A Convenient Method for Preparing Aromatic α,β-Unsaturated Ketones from α,β-Unsaturated Acyl Chlorides and Arylboronic Acids via Suzuki—Miyaura Type Coupling Reaction.

ChemInform ◽  
2004 ◽  
Vol 35 (21) ◽  
Author(s):  
Yoshio Urawa ◽  
Katsutoshi Nishiura ◽  
Shigeru Souda ◽  
Katsuyuki Ogura
Keyword(s):  
Convenient Method ◽  
Coupling Reaction ◽  
Acyl Chlorides ◽  
Unsaturated Ketones ◽  
Arylboronic Acids ◽  
Unsaturated Acyl ◽  
Type Coupling

Acylation du (cyclopropylméthyl)triméthylsilane. Une nouvelle voie d'accès aux énones non conjuguées

1981 ◽  
Vol 59 (5) ◽  
pp. 802-806 ◽  
Author(s):  
M. Grignon-Dubois ◽  
J. Dunoguès ◽  
R. Calas
Keyword(s):  
Saturated Hydrocarbon ◽  
Chloroacetyl Chloride ◽  
Competitive Reaction ◽  
Acyl Chlorides ◽  
Unsaturated Ketones ◽  
Unsaturated Acyl ◽  
Catalytic Role ◽  
Convenient Route ◽  
Allylic Cleavage

Acylation of (cyclopropylmethyl)trimethylsilane using RCOCl/AlCl3 (R: saturated hydrocarbon group) constitutes a mild, convenient route to β,γ-unsaturated ketones free from the conjugated isomers. With α,β-unsaturated acyl chlorides a competitive reaction between the C—H and C—Si allylic cleavage is observed whereas chloroacetyl chloride affords the γ,δ-ethylenic corresponding ketone. A mechanism involving the catalytic role of HCl in the formation of β,γ-unsaturated and chloroketones is proposed.

Eco-friendly Suzuki–Miyaura coupling of arylboronic acids to aromatic ketones catalyzed by the oxime-palladacycle in biosolvent 2-MeTHF

2016 ◽  
Vol 40 (4) ◽  
pp. 3119-3123 ◽  
Author(s):  
Manoj Mondal ◽  
Utpal Bora
Keyword(s):  
Green Chemistry ◽  
Sugar Cane ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aromatic Ketones ◽  
Acyl Chlorides ◽  
Arylboronic Acids ◽  
Cross Coupling Reaction ◽  
Reaction Proceeds ◽  
Aryl Ketones

Oxime-palladacycle catalyzed aerobic cross-coupling reaction of arylboronic acids and acyl chlorides to yield aryl ketones was developed. The reaction proceeds efficiently in 2-MeTHF, which is derived from corncobs, sugar cane, and fulfils the 3rd, 5th and 7th principles of Green Chemistry.

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