Rhenium-catalyzed synthesis of multisubstituted aromatic compounds via C-C single-bond cleavage.
A reaction between a beta-keto ester and an acetylene in the presence of a rhenium complex, [ReBr(CO)3(thf)]2, as a catalyst, provided a 2-pyranone derivative in excellent yield via retro-aldol reaction (C-C single bond cleavage). By adding an acetylene-bearing ester group(s) after the formation of 2-pyranones, an aromatization reaction proceeded and multisubstituted aromatic compounds were obtained in good to excellent yields.
Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Okayama, Japan. kuninobu@cc.okayama-u.ac.jp
Yoichiro
Y
Kuninobu
Hisatsugu
H
Takata
Atsushi
A
Kawata
Kazuhiko
K
Takai
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D012211:Rhenium / Q000737:chemistry*
D000480:Alkynes; D006841:Hydrocarbons, Aromatic; D009942:Organometallic Compounds; D011753:Pyrones; D012211:Rhenium