Issue 29, 2013
From the journal:

Dalton Transactions

Metal-mediated coupling of a coordinated isocyanide and indazoles†

Mikhail A. Kinzhalov,a   Vadim P. Boyarskiy,*a   Konstantin V. Luzyanin,ab   Fedor M. Dolgushinc  and  Vadim Yu. Kukushkinad  

* Corresponding authors

a Department of Chemistry, Saint Petersburg State University, Petrodvorec, Universitetskiy pr. 26, 198504 Saint Petersburg, Russian Federation
E-mail: vadim.boyarskiy@chem.spbu.ru

b Department of Chemistry, University of Liverpool, Crown Street, Liverpool L69 7ZD, United Kingdom

c A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Street 28, 119991 Moscow, Russian Federation

d Institute of Macromolecular Compounds of Russian Academy of Sciences, Bolshoii Pr. 31, 199004 Saint Petersburg, Russian Federation

Abstract

A reaction between equimolar amounts of cis-[PdCl2(CNCy)2] (1) and indazole (HInd, 2) or 5-methylindazole (HIndMe, 3) proceeded in refluxing CHCl3 for ca. 6 h affording the aminocarbene species cis-[PdCl2{C(Ind)[double bond, length as m-dash]N(H)Cy}(CNCy)] (4) or cis-[PdCl2{C(IndMe)[double bond, length as m-dash]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 (1H, 13C{1H}) and 2D (1H,1H-COSY, 1H,13C-HMQC/1H,13C-HSQC, 1H,13C-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.

Graphical abstract: Metal-mediated coupling of a coordinated isocyanide and indazoles

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Article information

DOI
https://doi.org/10.1039/C3DT51335A
Article type
Communication
Submitted
22 May 2013
Accepted
09 Jun 2013
First published
11 Jun 2013

Dalton Trans., 2013,42, 10394-10397

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Metal-mediated coupling of a coordinated isocyanide and indazoles

M. A. Kinzhalov, V. P. Boyarskiy, K. V. Luzyanin, F. M. Dolgushin and V. Yu. Kukushkin, Dalton Trans., 2013, 42, 10394 DOI: 10.1039/C3DT51335A

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