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Pd‐Catalyzed [2+2+1] Coupling of Alkynes and Arenes: Phenol Diazonium Salts as Mechanistic Trapdoors
Author(s) -
Schmidt Bernd,
Berger René,
Kelling Alexandra,
Schilde Uwe
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100609
Subject(s) - phenol , chemistry , catalysis , medicinal chemistry , oxidative coupling of methane , crystal structure , coupling reaction , polymer chemistry , organic chemistry
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.
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