scholarly journals Ionic-Liquid-Mediated MacMillan’s Catalyst for Diels-Alder Reaction

2013 ◽  
Vol 2013 ◽  
pp. 1-5 ◽  
Author(s):  
Vivek Srivastava
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Ionic liquids were used to enhance as well as recycle the MacMillan's catalyst1for the Diels-Alder reaction. Using our developed protocol, Diels-Alder adducts were obtained in good yields and selectivities along the 6 times recycling of MacMillan's imidazolidinone catalyst1. Synthesis of steroid4is the major outcome of our developed protocol.

scholarly journals Ionic liquid promoted Diels-Alder Reaction between anthrone and maleimides

2010 ◽  
Vol 8 (2) ◽  
pp. 356-360 ◽  
Author(s):  
Nitin Mirgane ◽  
Sandip Kotwal ◽  
Anil Karnik
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Room Temperature ◽  
Alder Reaction ◽  
Dual Role ◽  
Diels Alder ◽  
Environmentally Benign ◽  
Green Solvents ◽  
Imidazolium Ionic Liquid ◽  
Diels Alder Reaction

AbstractIonic liquids (IL) are gaining importance as green solvents. Imidazolium ionic liquid [bmim]+[Cl]−, an environmentally benign solvent, was found to promote the Diels-Alder reaction between anthrone and maleimides at room temperature with excellent yields. The ionic liquid played a dual role as solvent and catalyst.

scholarly journals Ionic liquid binary mixtures: how different factors contribute to determine their effect on the reactivity

RSC Advances ◽  
2016 ◽  
Vol 6 (93) ◽  
pp. 90165-90171 ◽  
Author(s):  
Salvatore Marullo ◽  
Francesca D'Anna ◽  
Paola R. Campodonico ◽  
Renato Noto
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Binary Mixtures ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Liquid Binary Mixtures

We studied how mixing ionic liquids affected the rate of the Diels Alder reaction between 9-anthracenemethanol and N-ethylmaleimide.

scholarly journals Accurate Diels-Alder Energies and Endo Selectivity in Ionic Liquids Using the OPLS-VSIL Force Field

2020 ◽  
Vol 21 (4) ◽  
pp. 1190 ◽  
Author(s):  
Caroline Velez ◽  
Brian Doherty ◽  
Orlando Acevedo
Keyword(s):  
Free Energy ◽  
Ionic Liquid ◽  
Hydrogen Bonding ◽  
Ionic Liquids ◽  
Transition State ◽  
Force Field ◽  
Reaction Medium ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Our recently developed optimized potentials for liquid simulations-virtual site ionic liquid (OPLS-VSIL) force field has been shown to provide accurate bulk phase properties and local ion-ion interactions for a wide variety of imidazolium-based ionic liquids. The force field features a virtual site that offloads negative charge to inside the plane of the ring with careful attention given to hydrogen bonding interactions. In this study, the Diels-Alder reaction between cyclopentadiene and methyl acrylate was computationally investigated in the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate, [BMIM][PF6], as a basis for the validation of the OPLS-VSIL to properly reproduce a reaction medium environment. Mixed ab initio quantum mechanics and molecular mechanics (QM/MM) calculations coupled to free energy perturbation and Monte Carlo sampling (FEP/MC) that utilized M06-2X/6-31G(d) and OPLS-VSIL gave activation free energy barriers of 14.9 and 16.0 kcal/mol for the endo-cis and exo-cis Diels-Alder reaction pathways, respectively (exptl. ΔH‡ of 14.6 kcal/mol). The endo selectivity trend was correctly predicted with a calculated 73% endo preference. The rate and selectivity enhancements present in the endo conformation were found to arise from preferential hydrogen bonding with the exposed C4 ring hydrogen on the BMIM cation. Weaker electronic stabilization of the exo transition state was predicted. For comparison, our earlier ±0.8 charge-scaled OPLS-2009IL force field also yielded a ΔG‡ of 14.9 kcal/mol for the favorable endo reaction pathway but did not adequately capture the highly organized solvent interactions present between the cation and Diels-Alder transition state.

ChemInform Abstract: Chiral Ionic Liquid Mediated Diels-Alder Reaction Between Anthrone Enolate and Maleimides.

ChemInform ◽  
2010 ◽  
Vol 41 (40) ◽  
pp. no-no
Author(s):  
Nitin A. Mirgane ◽  
Mohammed Hasan H. Akhtar ◽  
Anil V. Karnik
Keyword(s):  
Ionic Liquid ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Chiral Ionic Liquid

Chiral Cationic Pd-Phosphinooxazolidine Catalysts for a Highly Efficient Asymmetric Diels-Alder Reaction in Ionic Liquids

Heterocycles ◽  
2008 ◽  
Vol 76 (1) ◽  
pp. 381 ◽  
Author(s):  
Hiroto Nakano ◽  
Mitsuhiro Takeshita ◽  
Yasuhiro Nishiuchi ◽  
Kouichi Takahashi ◽  
Reiko Fujita ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Highly Efficient ◽  
Diels Alder Reaction

Reactivity and Efficient Recycling of a Chiral Pd-BINAP Catalyst for Catalytic Asymmetric Diels-Alder Reaction in Ionic Liquid

Heterocycles ◽  
2009 ◽  
Vol 77 (2) ◽  
pp. 1323 ◽  
Author(s):  
Hiroto Nakano ◽  
Mitsuhiro Takeshita ◽  
Yasuhiro Nishiuchi ◽  
Yuta Araki ◽  
Reiko Fujita ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Catalytic Asymmetric

scholarly journals Borenium ionic liquids as catalysts for Diels–Alder reaction: tuneable Lewis superacids for catalytic applications

2017 ◽  
Vol 7 (5) ◽  
pp. 1045-1049 ◽  
Author(s):  
K. Matuszek ◽  
S. Coffie ◽  
A. Chrobok ◽  
M. Swadźba-Kwaśny
Keyword(s):  
Catalytic Activity ◽  
Ionic Liquids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Lewis Acidity ◽  
High Catalytic Activity ◽  
Acceptor Number ◽  
Diels Alder Reaction ◽  
Catalytic Applications

Ionic liquids with Lewis superacidic borenium cations were used as catalysts in solvent-less Diels–Alder cycloaddition. The extremely high catalytic activity correlated with the Lewis acidity, expressed as the Gutmann acceptor number.

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