Ordered Hydrogen-Bonded Alcohol Networks Confined in Lewis Acid Zeolites Accelerate Transfer Hydrogenation Turnover Rates

2020 ◽  
Vol 142 (45) ◽  
pp. 19379-19392
Author(s):  
John R. Di Iorio ◽  
Blake A. Johnson ◽  
Yuriy Román-Leshkov
Keyword(s):  
Lewis Acid ◽  
Transfer Hydrogenation ◽  
Turnover Rates ◽  
Acid Zeolites ◽  
Hydrogen Bonded

A Continuous Flow Strategy for the Coupled Transfer Hydrogenation and Etherification of 5-(Hydroxymethyl)furfural using Lewis Acid Zeolites

ChemSusChem ◽  
2014 ◽  
Vol 7 (8) ◽  
pp. 2255-2265 ◽  
Author(s):  
Jennifer D. Lewis ◽  
Stijn Van de Vyver ◽  
Anthony J. Crisci ◽  
William R. Gunther ◽  
Vladimir K. Michaelis ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Continuous Flow ◽  
Transfer Hydrogenation ◽  
Hydroxymethyl Furfural ◽  
Acid Zeolites

scholarly journals Reactions of biologically inspired hydride sources with B(C 6 F 5 ) 3

2017 ◽  
Vol 375 (2101) ◽  
pp. 20170009 ◽  
Author(s):  
Lewis C. Wilkins ◽  
Nicolò Santi ◽  
Louis Y. P. Luk ◽  
Rebecca L. Melen
Keyword(s):  
Carboxylic Acid ◽  
Recent Work ◽  
Lewis Acid ◽  
The Other ◽  
Disproportionation Reaction ◽  
Transfer Hydrogenation ◽  
Acid Moiety ◽  
Biologically Inspired ◽  
Strong Lewis Acid ◽  
High Yields

The combination of 1-benzyl-1,4-dihydropyridines with the strong Lewis acid, B(C 6 F 5 ) 3 , generates a stable pyridinium borohydride species in high yields (94%) in as little as 10 min. This use of biologically inspired hydride sources further builds on the recent work of new hydride donors in the formation of borohydrides. When functionalizing the dihydropyridine with an amide or carboxylic acid moiety, a disproportionation reaction composed of a series of protonation/reduction steps is observed upon the addition of B(C 6 F 5 ) 3 . As a result, one equivalent of dihydropyridine undergoes net hydrogenation, whereas the other is dehydrogenated yielding the pyridinium counterpart in a transfer hydrogenation-type mechanism. This article is part of the themed issue ‘Frustrated Lewis pair chemistry’.

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