36887-92-0Relevant articles and documents
NEW C-N-C BOND FORMATION REACTION USING NITROGENATION-TRANSMETALLATION PROCESS. NOVEL RING CONSTRUCTION OF INDOLE AND QUINOLINE DERIVATIVES.
Mori, Miwako,Uozumi, Yasuhiro,Shibasaki, Masakatsu
, p. 819 - 830 (1992)
Ketones and aryl or vinyl halides couple to give divinyl- or arylvinylamines in the presence of the titaniumisocyanate complex (1) and a palladium catalyst, via transmetallation of the titano imine complex (3) with aryl- or vinylpalladium bromide.
Nitrogen fixation: Synthesis of heterocycles using molecular nitrogen as a nitrogen source
Mori, Miwako,Akashi, Masaya,Hori, Masanori,Hori, Katsutoshi,Nishida, Mayumi,Sato, Yoshihiro
, p. 1655 - 1670 (2007/10/03)
Nitrogen fixation using transition metals is a fascinating process. We have already reported on the incorporation of molecular nitrogen into organic compounds using a titanium-nitrogen complex reported by Yamamoto. We developed a novel titanium-catalyzed nitrogenation procedure using TiCl4 in the presence of an excess amount of Li and TMSCl. In this reaction, a 1 atm pressure of nitrogen gas can be used and the reaction proceeds at room temperature. The procedure is very simple. A THF solution of TiCl4 or Ti(O iPr)4 (1 equiv.), Li (10 equiv.), and TMSCl (10 equiv.) was stirred under an atmosphere of nitrogen at room temperature overnight to give titanium-nitrogen complexes. Although the structures of the titanium-nitrogen complexes have not yet been determined, they would consist of N(TMS)3, X2TiN(TMS)2, and XTi=NTMS. Using this procedure, various heterocycles, such as indole, quinoline, pyrrole, pyrrolizine, and indolizine derivatives, could be synthesized from molecular nitrogen in good-to-moderate yields as a stoichiometric reaction based on a titanium complex by a one-pot reaction. Furthermore, monomorine I and pumiliotoxin C were synthesized from molecular nitrogen as a nitrogen source. This procedure was further extended for the syntheses of heterocycles using a catalytic amount of titanium complex; also, indole and pyrrole derivatives were obtained in high yields.
New C-N-C Bond Formation Reaction using the Nitrogenation-transmetallation Process
Uozumi, Yasuhiro,Mori, Miwako,Shibasaki, Masakatau
, p. 81 - 83 (2007/10/02)
Ketones and aryl or vinyl halides couple to give divinyl or arylvinyl amines in the presence of the titanium isocyanate complex 1 and a palladium catalyst, via transmetallation of the titano imine complex 6 with aryl or vinyl palladium bromide (THF tetrahydrofuran).
