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Carbonylative Suzuki–Miyaura Coupling Reaction of Lactam‐, Lactone‐, and Thiolactone‐Derived Enol Triflates for the Synthesis of Unsymmetrical Dienones
Author(s) -
Bartali Laura,
Guarna Antonio,
Larini Paolo,
Occhiato Ernesto G.
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200601089
Subject(s) - chemistry , enol , ketene , catalysis , conjugate , acetal , organic chemistry , coupling reaction , lactam , thioacetal , carbonylation , medicinal chemistry , carbon monoxide , mathematical analysis , mathematics
A thorough study of the carbonylative Suzuki–Miyaura cross‐coupling reaction of enol triflates with alkenylboronic acids for the synthesis of unsymmetrical dienones is reported. Conditions were found that enabled the coupling of structurally different enol triflates derived from lactams, lactones, and thiolactones (i.e., cyclic ketene aminal, acetal, and thioacetal triflates, respectively) with various alkenylboronic acids at room temperature under 1 atm of CO pressure with 1–5 % palladium catalyst; the carbonylated products were obtained in 50–86 % overall yields. The methodology allows for a convergent and rapid preparation of substrates useful in conjugate additions and Nazarov reactions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)