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Air-stable and highly efficient indenyl-derived phosphine ligand: Application to Buchwald–Hartwig amination reactions

2-Mesitylindenyl phosphine ligand (1) and [(2-mesitylindenyl)dicyclohexyl-phosphine]PdCl2 (2) have been synthesized and fully characterized by NMR and elemental analysis, as well as by X-ray crystallography for 2. A Highly active catalyst system derived from a palladium precatalyst and bulky 2-mesitylindenyl phosphine ligand (1) for the Buchwald–Hartwig amination reaction of aryl halides with primary and secondary amines has been developed. This method allows for the preparation of a wide variety of amines in moderate to excellent yields and displays a high level of activity for the coupling of aryl chlorides as well as hindered aryl bromides.
Graphical Abstract Highlights 2-Mesitylindenyl phosphine ligand and [(2-mesitylindenyl)dicyclohexyl phosphine]-PdCl2 have been synthesized, and utilized in the palladium-catalyzed Buchwald–Hartwig amination reaction, providing good to excellent yields of amination products.

  • ► 2-Mesitylindenyl phosphine ligand (1) has been synthesized. ► [(2-Mesitylindenyl)dicyclohexyl-phosphine]PdCl2 (2) has been synthesized. ► A highly active catalyst system for the C–N coupling reaction has been developed.

    Authors:   Xiaowei Hao, Jia Yuan, Guang-Ao Yu, Ming-Qiang Qiu, Neng-Fang She, Yue Sun, Cui Zhao, Shu-Lan Mao, Jun Yin, Sheng-Hua Liu
    Journal:   Journal of Organometallic Chemistry
    Year:   2012
    DOI:   10.1016/j.jorganchem.2012.02.007
    Publication date:   23-04-2012
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