6283-77-8Relevant academic research and scientific papers
Acylation of Phenols, Alcohols, Thiols, Amines and Aldehydes Using Sulfonic Acid Functionalized Hyper-Cross-Linked Poly(2-naphthol) as a Solid Acid Catalyst
Kalla, Reddi Mohan Naidu,Reddy, Sirigireddy Sudharsan,Kim, Il
, p. 2696 - 2705 (2019/05/28)
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.].
Microwave-assisted green synthesis of 1,1-diacetates (acylals) using selectfluor as an environmental-friendly catalyst under solvent-free conditions
Rezayati, Sobhan,Hajinasiri, Rahimeh,Erfani, Zahra
, p. 2567 - 2576 (2016/03/16)
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.
Tungstosulfonic acid as an efficient solid acid catalyst for acylal synthesis for the protection of the aldehydic carbonyl group
Kalla, Reddi Mohan Naidu,Kim, Mi Ri,Kim, Yu Na,Kim, Il
supporting information, p. 687 - 693 (2016/01/12)
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.
Green procedures for the chemoselective synthesis of acylals and their cleavage promoted by recoverable sulfonic acid based nanoporous carbon (CMK-5-SO3H)
Zareyee, Daryoush,Mirzajanzadeh, Ehsan,Khalilzadeh, Mohammad Ali
, p. 1229 - 1234 (2015/10/06)
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.]
Phospho sulfonic acid as an efficient and recyclable solid acid catalyst for the solvent-free preparation of acylals
Kalla, Reddi Mohan Naidu,Park, Huiju,Hoang, Trinh Thi Kim,Kim, Il
supporting information, p. 5373 - 5376 (2015/01/09)
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
Chemoselective synthesis of geminal diacetates (acylals) using eco-friendly reusable propylsulfonic acid based nanosilica (SBA-15-Ph-PrSO3H) under solvent-free conditions
Zareyee, Daryoush,Moosavi, Sayed M.,Alaminezhad, Alireza
, p. 227 - 231 (2013/08/23)
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.
Conjugate polymer-supported acid catalysts: An efficient and reusable catalyst for the synthesis of geminal diacetates (acylals) under solvent-free conditions
Nabid, Mohammad Reza,Rezaei, Seyed Jamal Tabatabaei,Abedi, Mahvash
experimental part, p. 191 - 199 (2011/03/18)
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.
Silica phosphoric acid: An efficient and recyclable catalyst for the solvent-free synthesis of acylals and their deprotection in MeOH
Zhang, Fuyi,Liu, Hong,Zhang, Qing-Ju,Zhao, Yu-Fen,Yang, Feng-Ling
experimental part, p. 3240 - 3250 (2010/12/24)
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.
Synthesis of 1,1-diacetates using a new combined catalytic system: Copper p-toluenesulfonate/HOAc
Wang, Min,Song, Zhiguo,Gong, Hong,Jiang, Heng
, p. 961 - 966 (2008/09/17)
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.
Chemoselective synthesis of 1,1-diacetates from aldehydes in the presence of Al(HSO4)3 under mild solvent-free conditions
Mirjalili,Zolfigol,Bamoniri,Amrollahi,Sheikhan
, p. 852 - 854 (2008/03/11)
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.
