18020-59-2Relevant academic research and scientific papers
Acceleration of the Baylis-Hillman reaction in the presence of ionic liquids
Kim, Eun Jin,Ko, Soo Y.,Song, Choong Eui
, p. 894 - 899 (2003)
The Baylis-Hillman reaction is accelerated in the presence of ionic liquids. Of various 1-butyl-3-methylimidazolium (bmim)-based ionic liquids tested, [bmim][PF6] has been found to result in the highest rate increase. In the company of Lewis ac
Salt effects on the Baylis-Hillman reaction
Kumar, Anil,Pawar, Sanjay S.
, p. 5019 - 5026 (2003)
The Baylis-Hillman reaction is shown to accelerate in salt solutions of water and the 'water-like' structured solvents, like formamide and N-methylformamide in the presence of DABCO. Ethylene glycol, another structured solvent and its salt solutions fail
Studies on Pumiliotoxin A Alkaloids: An Approach to Preparing the Indolizidinic Core by Intramolecular Diastereoselective N-Heterocyclic Carbene Catalyzed Benzoin Reaction
Correia, José Tiago M.,Acconcia, Laís V.,Coelho, Fernando
, p. 1972 - 1976 (2016)
In this article, we describe the development of a convergent organocatalytic strategy to prepare the indolizidinic core of the pumiliotoxin A alkaloid family. The key step of the proposed strategy is based on a diastereoselective N-heterocyclic carbene ca
Selenonium ionic liquid as efficient catalyst for the Baylis-Hillman reaction
Lenard?o, Eder J.,Feijó, Josiane de Oliveira,Thurow, Samuel,Perin, Gelson,Jacob, Raquel G.,Silveira, Claudio C.
, p. 5215 - 5217 (2009)
The new acidic ionic liquid phenyl butyl ethyl selenonium tetrafluoroborate, [pbeSe]BF4, was successful used as a co-catalyst in the Baylis-Hillman reaction of aldehydes and electron-deficient alkenes. The Baylis-Hillman adducts were obtained i
Kinetic and mechanistic investigations of the Baylis-Hillman reaction in ionic liquids
Singh, Anshu,Kumar, Anil
, p. 2994 - 3004 (2015)
We report here a quantitative study of the kinetics and mechanism of the Baylis-Hillman reaction in the presence of ionic liquids as solvent media. Apparently, a simple Baylis-Hillman reaction can occur by two different exclusive mechanisms in ionic liquids. The delicate balance of these mechanisms is maintained by the ionic environment employed. The main features of the possible mechanism have been described here along with interesting kinetic consequences. The measurement of rate constants and activation energy parameters demonstrate that as the medium becomes basic, the order of the reaction changes from 1 to 2. An unexpected change in the mechanism of the reaction is observed with a change in the nature of the ionic liquid. The Linear Solvation Energy Relationship has also been used as an investigating tool to delineate the respective contributions of the cation and anion of the ionic liquid. The observation strongly dictates the dependency of the mechanism of the Baylis-Hillman reaction on the nature of the anion of the ionic liquids undertaken for this study.
An Improved Protocol for the Morita-Baylis-Hillman Reaction Allows Unprecedented Broad Synthetic Scope
Amarante, Giovanni W.,Camilo, Nilton S.,Carpanez, Arthur G.,Coelho, Fernando,Fernandes, Fábio S.,Lima, Samia R.,Rodrigues, Manoel T.,Santos, Hugo,Serafim, José Cláudio,Silva, Thiago S.,Zeoly, Lucas A.,de Oliveira, Aline S. B.
supporting information, (2022/01/22)
The Morita-Baylis-Hillman (MBH) reaction has been stablished as an important C?C bond-forming transformation between carbonyl-containing compounds and activated olefins. However, the slow reaction rate usually observed with electron-rich electrophilic par
β,γ-Diaryl α-methylene-γ-butyrolactones as potent antibacterials against methicillin-resistant Staphylococcus aureus
Abutaleb, Nader S.,Hamann, Henry J.,Pal, Rusha,Ramachandran, P. Veeraraghavan,Seleem, Mohamed N.
supporting information, (2020/10/02)
A selected series of racemic α-methylene-γ-butyrolactones (AMGBL) synthesized via allylboration or allylindation reactions were screened against methicillin-resistant Staphylococcus aureus (MRSA) USA300. Unlike natural AMGBLs, such as parthenolide, synthe
Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-Triazoles and regiospecific access to bromomethylcoumarins from Morita-Baylis-Hillman adducts
Karthikeyan, Soundararajan,Shobana, Radha Krishnan,Subimol, Kamarajapurathu Raju,Helen Ratna Monica,Kumar, Ayyanoth Karthik Krishna
, p. 1579 - 1587 (2020/09/16)
The direct transformation of Morita-Baylis-Hillman (MBH) adducts into molecules of interest is a crucial process wherein allylic hydroxy-protected or halogenated MBH adducts are commonly preferred. Herein, we report an azidophosphonium salt (AzPS)-catalys
Asymmetric synthesis of multifunctional aryl allyl ethers by nucleophilic catalysis
Zhao, Shuai,Jin, Lei,Chen, Zhi-Li,Rui, Xue,He, Jia-Yi,Xia, Ran,Chen, Ke,Chen, Xiang-Xiang,Yin, Zi-Jian,Chen, Xin
, p. 11585 - 11588 (2019/04/25)
Asymmetric allylic substitution of Morita-Baylis-Hillman (MBH) carbonates with less-nucleophilic phenols mediated by nucleophilic amine catalysis was successfully developed. A variety of substituted aryl allyl ethers were afforded with moderate to high yields with excellent enantioselectivities. The chiral MBH alcohol could be easily accessed from the corresponding aryl allyl ether.
TiO2@UiO-68-CIL: A Metal-Organic-Framework-Based Bifunctional Composite Catalyst for a One-Pot Sequential Asymmetric Morita-Baylis-Hillman Reaction
Hu, Yu-Hong,Liu, Cong-Xue,Wang, Jian-Cheng,Ren, Xiu-Hui,Kan, Xuan,Dong, Yu-Bin
supporting information, p. 4722 - 4730 (2018/10/24)
A chiral ionic liquid (CIL) moiety of a l-pyrrolidin-2-ylimidazole-decorated homochiral UiO-68-type metal-organic framework, UiO-68-CIL (1), was successfully prepared by the combination of a new premodified chiral CIL ligand (H2L-CIL) and ZrCl4 via a solvothermal method. The TiO2-loaded TiO2@UiO-68-CIL (2) was prepared by impregnating 1 in a toluene solution of Ti(OPri)4 and sequential in situ hydrolysis. The obtained 2 can be a bifunctional asymmetric heterogeneous catalyst to successfully promote the one-pot Morita-Baylis-Hillman reaction starting from aromatic alcohols in a tandem way.
