Unprecedented directed lateral lithiations of tertiary carbons on NHC platforms

Abstract : Unexpected and unprecedented directed remote lateral lithiation at one CH(CH3)2 of the 3-(2,6-di-isopropylphenyl) wingtip took place upon the reaction of functionalised N-heterocyclic carbene-type molecules with excess of LiCH2SiMe3, leading to dilithiated dianionic 4-amido-N-heterocyclic carbenes. DFT calculations show that the nature of the isolated species are under thermodynamic control.
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Andreas A. Danopoulos, Pierre Braunstein, Elixabete Rezabal, Gilles Frison. Unprecedented directed lateral lithiations of tertiary carbons on NHC platforms. Chemical Communications, Royal Society of Chemistry, 2015, 51, pp.3049-3052. ⟨10.1039/C4CC08434A⟩. ⟨hal-01086025⟩

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