heterogeneous catalyst for the synthesis of 1,1-diacetates under solvent-free conditions
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An efficient method for the preparation of acylals from different aldehydes in the presence of silica sulfuric acid and acetic anhydride under solvent-free conditions is reported. Georg Thieme Verlag Stuttgart.
- Hajipour, Abdol R.,Zarei, Amin,Khazdooz, Leila,Mirjalili, Bi Bi F.,Sheikhan, Nafise,Zahmatkesh, Saeed,Ruoho, Arnold E.
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p. 3644 - 3648
(2007/10/03)
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- An efficient conversion of aldehydes to their corresponding acylals with P2O5/SiO2 under mild condition
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A combination of P2O5 and SiO2 was used for an efficient conversion of aldehydes to their corresponding acylals with excellent yields at room temperature under mild conditions.
- Mirjalili, Bibi Fatemeh,Zolfigol, Mohammad Ali,Bamoniri, Abdolhamid
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- Zinc-metal promoted selective α-haloacylation and gem-bisacylation of alkyl aldehydes in the presence of chlorotrimethylsilane
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Treatment of a mixture of alkyl aldehydes (1) with acid chlorides (2) in the presence of zinc metal powder and a catalytic amount of chlorotrimethylsilane (TMSCl) in dichloromethane brought about highly facile and effective coupling to give selectively th
- Ishino, Yoshio,Mihara, Masatoshi,Takeuchi, Takeshi,Takemoto, Masanobu
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p. 3503 - 3506
(2007/10/03)
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- Facile synthesis of 1,1-diacetates from aldehydes using environmentally benign solid acid catalyst under solvent-free conditions
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Variety of aromatic and aliphatic aldehydes are converted into their 1,1-diacetates in the presence of environmentally benign Mo/TiO 2-ZrO2 solid acid catalyst in good to excellent yields under solvent-free conditions.
- Reddy, Benjaram M.,Sreekanth, Pavani M.,Khan, Ataullah
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p. 1839 - 1845
(2007/10/03)
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- Zinc tetrafluoroborate-catalyzed efficient conversion of aldehydes to geminal diacetates and cyanoacetates
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A trace of an aqueous solution of zinc tetrafluoroborate was demonstrated to catalyze the conversion of an aldehyde to its 1,1-diacetate by acetic anhydride without any solvent. A similar reaction of an aldehyde with a mixture of potassium cyanide and acetic anhydride in methylene chloride was also catalyzed by Zn(BF4)2 to provide the corresponding geminal cyanoacetate.
- Ranu, Brindaban C.,Dutta, Jyotirmoy,Das, Arijit
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p. 366 - 367
(2007/10/03)
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- LiBF4-mediated conversion of aldehydes to gem-diacetates
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An efficient and highly selective method for the conversion of aldehydes to gem-diacetates is described using lithium tetrafluoroborate under mild reaction conditions. Due to the neutral reaction conditions, this method is compatible with acid-sensitive p
- Yadav, Jhillu S.,Reddy, Basi V. S.,Venugopal, Chenna,Ramalingam
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p. 604 - 606
(2007/10/03)
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- An efficient synthesis of diacetates from aldehydes using beta zeolite
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A variety of aldehydes react with acetic anhydride in the presence of catalytic amount of β zeolite to afford the corresponding 1,1 diacetates in good to excellent yields.
- Kumar, Pradeep,Hegde, Vishnumurthy R.,Kumar, T. Pavan
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p. 601 - 602
(2007/10/02)
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