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Issue 14, 2018
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Sonogashira reactions of alkyl halides catalyzed by NHC [CNN] pincer nickel(II) complexes

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Abstract

C(carbene)N(amido)N(amine)-pincer nickel(II) complexes [iPrCNN-Ni-Br] (6), [nBuCNN-Ni-Br] (7) and [BnCNN-Ni-Cl] (8) were synthesized. The catalytic performance of complexes 6–8 for Sonogashira cross-coupling reactions was explored. In a combination of 5 mol% catalyst loading of 6 and CuI/Cs2CO3/NaI/DMSO at different temperatures for the coupling reactions between alkyl iodides, bromides, chlorides and terminal alkynes, the corresponding coupling products were obtained in moderate to excellent yields. The mechanism of these catalytic reactions was discussed and partially supported by experiments. The phenylethynyl CNN pincer nickel complex 9 as a catalytically active complex was isolated and structurally characterized using X-ray diffraction.

Graphical abstract: Sonogashira reactions of alkyl halides catalyzed by NHC [CNN] pincer nickel(ii) complexes

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Publication details

The article was received on 02 May 2018, accepted on 23 May 2018 and first published on 28 May 2018


Article type: Paper
DOI: 10.1039/C8NJ02138D
Citation: New J. Chem., 2018,42, 11465-11470
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    Sonogashira reactions of alkyl halides catalyzed by NHC [CNN] pincer nickel(II) complexes

    Z. Wang, T. Zheng, H. Sun, X. Li, O. Fuhr and D. Fenske, New J. Chem., 2018, 42, 11465
    DOI: 10.1039/C8NJ02138D

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