Pd??Catalyzed [2+ 2+ 1] Coupling of Alkynes and Arenes: Phenol Diazonium Salts as Mechanistic Trapdoors

B Schmidt, R Berger, A Kelling…

Index: Schmidt, Bernd; Berger, Rene; Kelling, Alexandra; Schilde, Uwe Chemistry - A European Journal, 2011 , vol. 17, # 25 p. 7032 - 7040

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Citation Number: 11

Abstract

Abstract Alkynes and phenol diazonium salts undergo a Pd-catalyzed [2+ 2+ 1] cyclization reaction to spiro [4, 5] decatetraene-7-ones. This structure was confirmed for one example by X-ray single-crystal structure analysis. The reaction is believed to proceed through oxidative addition of the phenol diazonium cation to Pd 0, subsequent insertion of two alkynes, followed by irreversible spirocyclization.