Azaborines: synthesis and use in the generation of stabilized boron-substituted carbocations

2018 ◽  
Vol 47 (6) ◽  
pp. 1791-1795 ◽  
Author(s):  
J. J. Clarke ◽  
P. Eisenberger ◽  
S. S. Piotrkowski ◽  
C. M. Crudden
Keyword(s):  
Lewis Acids ◽  
Ring Expansion ◽  
Lewis Acidity ◽  
Frustrated Lewis Pairs ◽  
Carbene Insertion ◽  
Hydride Abstraction ◽  
Ring Expansion Reaction ◽  
Lewis Pairs

A formal N-heterocyclic carbene insertion into the B–H bond of 9-BBN followed by a ring expansion reaction is reported. NHC-9-BBN adducts were reacted in one or two steps to give the corresponding di- or triazaborines. Hydride abstraction of selected species with [Ph3C]+ is facile, giving rise to 6π-aromatic cations with Lewis acidity comparable to Lewis acids commonly employed in frustrated Lewis pairs.

scholarly journals Halogenated triphenylgallium and -indium in frustrated Lewis pair activations and hydrogenation catalysis

2017 ◽  
Vol 375 (2101) ◽  
pp. 20170014 ◽  
Author(s):  
Maotong Xu ◽  
Josephine Possart ◽  
Alexander E. Waked ◽  
Julie Roy ◽  
Werner Uhl ◽  
...  
Keyword(s):  
Lewis Acids ◽  
Lewis Acidity ◽  
Frustrated Lewis Pairs ◽  
Frustrated Lewis Pair ◽  
Hydrogenation Catalysis ◽  
Lewis Pairs

The Lewis acids Ga(C 6 F 5 ) 3 , In(C 6 F 5 ) 3 and Ga(C 6 Cl 5 ) 3 are prepared and their Lewis acidity has been probed experimentally and computationally. The species Ga(C 6 F 5 ) 3 and In(C 6 F 5 ) 3 in conjunction with phosphine donors are shown to heterolytically split H 2 and catalyse the hydrogenation of an imine. In addition, frustrated Lewis pairs (FLPs) derived from Ga(C 6 F 5 ) 3 and In(C 6 F 5 ) 3 and phosphines react with diphenyldisulfide to phosphoniumgallates or indates of the form [ t Bu 3 PSPh][PhSE(C 6 F 5 ) 3 ] and [ t Bu 3 PSPh][(μ-SPh)(E(C 6 F 5 ) 3 ) 2 ] (E = Ga, In). The potential of the FLPs based on Ga(C 6 F 5 ) 3 , In(C 6 F 5 ) 3 and Ga(C 6 Cl 5 ) 3 and phosphines is also shown in reactions with phenylacetylene to give pure or mixtures of the products [ t Bu 3 PH][PhCCE(C 6 X 5 ) 3 ] and R 3 P(Ph)C=C(H)E(C 6 X 5 ) 3 . A number of these species are crystallographically characterized. The implications for the use of these species in FLP chemistry are considered. This article is part of the themed issue ‘Frustrated Lewis pair chemistry’.

Frustrated Lewis Pairs Comprising Nitrogen Lewis Acids for Si–H Bond Activation

2020 ◽  
Vol 132 (52) ◽  
pp. 23682-23685
Author(s):  
Idan Avigdori ◽  
Alla Pogoreltsev ◽  
Alexander Kaushanski ◽  
Natalia Fridman ◽  
Mark Gandelman
Keyword(s):  
Lewis Acids ◽  
Bond Activation ◽  
Frustrated Lewis Pairs ◽  
Lewis Pairs

Catalytic Hydrogenation with Frustrated Lewis Pairs: Selectivity Achieved by Size-Exclusion Design of Lewis Acids

2011 ◽  
Vol 18 (2) ◽  
pp. 574-585 ◽  
Author(s):  
Gábor Erős ◽  
Krisztina Nagy ◽  
Hasan Mehdi ◽  
Imre Pápai ◽  
Péter Nagy ◽  
...  
Keyword(s):  
Catalytic Hydrogenation ◽  
Lewis Acids ◽  
Size Exclusion ◽  
Frustrated Lewis Pairs ◽  
Lewis Pairs

Design considerations for chiral frustrated Lewis pairs: B/N FLPs derived from 3,5-bicyclic aryl piperidines

2019 ◽  
Vol 48 (1) ◽  
pp. 133-141 ◽  
Author(s):  
Jolie Lam ◽  
Susanna Sampaolesi ◽  
James H. W. LaFortune ◽  
Jotham W. Coe ◽  
Douglas W. Stephan
Keyword(s):  
Computational Methods ◽  
Lewis Acidity ◽  
Frustrated Lewis Pairs ◽  
Design Considerations ◽  
Acidity And Basicity ◽  
Lewis Pairs

3,5-Bicyclic aryl piperidines are derivatized to generate chiral B/N FLPs. The Lewis acidities were assessed by experimental and computational methods. The activity in HD scrambling and hydrogenation was also assessed. These data demonstrate that a threshold of combined Lewis acidity and basicity is essential to activate H2.

Synthesis and Lewis acidity of fluorophosphonium cations

2015 ◽  
Vol 44 (27) ◽  
pp. 12256-12264 ◽  
Author(s):  
Christopher B. Caputo ◽  
Daniel Winkelhaus ◽  
Roman Dobrovetsky ◽  
Lindsay J. Hounjet ◽  
Douglas W. Stephan
Keyword(s):  
Lewis Acidity ◽  
Frustrated Lewis Pairs ◽  
Lewis Pairs

A series of fluorophosphonium salts, [R3PF][X] (R = alkyl or aryl; X = FB(C6F5)3, [B(C6F5)4]), have been prepared by reactions of phosphine/borane frustrated Lewis pairs (FLPs) with XeF2 or difluorophosphoranes with [Et3Si][B(C6F5)4].

“Inverse” Frustrated Lewis Pairs – Activation of Dihydrogen with Organosuperbases and Moderate to Weak Lewis Acids

2016 ◽  
Vol 138 (10) ◽  
pp. 3286-3289 ◽  
Author(s):  
Suresh Mummadi ◽  
Daniel K. Unruh ◽  
Jiyang Zhao ◽  
Shuhua Li ◽  
Clemens Krempner
Keyword(s):  
Lewis Acids ◽  
Frustrated Lewis Pairs ◽  
Lewis Pairs

Tuning Lewis acidity using the reactivity of “frustrated Lewis pairs”: facile formation of phosphine-boranes and cationic phosphonium-boranes

2007 ◽  
pp. 3407 ◽  
Author(s):  
Gregory C. Welch ◽  
Lourdes Cabrera ◽  
Preston A. Chase ◽  
Emily Hollink ◽  
Jason D. Masuda ◽  
...  
Keyword(s):  
Lewis Acidity ◽  
Frustrated Lewis Pairs ◽  
Lewis Pairs
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