Connecting Catalytic Cycles by Organometallic Transformations in situ: Novel Perspectives in Olefin Metathesis

ChemInform ◽  
2006 ◽  
Vol 37 (30) ◽  
Author(s):  
Bernd Schmidt
Keyword(s):  
Olefin Metathesis ◽  
Organometallic Transformations ◽  
Catalytic Cycles

Connecting catalytic cycles by organometallic transformations in situ: Novel perspectives in the olefin metathesis field

2006 ◽  
Vol 78 (2) ◽  
pp. 469-476 ◽  
Author(s):  
Bernd Schmidt
Keyword(s):  
Double Bond ◽  
Olefin Metathesis ◽  
Metathesis Reaction ◽  
Ring Closing Metathesis ◽  
Double Bond Isomerization ◽  
Metathesis Catalyst ◽  
Organometallic Transformations ◽  
Catalytic Cycles

Tandem sequences consisting of an olefin metathesis step and a subsequent non-metathesis reaction become accessible by organometallic transformations of the Ru-carbene species in situ. This contribution highlights some tandem sequences that rely on the conversion of the metathesis catalyst to Ru-hydrides, with special emphasis on the tandem ring-closing metathesis (RCM)-double-bond isomerization sequence.

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>

Combinatorial Screening of an In Situ Generated Library of Tungsten Oxyhalide and Imido Complexes for Olefin Metathesis

2014 ◽  
Vol 16 (10) ◽  
pp. 551-557 ◽  
Author(s):  
Duane R. Romer ◽  
Victor J. Sussman ◽  
Ken Burdett ◽  
Yu Chen ◽  
Kami J. Miller
Keyword(s):  
Olefin Metathesis ◽  
Combinatorial Screening ◽  
Imido Complexes

scholarly journals Synthesis of 1,2-Dihydroquinolines via Hydrazine-Catalysed Ring-Closing Carbonyl-Olefin Metathesis

2019 ◽  
Author(s):  
Yunfei Zhang ◽  
Jae Hun Sim ◽  
Samantha N. Macmillan ◽  
Tristan Lambert
Keyword(s):  
Nitrogen Atom ◽  
Olefin Metathesis ◽  
Catalytic Cycle ◽  
Protecting Group ◽  
Acid Labile

The synthesis of 1,2-dihydroquinolines by the hydrazine-catalysed ring-closing carbonyl-olefin metathesis (RCCOM) of N-prenylated 2-aminobenzaldehydes is reported. Substrates with a variety of substitution patterns are shown, and the compatibility of these conditions with a range of additives is demonstrated. With an acid-labile protecting group on the nitrogen atom, in situ deprotection and autoxidation furnishes quinolines. In comparison to related oxygen-containing substrates, the cycloaddition step of the catalytic cycle is shown to be slower, but the cycloreversion is found to be more facile.

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>

scholarly journals Stereoretentive Olefin Metathesis Made Easy: In Situ Generation of Highly Selective Ruthenium Catalysts from Commercial Starting Materials

2018 ◽  
Vol 20 (21) ◽  
pp. 6822-6826 ◽  
Author(s):  
Daniel S. Müller ◽  
Idriss Curbet ◽  
Yann Raoul ◽  
Jérôme Le Nôtre ◽  
Olivier Baslé ◽  
...  
Keyword(s):  
Olefin Metathesis ◽  
Ruthenium Catalysts ◽  
In Situ Generation

In situ generation of highly active olefin metathesis initiators

2006 ◽  
Vol 691 (24-25) ◽  
pp. 5482-5486 ◽  
Author(s):  
Nele Ledoux ◽  
Bart Allaert ◽  
David Schaubroeck ◽  
Stijn Monsaert ◽  
Renata Drozdzak ◽  
...  
Keyword(s):  
Olefin Metathesis ◽  
Highly Active ◽  
In Situ Generation
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