scholarly journals Solid state frustrated Lewis pair chemistry

2018 ◽  
Vol 9 (21) ◽  
pp. 4859-4865 ◽  
Author(s):  
Long Wang ◽  
Gerald Kehr ◽  
Constantin G. Daniliuc ◽  
Melanie Brinkkötter ◽  
Thomas Wiegand ◽  
...  
Keyword(s):  
Solid State ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Frustrated Lewis Pair

In solution the PCy3/B(C6F5)3 pair is rapidly deactivated by nucleophilic aromatic substitution. In the solid state (or in a fluorous liquid), however, it serves as an active frustrated Lewis pair to effectively split dihydrogen.

Bis(pentafluorophenyl)-o-carborane and its arylthio derivatives: synthesis, electrochemistry and optical properties

2020 ◽  
Vol 49 (37) ◽  
pp. 12985-12989
Author(s):  
Naoki Shida ◽  
Satoshi Owaki ◽  
Hiroshi Eguchi ◽  
Takanobu Nishikawa ◽  
Ikuyoshi Tomita ◽  
...  
Keyword(s):  
Optical Properties ◽  
Solid State ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Aggregation Induced Emission

The synthesis of bis(pentafluorophenyl)-o-carborane is reported, which is further thiolated by nucleophilic aromatic substitution (SNAr) reaction to give emissive materials in the solid state following aggregation-induced emission (AIE) fashion.

Zur Reaktion von 2,3-Dihydroimidazol-2-ylidenen mit Pentafluorpyridin: Carbene als Reaktionspartner in der nucleophilen aromatischen Substitution/ On the Reaction of 2,3-Dihydroimidazol-2-ylidenes with Pentafluoropyridine: Carbenes as Reactants in Nucleophilic Aromatic Substitution

1998 ◽  
Vol 53 (8) ◽  
pp. 881-886 ◽  
Author(s):  
Norbert Kuhn ◽  
Joanna Fahl ◽  
Roland Boese ◽  
Gerald Henkel
Keyword(s):  
Solid State ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
X Ray

Abstract The 2,3-dihydro-1,3,4,5-tetraalkylimidazol-2-ylidenes 3 (R = Me, iso-Pr) react immediately with pentafluoropyridine to form the 2-tetrafluoropyridylimidazolium salts 4 in good yields. In contrast with the tetramethyl derivative 4a, alkyl fluoride is eliminated from the isopropyl salt 4b to give 1 -isopropyl-4,5-dimethyl-2-tetrafluoropyridylimidazole, which dimerises via hydrogen bridges in the solid state (7). The X-ray structures of 1,3-diisopropyl-4,5-dimethyl-2-tetrafluoropyridylimidazolium chloride (5) and 7 are reported.

Facile 1,1-Carboboration Reaction of a Diarylphosphino-substituted Conjugated Diyne with Tris(pentafluorophenyl)borane

2013 ◽  
Vol 68 (5-6) ◽  
pp. 666-674 ◽  
Author(s):  
Philipp Feldhaus ◽  
Gerald Kehr ◽  
Roland Fröhlich ◽  
Constantin G. Daniliuc ◽  
Gerhard Erker
Keyword(s):  
Crystal Structure ◽  
Carbon Atom ◽  
Substitution Reaction ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
X Ray ◽  
Frustrated Lewis Pair ◽  
Selective Formation

Bis(dimesitylphosphanyl)butadiyne (14) reacts with B(C6F5)3 by a 1,1-carboboration sequence. The selective attack at a single phosphanyl-alkyne moiety is observed. First a phosphirenium-borate zwitterion 15 is formed at r. t. Thermolysis (80 °C) results in the E-selective formation of the 1,1- carboboration product, the frustrated Lewis pair (FLP) E-16, which upon heating to 160 °C eventually undergoes isomerization followed by an internal nucleophilic aromatic substitution reaction to give the product 17 featuring a -B(F)(C6F5)2 substituent at the five-membered P-heterocycle. Finally, the FLP E-16 was reacted with n-butylisocyanide to yield the five-membered heterocyclic product 18, formed by P,B addition to the isonitrile carbon atom. Compounds 14, 15, 17, and 18 were characterized by X-ray crystal structure analyses

scholarly journals Machine learning meets mechanistic modelling for accurate prediction of experimental activation energies

2021 ◽  
Author(s):  
Kjell Jorner ◽  
Tore Brinck ◽  
Per-Ola Norrby ◽  
David Buttar
Keyword(s):  
Machine Learning ◽  
Activation Energies ◽  
Accurate Prediction ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Mechanistic Modelling

Hybrid reactivity models, combining mechanistic calculations and machine learning with descriptors, are used to predict barriers for nucleophilic aromatic substitution.

Enantioselective Nucleophilic Aromatic Substitution Reaction of Azlactones to Synthesize Quaternary α-Amino Acid Derivatives

Synlett ◽  
2020 ◽  
Author(s):  
Xiaohua Liu ◽  
Yi Li ◽  
Hao Pan ◽  
Wang-Yuren Li ◽  
Xiaoming Feng
Keyword(s):  
Hydrogen Bonding ◽  
Charge Transfer ◽  
Amino Acid ◽  
Substitution Reaction ◽  
Nucleophilic Aromatic Substitution ◽  
Amino Acid Derivatives ◽  
Amino Acid Esters ◽  
Aromatic Substitution ◽  
Charge Transfer Interaction ◽  
Acid Esters

AbstractAn asymmetric organocatalytic nucleophilic aromatic substitution reaction of azlactones with electron-deficient aryls was established. A variety of α-aryl α-alkyl α-amino acid esters and peptides were obtained in decent yields and stereoselectivities. A new bifunctional catalytic mode involving charge-transfer interaction and hydrogen bonding is proposed to explain the enantioselectivity.

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