85337-09-3Relevant academic research and scientific papers
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.
Solvent-free Chemoselective Synthesis of 1,1-diacetates Catalyzed by Iron Zirconium Phosphate
Karimi, Hirbod
, p. 1000 - 1010 (2015/12/01)
In the present study, a mild, rapid, and efficient method for the protection of aldehydes with acetic anhydride (AA) in the presence of iron zirconium phosphate (ZPFe), 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. The catalyst 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-friendly catalyst, chemoselectivity, simple experimental and work-up procedure, solvent-free conditions and only a stoichiometric amount of AA is needed.
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.
Rice husk supported FeCl3 nanoparticles as an efficient and reusable catalyst for the chemoselective 1,1-diacetate protection and deprotection of aldehydes
Shirini, Farhad,Akbari-Dadamahaleh, Somayeh,Mohammad-Khah, Ali
, p. 10 - 17 (2012/10/29)
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.
Polystyrene-supported, Al(OTf)3-catalyzed chemoselective synthesis of acylals from aldehydes
Boroujeni, Kaveh Parvanak
experimental part, p. 277 - 284 (2011/03/20)
Cross-linked polystyrene-supported aluminium triflate [Ps-Al(OTf)3] has been shown to be a mild, efficient, and chemoselective heterogeneous Lewis acid catalyst for acetylation of aldehydes with acetic anhydride. The catalyst can be recovered simply and reused efficiently at least five times without any noticeable loss of catalytic activity. Copyright Taylor & Francis Group, LLC.
Conversion of aldehydes to acylals using acetic anhydride in presence of catalytic amount of Fe(NO3)3.9H2O under solvent-free conditions at room temperature
Khazaei, Ardeshir,Manesh, Abbas Amini,Rostami, Amin,Alavi-Nik, Heidar Ali,Roosta, Zahra Toodeh
experimental part, p. 614 - 616 (2011/12/15)
Fe(NO3)3.9H2O efficiently catalyzed the conversion of aromatic and aliphatic aldehydes to 1,1-diacetates under solvent-free conditions at room temperature. This study reports the use of Fe(NO3)3.9Hsu
SnCl2.2H2O and Ni(OAc)2.4H2O: Efficient heterogeneous inorganic catalysts for the chemoselective synthesis of geminal diacetates (acylal) under solvent-free conditions
Khazaei, Ardeshir,Manesh, Abbas Amini,Alavi-Nik, Heidar Ali,Roosta, Zahra Toodeh
experimental part, p. 627 - 630 (2011/12/15)
SnCl2.2H2O and Ni(OAc)2.4H2O were found to be efficient catalysts for preparation of 1,1-diacetates under solvent-free conditions at room temperature. Easy work-up and low cost are important features from the environmental and economical points of view, are distinct aspects of this research. Very good to exellent yields, short reaction times, non-toxicity and stability of the catalysts are noteworthy advantages of this method.
Chemoselective synthesis of 1,1-diacetates from aldehydes using anhydrous cobalt(II) bromide under solvent-free conditions
Meshram, Gangadhar A.,Patil, Vishvanath D.
experimental part, p. 442 - 449 (2010/04/02)
A mild and efficient method has been developed for the chemoselective preparation of 1,1-diacetates (acylals) from aldehydes catalyzed in the presence of a catalytic amount (0.1mmol) of anhydrous cobalt(II) bromide under solvent-free conditions. The remarkable selectivity under mild and neutral conditions, excellent yields, short reaction time, and easily available and inexpensive catalyst are important features of this method.
Mild and chemoselective synthesis and deprotection of geminal diacetates catalyzed by titanium(IV) halides
Jung, Misuk,Yoon, Jieun,Kim, Hak Sung,Ryu, Jae-Sang
experimental part, p. 2713 - 2720 (2010/10/02)
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.
