Superelectrophilic Fe(III)–Ion Pairs as Stronger Lewis Acid Catalysts for (E)-Selective Intermolecular Carbonyl–Olefin Metathesis

2020 ◽  
Vol 22 (8) ◽  
pp. 3155-3160 ◽  
Author(s):  
Haley Albright ◽  
Hannah L. Vonesh ◽  
Corinna S. Schindler
2018 ◽  
Author(s):  
Haley Albright ◽  
Paul S. Riehl ◽  
Christopher C. McAtee ◽  
Jolene P. Reid ◽  
Jacob R. Ludwig ◽  
...  

<div>Catalytic carbonyl-olefin metathesis reactions have recently been developed as a powerful tool for carbon-carbon bond</div><div>formation. However, currently available synthetic protocols rely exclusively on aryl ketone substrates while the corresponding aliphatic analogs remain elusive. We herein report the development of Lewis acid-catalyzed carbonyl-olefin ring-closing metathesis reactions for aliphatic ketones. Mechanistic investigations are consistent with a distinct mode of activation relying on the in situ formation of a homobimetallic singly-bridged iron(III)-dimer as the active catalytic species. These “superelectrophiles” function as more powerful Lewis acid catalysts that form upon association of individual iron(III)-monomers. While this mode of Lewis acid activation has previously been postulated to exist, it has not yet been applied in a catalytic setting. The insights presented are expected to enable further advancement in Lewis acid catalysis by building upon the activation principle of “superelectrophiles” and broaden the current scope of catalytic carbonyl-olefin metathesis reactions.</div>


2018 ◽  
Vol 5 (11) ◽  
pp. 2763-2771 ◽  
Author(s):  
Hao Xu ◽  
Xudong Wang ◽  
Peng Ji ◽  
Haihong Wu ◽  
Yejun Guan ◽  
...  

Sn-Beta zeolites, with high Sn content and smaller crystal size, hydrothermally synthesized in F−-free medium using N-cyclohexyl-N,N-dimethylcyclohexanaminium hydroxide as the structure-directing agent with the assistance of Na+ and seed, are highly active as Lewis acid catalysts.


2003 ◽  
Vol 17 (10) ◽  
pp. 795-799 ◽  
Author(s):  
Yasuo Imakura ◽  
Satoru Nishiguchi ◽  
Akihiro Orita ◽  
Junzo Otera

ChemInform ◽  
2013 ◽  
Vol 44 (40) ◽  
pp. no-no
Author(s):  
Jeanne-Marie Begouin ◽  
Meike Niggemann

1975 ◽  
Vol 53 (4) ◽  
pp. 616-618 ◽  
Author(s):  
Žarko Stojanac ◽  
Robert A. Dickinson ◽  
Nada Stojanac ◽  
Ronald J. Woznow ◽  
Zdenek Valenta

Lewis acid catalysts cause an orientation reversal in the Diels–Alder additions of 2,6-di-methyl-1,4-quinone (1) and toluquinone (12) to 1-substituted 1,3-butadienes and to 1,2- and 1,3-dialkyl dienes. These results are explained by the preferential formation of one reactive quinone–Lewis acid salt.


1993 ◽  
pp. 87-99 ◽  
Author(s):  
T. C. Chung ◽  
A. Kumar ◽  
F. Chen ◽  
J. Stanat

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