Efficient synthesis of dibenzo[a,c]cyclohepten-5-ones via a sequential Suzuki-Miyaura coupling and aldol condensation reaction.
A common strategy for the synthesis of a 7-membered-ring system with a Suzuki-Miyaura coupling followed by an acid/base-promoted intramolecular aldol condensation reaction has been developed. The reaction of 2'-bromoacetophenones with 2-formylphenylboronic acids in the presence of Pd(OAc)(2) and CataCXium PIntB L8 efficiently provided biaryl compounds, which were transformed to a wide array of dibenzo[a,c]cyclohepten-5-ones in excellent yields by a sequential treatment with p-TsOH, followed by 10% aq NaOH.
Bioorganic Science Division, Korea Research Institute of Chemical Technology, Daejeon 305-600, Republic of Korea.
Young Lok
YL
Choi
Chan-Mo
CM
Yu
Bum Tae
BT
Kim
Jung-Nyoung
JN
Heo
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D003508:Cycloheptanes / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands
D000447:Aldehydes; D003508:Cycloheptanes; D008024:Ligands; C116609:3-hydroxybutanal