Hydrogenation of cage-opened C60 derivatives mediated by frustrated Lewis pairs

Author(s):  
Yoshifumi Hashikawa ◽  
Yasujiro Murata

Multiply-carbonylated fullerene derivatives were found to work as one component in frustrated Lewis pairs which caused an Si–H bond activation in the presence of B(C6F5)3, leading to the carbonyl hydrogenation in up to 99% yield.

2008 ◽  
Vol 120 (13) ◽  
pp. 2469-2472 ◽  
Author(s):  
Tibor András Rokob ◽  
Andrea Hamza ◽  
András Stirling ◽  
Tibor Soós ◽  
Imre Pápai

2019 ◽  
Vol 48 (9) ◽  
pp. 2896-2899 ◽  
Author(s):  
Petra Vasko ◽  
M. Ángeles Fuentes ◽  
Jamie Hicks ◽  
Simon Aldridge

The interactions of the O–H bonds in alcohols, water and phenol with dimethylxanthene-derived frustrated Lewis pairs (FLPs) have been probed.


2020 ◽  
Vol 132 (52) ◽  
pp. 23682-23685
Author(s):  
Idan Avigdori ◽  
Alla Pogoreltsev ◽  
Alexander Kaushanski ◽  
Natalia Fridman ◽  
Mark Gandelman

2020 ◽  
Vol 49 (4) ◽  
pp. 1319-1324
Author(s):  
Alvaro I. Briceno-Strocchia ◽  
Timothy C. Johnstone ◽  
Douglas W. Stephan

Our interest in C–F bond activation prompted an investigation of the reactions of PhC(O)CF3 with a superbasic proazaphosphatrane (Verkade's base) and a corresponding FLP.


2013 ◽  
Vol 135 (17) ◽  
pp. 6446-6449 ◽  
Author(s):  
Gabriel Ménard ◽  
Jillian A. Hatnean ◽  
Hugh J. Cowley ◽  
Alan J. Lough ◽  
Jeremy M. Rawson ◽  
...  

2020 ◽  
Author(s):  
Jordan N. Bentley ◽  
Ekadashi Pradhan ◽  
Tao Zeng ◽  
Christopher B. Caputo

The understanding of the mechanism by which frustrated Lewis pairs activate small molecules has been evolving with the discovery that both heterolytic and homolytic bond activation is possible. Herein we characterized a novel Lewis acidic aminoborane containing a phenothiazyl substituent and demonstrate its potential to catalytically promote the dehydrocoupling of tin hydrides. The reactivity observed implies this species promotes homolytic bond activation, however computational analysis suggests a heterolytic mechanism for this reaction. This result represents the first frustrated Lewis pair system to blur the lines between heterolytic and homolytic reactivity.


Synthesis ◽  
2021 ◽  
Author(s):  
Frédéric-Georges Fontaine ◽  
Vincent Desrosiers

In the past years, the chemistry of Frustrated Lewis pairs enabled a plethora of transformations that would otherwise only be possible using transition metal catalysts. Of particular interest are the C-H bond activation and borylation reactions, which is the subject of this review. The FLP borylation chemistry is compared with the early borylation methodologies using strongly electrophilic borenium ions. We present the mechanism of the C-H borylation using inter- and intramolecular Lewis pairs, along with some applications of these transformations.


2020 ◽  
Author(s):  
Jordan N. Bentley ◽  
Ekadashi Pradhan ◽  
Tao Zeng ◽  
Christopher B. Caputo

The understanding of the mechanism by which frustrated Lewis pairs activate small molecules has been evolving with the discovery that both heterolytic and homolytic bond activation is possible. Herein we characterized a novel Lewis acidic aminoborane containing a phenothiazyl substituent and demonstrate its potential to catalytically promote the dehydrocoupling of tin hydrides. The reactivity observed implies this species promotes homolytic bond activation, however computational analysis suggests a heterolytic mechanism for this reaction. This result represents the first frustrated Lewis pair system to blur the lines between heterolytic and homolytic reactivity.


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