Unprecedented directed lateral lithiations of tertiary carbons on NHC platforms-Reference-Cited by-同舟云学术

Unprecedented directed lateral lithiations of tertiary carbons on NHC platforms

Published:2015 Issue:15 Volume:51 Page:3049-3052
ISSN:1359-7345
Container-title:Chemical Communications
language:en
Short-container-title:Chem. Commun.

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

Link

http://pubs.rsc.org/en/content/articlepdf/2015/CC/C4CC08434A

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3. Directed Remote Aromatic Metalations: Mechanisms and Driving Forces

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5. Role of Organolithium Aggregates and Mixed Aggregates in Organolithium Mechanisms

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