1071935-58-4Relevant articles and documents
Coupling between 3-iminoisoindolin-1-ones and complexed isonitriles as a metal-mediated route to a novel type of palladium and platinum iminocarbene species
Luzyanin, Konstantin V.,Pombeiro, Armando J.L.,Haukka, Matti,Kukushkin, Vadim Yu.
, p. 5379 - 5389 (2008)
The reaction between isonitrile in cw-[MCl2(C=NR)2] [M = Pd, R = Cy 1, But 2, C6H3(2,6-Me 2) 3; M = Pt, R = Cy 4, But 5, C6H 3(2,6-Me2) 6] and various unsubstituted or substituted iminoisoindolin-1-ones HN=CC6R1R2R 3R4CONH [R1 - R4 = H 7; R 1, R3, R4 = H, R2 = Me/R 1, R2, R4 = H, R3 = Me 8 (isomeric mixture); R1, R4 = H, R2, R3 = Cl 9] proceeds under reflux conditions in CHCl3 for 2 h. The subsequent workup provides complexes [MC1{C(N=C(C6R1R 2R3R4CON))=N(H)R}(C≡NR)] (M = Pd, 10-18; M = Pt, 19-27), bearing a novel type of carbene ligands, which were isolated in good (80-85% for the PdII complexes) to moderate (60-65% for the PtII species) yields. The addition of the iminoisoindolin-1-one to isonitriles is metal-mediated and has a general character. The reaction of cis-[PtCl2(C=NC6H4OMe-4)2] (28) with 7 affords a mixture of PtII-containing species including the monoadduct [PtCl{C(N=C(C6H4CON))=N(H)C6H 4OMe-4}(C≡NC6H4OMe-4)] (29), the unusual binuclear compound [Pt2{C(N=C(C6H4CON))=N(H) C6H4OMe-4}2(C≡NC6H 4OMe-4)2(μ-HN=CC6H4-CON)](Cl) (30) with a bridging monodeprotonated 3-iminoisoindolin-1-one, and [Pt(C 6H4CONC= NH){C(N=C(C6H4CON))=N(H) C6H4OMe-4}(C≡NC6H4OMe-4)] (31), the latter resulting from the replacement of the chloro ligand in 29 by the deprotonated iminoisoindolin-1-one. Complexes 10-27 were characterized by elemental analyses (C, H, N), ESI+-MS, IR, and ID (1H, 13C{1H}) and 2D (1H,1H-COSY, 1H,13C-HMQC/1H,13C-HSQC, 1H,13C-HMBC) NMR spectroscopies, while 29-31 by ESI +-MS, IR, and 1H NMR. In addition, the structures of three carbene complexes (10, 27, and 30) were elucidated by single-crystal X-ray diffraction analysis.
