Convenient synthesis of electron-donating substituted benzonitriles by photolysis of phenyl halides and esters.
Irradiation of electron-donating substituted phenyl halides (fluorides and chlorides) or esters (mesylates, triflates and phosphates) in aqueous MeCN in the presence of KCN gives the corresponding benzonitriles in 48 to 100% yield through an ArSN1 reaction with the intermediacy of a triplet phenyl cation.
Dichiarante
Valentina
V
Department of Organic Chemistry, The University, V. Taramelli 10, 27100, Pavia, Italy.
Fagnoni
Maurizio
M
Albini
Angelo
A
D002384:Catalysis; D004583:Electrons; D004952:Esters / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D010782:Photolysis; D011190:Potassium Cyanide / Q000737:chemistry
D004952:Esters; D006846:Hydrocarbons, Halogenated; D009570:Nitriles; C014356:benzonitrile; D011190:Potassium Cyanide