Rhenium- and manganese-catalyzed carbon–carbon bond formation using 1,3-dicarbonyl compounds and alkynes*

نویسندگان

  • Yoichiro Kuninobu
  • Atsushi Kawata
  • Salprima S. Yudha
  • Hisatsugu Takata
  • Mitsumi Nishi
  • Kazuhiko Takai
چکیده

Abstract: A rhenium complex, [ReBr(CO)3(thf)]2, catalyzed insertion of terminal alkynes into a C–H bond of active methylene sites of 1,3-dicarbonyl compounds. When a catalytic amount of isocyanide or molecular sieves was added to the reaction mixture, the reaction course changed markedly, and insertion of alkynes into a C–C single bond between αand β-positions of cyclic and acyclic β-keto esters occurred. The formed acyclic δ-keto esters could be converted to 2-pyranones, which were applied to the synthesis of multisubstituted aromatic compounds via the Diels–Alder reaction and successive elimination of carbon dioxide. In the case of the rhenium-catalyzed reactions between terminal alkynes and β-keto esters without substituent at the α-position, tetrasubstituted benzenes were produced regioselectively by two-to-one reaction of the components. The yields of tetrasubstituted benzenes were improved by using a manganese catalyst.

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تاریخ انتشار 2010