Insertion of polar and nonpolar unsaturated molecules into carbon-rhenium bonds generated by C-H bond activation: synthesis of phthalimidine and indene derivatives.
A rhenium complex, [ReBr(CO)(3)(thf)](2), catalyzes the reaction of an aromatic aldimine with an isocyanate and an acetylene to give a phthalimidine and an indene derivative in a quantitative yield, respectively. The reactions proceed via C-H bond activation, insertion of the isocyanate or the acetylene, intramolecular nucleophilic cyclization to the aldimine of the generated amido- or alkenyl-rhenium species, and reductive elimination. In contrast to ruthenium and rhodium catalysts, which are usually employed in this type of reaction, the rhenium catalyst promotes the insertion of a polar unsaturated molecule. This occurs more easily than the insertion of a nonpolar unsaturated molecule.
Kuninobu
Yoichiro
Y
Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Okayama 700-8530, Japan. kuninobu@cc.okayama-u.ac.jp
Tokunaga
Yukimi
Y
Kawata
Atsushi
A
Takai
Kazuhiko
K