Cu(0), O2 and mechanical forces: a saving combination for efficient production of Cu–NHC complexes† †Electronic supplementary information (ESI) available: Operating procedures and characterization data. See DOI: 10.1039/c6sc03182j Click here for additional data file.

نویسندگان

  • Audrey Beillard
  • Thomas-Xavier Métro
  • Xavier Bantreil
  • Jean Martinez
  • Frédéric Lamaty
چکیده

Mechanical forces induced by ball-milling agitation enabled the highly efficient and widely applicable synthesis of Cu–carbene complexes from N,N-diaryl-imidazolium salts and metallic copper. The required amount of gaseous dioxygen and insoluble copper could be reduced down to stoichiometric quantities, while reaction rates clearly outperformed those obtained in solution. Utilisation of Cu(0) as the copper source enabled the application of this approach to a wide array of N,N-diaryl-imidazolium salts (Cl , BF4 and PF6 ) that transferred their counter anion directly to the organometallic complexes. Cu–NHC complexes could be produced in excellent yields, including utilisation of highly challenging substrates. In addition, five unprecedented organometallic complexes are reported.

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منابع مشابه

Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction† †Electronic supplementary information (ESI) available: Experimental procedures and characterization date (NMR, IR, MS, HPLC). CCDC 1437686. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5cc09581f Click here for additional data file. Click here for additional data file.

An NHC-catalyzed Michael/Michael/esterification domino reaction via homoenolate/enolate intermediates for the asymmetric synthesis of tetrasubstituted cyclopentanes bearing four contiguous stereocenters is described. A variety of α,β-unsaturated aldehydes and 2-nitroallylic acetates react well with good domino yields and high stereoselectivities.

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عنوان ژورنال:

دوره 8  شماره 

صفحات  -

تاریخ انتشار 2017