Hypervalent iodine oxidation of silyl enol ethers. A direct route to α-hydroxy ketones

1987 ◽  
pp. 1781-1784 ◽  
Author(s):  
Robert M. Moriarty ◽  
Michael P. Duncan ◽  
Om Prakash
Keyword(s):  
Hypervalent Iodine ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Direct Route ◽  
Hydroxy Ketones

ChemInform Abstract: Umpolung Strategy for Synthesis of β-Ketonitriles Through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers.

ChemInform ◽  
2015 ◽  
Vol 46 (48) ◽  
pp. no-no
Author(s):  
Hang Shen ◽  
Jiaqiang Li ◽  
Qing Liu ◽  
Jing Pan ◽  
Ruofeng Huang ◽  
...  
Keyword(s):  
Hypervalent Iodine ◽  
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.

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