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.
Kuninobu
Yoichiro
Y
Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Okayama, Japan. kuninobu@cc.okayama-u.ac.jp
Takata
Hisatsugu
H
Kawata
Atsushi
A
Takai
Kazuhiko
K
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