64002-52-4Relevant academic research and scientific papers
Application of poly(Vinylbenzyltrimethylammonium tribromide) resin as an efficient polymeric catalyst in the acetalization and diacetylation of benzaldehydes
Han, Bingbing,Hu, Junjun,Li, Xianwei,Zheng, Zubiao
supporting information, p. 287 - 293 (2021/04/28)
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.
Transition-Metal-Free Synthesis of Polyfunctional Triarylmethanes and 1,1-Diarylalkanes by Sequential Cross-Coupling of Benzal Diacetates with Organozinc Reagents
Wei, Baosheng,Ren, Qianyi,Bein, Thomas,Knochel, Paul
supporting information, p. 10409 - 10414 (2021/03/26)
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.
The studies on chemoselective promiscuous activity of hydrolases on acylals transformations
Koszelewski, Dominik,Ostaszewski, Ryszard
, (2019/02/27)
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.
Chemoselective synthesis of 1,1-diacetates under solvent-free condition using efficient heterogeneous ecofriendly catalyst: P2O5/kaolin
Rai, Nityanand,Sharma, Abha
, p. 340 - 344 (2019/05/21)
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.
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
Rostami, Amin,Tahmasbi, Bahman,Abedi, Fatemeh
, p. 3689 - 3701 (2016/04/05)
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.
Zinc zirconium phosphate as an efficient catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions
Hajipour, Abdol R,Karimi, Hirbod
, p. 1945 - 1955 (2015/12/30)
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.
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.]
Sulfonated rice husk ash (RHA-SO3H): A highly powerful and efficient solid acid catalyst for the chemoselective preparation and deprotection of 1,1-diacetates
Shirini, Farhad,Mamaghani, Manouchehr,Seddighi, Mohadeseh
, p. 31 - 37 (2013/06/26)
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.
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.
Solvent-free catalytic preparation of 1,1-diacetates using a silica-supported functional ionic liquid as catalyst
Kang, Li Q.,Cai, Yue Q.,Cheng, Lin
, p. 247 - 249 (2013/07/27)
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.
