scholarly journals Sulfoxide synthesis from sulfinate esters under Pummerer-like conditions

2020 ◽  
Vol 56 (40) ◽  
pp. 5429-5432
Author(s):  
Akihiro Kobayashi ◽  
Tsubasa Matsuzawa ◽  
Takamitsu Hosoya ◽  
Suguru Yoshida
Keyword(s):  
Reaction Mechanism ◽  
Synthetic Method ◽  
Sulfinate Esters

A facile synthetic method of allyl sulfoxides by S-allylation of sulfinate esters proceeds through sulfonium intermediates. On the basis of the plausible reaction mechanism, S-alkynylation and S-arylation were also accomplished.

scholarly journals Sulfoxide Synthesis from Sulfinate Esters under Pummerer-like Conditions

2020 ◽  
Author(s):  
Akihiro Kobayashi ◽  
Tsubasa Matsuzawa ◽  
Takamitsu Hosoya ◽  
Suguru Yoshida
Keyword(s):  
Reaction Mechanism ◽  
Sigmatropic Rearrangement ◽  
Synthetic Method ◽  
Sulfonium Salt ◽  
Sulfinate Esters

A facile synthetic method of allyl sulfoxides by <i>S</i>-allylation of sulfinate esters through sulfonium intermediates has been developed without [3,3]-sigmatropic rearrangement and further Pummerer-type reactions of the resulting allyl sulfoxides. On the basis of the plausible reaction mechanism involving sulfonium salt intermediates, S-alkynylation and S-arylation were also accomplished.<br>

scholarly journals Sulfoxide Synthesis from Sulfinate Esters under Pummerer-like Conditions

2020 ◽  
Author(s):  
Akihiro Kobayashi ◽  
Tsubasa Matsuzawa ◽  
Takamitsu Hosoya ◽  
Suguru Yoshida
Keyword(s):  
Reaction Mechanism ◽  
Sigmatropic Rearrangement ◽  
Synthetic Method ◽  
Sulfonium Salt ◽  
Sulfinate Esters

A facile synthetic method of allyl sulfoxides by <i>S</i>-allylation of sulfinate esters through sulfonium intermediates has been developed without [3,3]-sigmatropic rearrangement and further Pummerer-type reactions of the resulting allyl sulfoxides. On the basis of the plausible reaction mechanism involving sulfonium salt intermediates, S-alkynylation and S-arylation were also accomplished.<br>

Synthesis of axially chiral bipyridine N,N'-dioxides and enantioselective allylation of aldehydes

2010 ◽  
Vol 82 (9) ◽  
pp. 1813-1826 ◽  
Author(s):  
Martin Kotora
Keyword(s):  
Reaction Mechanism ◽  
Aromatic Aldehydes ◽  
Synthetic Method ◽  
Chirality Transfer ◽  
Lewis Bases ◽  
Synthetic Strategy ◽  
Axially Chiral

N-oxides possessing the pyridine framework are strong Lewis bases that can activate the C–Si bond of allylhalosilanes to such an extent that they catalyze reactions with aldehydes. N-oxides embedded in chiral scaffolds are usually capable of highly selective chirality transfer to the derived products. Our goal was to develop a general synthetic method allowing the preparation of structurally varied N,N'-dioxides suitable for enantioselective organocatalysis. The underlying synthetic strategy was based on [2 + 2 + 2]-cyclotrimerization of suitably substituted diynes with nitriles catalyzed by Co-complexes to generate the desired bipyridines, their further oxidation and resolution of which furnished the corresponding chiral N,N'-dioxides. The prepared compounds were used in catalytic allylation of aromatic aldehydes to homoallyl alcohols with high enantioselectivity (up to 96 % ee). Enantioselectivity, enantiodiscrimination, and the reaction mechanism are controlled by the choice of solvent.

Arylation of enelactams using TIPSOTf: reaction scope and mechanistic insight

2021 ◽  
Author(s):  
Tomasz J. Idzik ◽  
Zofia M. Myk ◽  
Łukasz Struk ◽  
Magdalena Perużyńska ◽  
Gabriela Maciejewska ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Multinuclear Nmr ◽  
Mechanistic Insight ◽  
Nmr Study ◽  
Wide Range

Triisopropylsilyltrifluoromethanesulfonate can be effectively used for the arylation of a wide range of enelactams. The multinuclear NMR study provided deep insights into the reaction mechanism.

Theoretical study of the ketonization reaction mechanism of acetic acid over SiO2

2009 ◽  
Author(s):  
Mendel Fleisher ◽  
E. Lukevics ◽  
L. Leite ◽  
D. Jansone ◽  
K. Edolfa ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Reaction Mechanism ◽  
Theoretical Study

OPTIMIZATION OF A SURROGATE REDUCED AVIATION FUEL-AIR REACTION MECHANISM USING A GENETIC ALGORITHM

Clean Air ◽  
2007 ◽  
Vol 8 (1) ◽  
pp. 1-24
Author(s):  
M. Pourkashanian ◽  
N. S. Mera ◽  
Lionel Elliott ◽  
C. W. Wilson ◽  
Derek B. Ingham ◽  
...  
Keyword(s):  
Genetic Algorithm ◽  
Reaction Mechanism ◽  
Aviation Fuel

Ligand-Enabled γ-C(sp3)–H Olefination of Free Carboxylic Acids

2020 ◽  
Author(s):  
Kiron Kumar Ghosh ◽  
Alexander Uttry ◽  
Francesca Ghiringhelli ◽  
Arup Mondal ◽  
Manuel van Gemmeren
Keyword(s):  
Reaction Mechanism ◽  
Carboxylic Acids ◽  
Michael Addition ◽  
Kinetic Studies ◽  
Wide Range ◽  
Palladium Catalyzed

We report the ligand enabled C(sp3)–H activation/olefination of free carboxylic acids in the γ-position. Through an intramolecular Michael-addition, δ-lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium-catalyzed activation of free carboxylic acids in the γ-position. The developed protocol features a wide range of acid substrates and olefin reaction partners and is shown to be applicable on a preparatively useful scale. Insights into the underlying reaction mechanism obtained through kinetic studies are reported.<br>

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