Unprecedented directed lateral lithiations of tertiary carbons on NHC platforms

Author:

Danopoulos Andreas A.12345,Braunstein Pierre56734,Rezabal Elixabete89104,Frison Gilles89104

Affiliation:

1. Institute for Advanced Study (USIAS)

2. Université de Strasbourg (UdS)

3. 67081 Strasbourg Cedex

4. France

5. Laboratoire de Chimie de Coordination

6. Institut de Chimie (UMR 7177 CNRS)

7. UdS

8. Laboratoire de Chimie Moléculaire

9. Ecole Polytechnique and CNRS

10. 91128 Palaiseau Cedex

Abstract

Deprotonation of the tautomeric mixture of 4-amido-imidazoliums and 4-amino-N-heterocyclic carbenes led to dilithiated dianionic functional NHCs, via an unprecedented regioselective, directed remote lateral lithiation of a tertiary CHMe2 carbon. DFT calculations support that the nature of products is under thermodynamic control.

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

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