scholarly journals Catalytic enantioselective synthesis of perfluoroalkyl-substituted β-lactones via a concerted asynchronous [2 + 2] cycloaddition: a synthetic and computational study

2019 ◽  
Vol 10 (24) ◽  
pp. 6162-6173 ◽  
Author(s):  
Diego-Javier Barrios Antúnez ◽  
Mark D. Greenhalgh ◽  
Alexander C. Brueckner ◽  
Daniel M. Walden ◽  
Pilar Elías-Rodríguez ◽  
...  
Keyword(s):  
Computational Study ◽  
Enantioselective Synthesis ◽  
Lewis Base

A study into the Lewis base-catalysed enantioselective synthesis of polyfluorinated β-lactones.

scholarly journals Traversing Steric Limitations by Cooperative Lewis Base/Palladium Catalysis: An Enantioselective Synthesis of α-Branched Esters Using 2-Substituted Allyl Electrophiles

2018 ◽  
Vol 57 (26) ◽  
pp. 7800-7803 ◽  
Author(s):  
Kevin J. Schwarz ◽  
Colin M. Pearson ◽  
Gabriel A. Cintron-Rosado ◽  
Peng Liu ◽  
Thomas N. Snaddon
Keyword(s):  
Palladium Catalysis ◽  
Enantioselective Synthesis ◽  
Lewis Base

scholarly journals On the Bonding Situation in Stannocene and Plumbocene N-Heterocyclic Carbene Complexes

2019 ◽  
Author(s):  
Diego Andrada ◽  
Sergi Danés ◽  
Lisa Wirtz ◽  
Carsten Mueller ◽  
Volker Huch ◽  
...  
Keyword(s):  
Computational Study ◽  
Decomposition Analysis ◽  
Heterocyclic Carbenes ◽  
Lewis Base ◽  
Energy Decomposition Analysis ◽  
Dispersion Interactions ◽  
X Ray Diffraction ◽  
Group 14 ◽  
Carbene Complexes ◽  
Covalent Interactions

A detailed experimental and computational study of a series of stannocene and plumbocene N-heterocyclic carbene complexes is presented. This unique class of group 14 Lewis acid base adducts was obtained from reactions of the corresponding metallocenes and N-heterocyclic carbenes (NHC), and were structurally characterized by single crystal X-ray diffraction. The obtained structures show a perpendicular pose of the NHC with respect to the metallocene, hence precluding the maximal interaction between the moieties. The nature of the Sn-CNHC and Pb-CNHC bonds have been investigated by applying Energy Decomposition Analysis (EDA-NOCV). For the sake of comparison, known stannocene and plumbocene Lewis base complexes have been included in the series. The attractive chemical bonding interactions are around 50% electrostatic, 30% covalent and 20% dispersion. Indeed, dispersion interactions play a determining role the bigger the substituents become. The covalent interactions derive from the donation of the carbene ligand into the empty p orbital of the metallocene.

Recent Progress towards Organocatalyzed Asymmetric (Hetero)Arene Formation

Synthesis ◽  
2020 ◽  
Author(s):  
Tingshun Zhu ◽  
Ke Xu ◽  
Ziyuan Wang
Keyword(s):  
Organic Chemistry ◽  
Hydrogen Bonding ◽  
Recent Progress ◽  
De Novo ◽  
Short Review ◽  
Enantioselective Synthesis ◽  
Lewis Base ◽  
Environmentally Benign ◽  
Tertiary Phosphine ◽  
Target Molecules

AbstractOwing to the importance of arene moieties in organic chemistry, methods for arene construction attract great attention. Besides the traditional substitution strategy from pre-existing arenes, the straightforward formation of arene cores can also provide significant shortcuts towards a wide array of target molecules with different substitution patterns. Among direct arene formation reactions, applying environmentally benign organocatalysis to access arene moieties continues to attract increasing attention. This short review provides a brief summary of recent progress on organocatalyzed de novo (hetero)arene formation and applications in enantioselective synthesis.1 Introduction2 Arene Formation with Non-Covalent Organocatalysts2.1 Arene Formation with Acid Organocatalysts2.2 Arene Formation with Base Organocatalysts2.3 Arene Formation with Hydrogen-Bonding Organocatalysts3 Arene Formation with Covalent Organocatalysts3.1 Arene Formation with Lewis Base Organocatalysts3.1.1 Arene Formation with Secondary Amine Organocatalysts3.1.2 Arene Formation with Tertiary Amine, Tertiary Phosphine and Sulfide Organocatalysts3.1.3 Arene Formation with N-Heterocyclic Carbene Organocatalysts3.2 Arene Formation with Lewis Acid Organocatalysts4 Conclusion

Exchange of Cl+ between Lone-Pair Donors and π-Donors: A Computational Study

2000 ◽  
Vol 6 (2) ◽  
pp. 153-160 ◽  
Author(s):  
Theis I. Sølling ◽  
Leo Radom
Keyword(s):  
Ab Initio ◽  
Computational Study ◽  
Lone Pair ◽  
Binding Energies ◽  
Lewis Base ◽  
Molecular Orbital Calculations ◽  
Reaction Energy ◽  
Lewis Bases ◽  
Donor Ability ◽  
Reaction Energies

The chemistry of mono-adducts ([Cl–X]+) between Cl+ and a Lewis base (X = NH3, H2O, HF, PH3, H2S or HCl) has been investigated using ab initio molecular orbital calculations at the G2 level. The reactions of such mono-adducts with additional Lewis bases (Y) are found to give [Y–Cl]+ plus X, generally without an intermediate barrier, via a bis-adduct [Y–Cl–X]+. The binding energies of the bis-adduct and the reaction energies are related to the donor properties of the Lewis bases. The reactions between the mono-adducts [Cl–X]+ and the π-donors ethylene and acetylene yield chloriranium and chlorirenium ions, respectively. These reactions proceed via complexes that resemble either the reactants or products depending on the sign of the reaction energy, the latter in turn being determined by the donor ability of the Lewis base. Results for the chlorine systems are compared with those for the corresponding phosphorus systems investigated previously.

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