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Updated: May 10, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Metal-mediated coupling of a coordinated isocyanide and indazoles
Mikhail A Kinzhalov1, Vadim P Boyarskiy, Konstantin V Luzyanin
1Department of Chemistry, Saint Petersburg State University, Petrodvorec, Universitetskiy pr. 26, 198504 Saint Petersburg, Russian Federation.
Abstract:
A reaction between equimolar amounts of cis-[PdCl2(CNCy)2] (1) and indazole (HInd, 2) or 5-methylindazole (HInd(Me), 3) proceeded in refluxing CHCl3 for ca. 6 h affording the aminocarbene species cis-[PdCl2{C(Ind)=N(H)Cy}(CNCy)] (4) or cis-[PdCl2{C(Ind(Me))=N(H)Cy}(CNCy)] (5) in good (72-83%) isolated yields. Complexes 4 and 5 were characterized by elemental analyses (C, H, N), HR ESI(+)-MS, IR, and 1D ((1)H, (13)C{(1)H}) and 2D ((1)H,(1)H-COSY, (1)H,(13)C-HMQC/(1)H,(13)C-HSQC, (1)H,(13)C-HMBC) NMR spectroscopies, and complex 4 as well by X-ray diffraction. The observed coupling represents the first example of metal-mediated integration between any isocyanide and any aromatic heterocyclic system having an HN center.
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