Electrochemical α-Arylation of Ketones via Anodic Oxidation of In Situ Generated Silyl Enol Ethers

2021 ◽  
Author(s):  
Wolfgang Jud ◽  
Florian Sommer ◽  
C. Oliver Kappe ◽  
David Cantillo
Keyword(s):  
Anodic Oxidation ◽  
Enol Ethers ◽  
Silyl Enol Ethers

ChemInform Abstract: One-Pot Reaction of Unstable N-Acyl Quaternary Salt of Thiazoles or Imidazoles with Silyl Enol Ethers Formed in situ.

ChemInform ◽  
2010 ◽  
Vol 30 (28) ◽  
pp. no-no
Author(s):  
Takashi Itoh ◽  
Michiko Miyazaki ◽  
Kazuhiro Nagata ◽  
Yuji Matsuya ◽  
Akio Ohsawa
Keyword(s):  
Quaternary Salt ◽  
One Pot ◽  
Enol Ethers ◽  
Silyl Enol Ethers

scholarly journals Direct C–H Alpha Arylation of Enones with ArI(O2CR)2 Reagents

2019 ◽  
Author(s):  
Felipe Cesar Sousa e Silva ◽  
Nguyen T Van ◽  
Sarah Wengryniuk
Keyword(s):  
Claisen Rearrangement ◽  
Bond Formation ◽  
Hypervalent Iodine ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Metal Free ◽  
Wide Range ◽  
Reaction Proceeds ◽  
Mechanistic Investigations

Herein, we report the metal-free direct C–H arylation of enones mediated by hypervalent iodine reagents. The reaction proceeds via a reductive iodonium Claisen rearrangement of <i>in situ </i>b-pyridinium silyl enol ethers. The aryl groups are derived from ArI(O<sub>2</sub>CCF<sub>3</sub>)<sub>2</sub> reagents, which are readily accessed from the parent iodoarenes. It is tolerant of a wide range of substitution patterns and the incorporated arenes maintain the valuable iodine functional handle. Mechanistic investigations implicate arylation via an umpoled “enolonium” species and that the presence of a b-pyridinium moiety is critical for desired C–C bond formation.

One Pot Reaction of Unstable N-Acyl Quaternary Salt of Thiazoles or Imidazoles with Silyl Enol Ethers Formed in situ

Heterocycles ◽  
1999 ◽  
Vol 50 (2) ◽  
pp. 667 ◽  
Author(s):  
Akio Ohsawa ◽  
Takashi Itoh ◽  
Michiko Miyazaki ◽  
Kazuhiro Nagata ◽  
Yûji Matsuya
Keyword(s):  
Quaternary Salt ◽  
One Pot ◽  
Enol Ethers ◽  
Silyl Enol Ethers

scholarly journals Direct C–H Alpha Arylation of Enones with ArI(O2CR)2 Reagents

2019 ◽  
Author(s):  
Felipe Cesar Sousa e Silva ◽  
Nguyen T Van ◽  
Sarah Wengryniuk
Keyword(s):  
Claisen Rearrangement ◽  
Bond Formation ◽  
Hypervalent Iodine ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Metal Free ◽  
Wide Range ◽  
Reaction Proceeds ◽  
Mechanistic Investigations

Herein, we report the metal-free direct C–H arylation of enones mediated by hypervalent iodine reagents. The reaction proceeds via a reductive iodonium Claisen rearrangement of <i>in situ </i>b-pyridinium silyl enol ethers. The aryl groups are derived from ArI(O<sub>2</sub>CCF<sub>3</sub>)<sub>2</sub> reagents, which are readily accessed from the parent iodoarenes. It is tolerant of a wide range of substitution patterns and the incorporated arenes maintain the valuable iodine functional handle. Mechanistic investigations implicate arylation via an umpoled “enolonium” species and that the presence of a b-pyridinium moiety is critical for desired C–C bond formation.

scholarly journals Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters

2011 ◽  
Vol 7 ◽  
pp. 648-652 ◽  
Author(s):  
Haruo Aikawa ◽  
Tetsuro Kaneko ◽  
Naoki Asao ◽  
Yoshinori Yamamoto
Keyword(s):  
Alkylating Agents ◽  
Gold Catalyst ◽  
Nucleophilic Attack ◽  
Enol Ether ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Silyl Enol Ether ◽  
Leaving Groups ◽  
Acid Esters

Unprecedented alkylation of silyl enol ethers has been developed by the use of ortho-alkynylbenzoic acid alkyl esters as alkylating agents in the presence of a gold catalyst. The reaction probably proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack on the silyl enol ethers. The generated leaving compound abstracts a proton to regenerate the silyl enol ether structure.

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