Efficient Glycosylation Using In(OTf)3 as a Lewis Acid: Activation of N-Phenyltrifluoroacetimidate or Thioglycosides with Halogenated Reagents or PhIO

2014 ◽  
Vol 43 (6) ◽  
pp. 956-958 ◽  
Author(s):  
Regina M. Salmasan ◽  
Yoshiyuki Manabe ◽  
Yuriko Kitawaki ◽  
Tsung-Che Chang ◽  
Koichi Fukase
Keyword(s):  
Lewis Acid ◽  
Acid Activation

Catalytic Carbonyl-Olefin Metathesis of Aliphatic Ketones: Iron(III) HomoDimers as Lewis Acidic Superelectrophiles

2018 ◽  
Author(s):  
Haley Albright ◽  
Paul S. Riehl ◽  
Christopher C. McAtee ◽  
Jolene P. Reid ◽  
Jacob R. Ludwig ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Acid Activation ◽  
Lewis Acid Catalysts ◽  
Distinct Mode ◽  
Aliphatic Ketones ◽  
Carbon Carbon Bond ◽  
Metathesis Reactions ◽  
Acid Catalyzed

<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>

Efficient Phosphodiester Binding and Cleavage by a ZnII Complex Combining Hydrogen-Bonding Interactions and Double Lewis Acid Activation

2006 ◽  
Vol 45 (42) ◽  
pp. 7056-7059 ◽  
Author(s):  
Guoqiang Feng ◽  
Daniela Natale ◽  
Ravi Prabaharan ◽  
Juan C. Mareque-Rivas ◽  
Nicholas H. Williams
Keyword(s):  
Hydrogen Bonding ◽  
Lewis Acid ◽  
Acid Activation ◽  
Hydrogen Bonding Interactions

Hydrosilylation of Carbonyls Catalyzed by Hydridoborenium Borate Salts: Lewis Acid Activation and Anion Mediated Pathways

2020 ◽  
Vol 59 (10) ◽  
pp. 7195-7203 ◽  
Author(s):  
Sandeep Rawat ◽  
Mamta Bhandari ◽  
Vishal Kumar Porwal ◽  
Sanjay Singh
Keyword(s):  
Lewis Acid ◽  
Acid Activation ◽  
Borate Salts

Ru alkylidene compounds bearing tridentate, dianionic ligands: Lewis acid activation and olefin metathesis

2016 ◽  
Vol 45 (9) ◽  
pp. 3844-3852 ◽  
Author(s):  
Adam M. McKinty ◽  
Douglas W. Stephan
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Acid Activation ◽  
Dianionic Ligands

The series of tridentate complexes were prepared and shown to react with BCl3 to give the complexes affording neutral and cationic complexes sequentially. The generated five coordinate cations were evaluated in standard preliminary tests for olefin metathesis catalysis.

ChemInform Abstract: Lewis Acid Activation of Carbodicarbene Catalysts for Rh-Catalyzed Hydroarylation of Dienes.

ChemInform ◽  
2015 ◽  
Vol 46 (44) ◽  
pp. no-no
Author(s):  
Courtney C. Roberts ◽  
Desiree M. Matias ◽  
Matthew J. Goldfogel ◽  
Simon J. Meek
Keyword(s):  
Lewis Acid ◽  
Acid Activation

Mechanism of Silver-Mediated Geminal Difluorination of Styrenes with a Fluoroiodane Reagent: Insights into Lewis-Acid-Activation Model

2016 ◽  
Vol 18 (23) ◽  
pp. 6128-6131 ◽  
Author(s):  
Biying Zhou ◽  
Taishan Yan ◽  
Xiao-Song Xue ◽  
Jin-Pei Cheng
Keyword(s):  
Lewis Acid ◽  
Acid Activation ◽  
Activation Model

Catalytic Carbonyl-Olefin Metathesis of Aliphatic Ketones: Iron(III) HomoDimers as Lewis Acidic Superelectrophiles

2018 ◽  
Author(s):  
Haley Albright ◽  
Paul S. Riehl ◽  
Christopher C. McAtee ◽  
Jolene P. Reid ◽  
Jacob R. Ludwig ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Acid Activation ◽  
Lewis Acid Catalysts ◽  
Distinct Mode ◽  
Aliphatic Ketones ◽  
Carbon Carbon Bond ◽  
Metathesis Reactions ◽  
Acid Catalyzed

<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>

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