Manganese-catalyzed construction of tetrasubstituted benzenes from 1,3-dicarbonyl compounds and terminal acetylenes.
Treatment of beta-keto esters with terminal acetylenes in the presence of a catalytic amount of a manganese complex, MnBr(CO)5, and molecular sieves, gave multisubstituted aromatic compounds in good to excellent yields. This reaction employs [2 + 2 + 2] cycloaddition of beta-keto esters and 2 equiv of terminal acetylenes with dehydration. In the case of a 1,3-diketone, the corresponding acetophenone derivative and its deacylated compound can be synthesized selectively.
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
Mitsumi
M
Nishi
Salprima
S
Yudha S
Kazuhiko
K
Takai
D000480:Alkynes / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D008345:Manganese / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000480:Alkynes; D001555:Benzene Derivatives; D007659:Ketones; D008345:Manganese