Unprecedented directed lateral lithiations of tertiary carbons on NHC platforms

Andreas A. Danopoulos; Pierre Braunstein; Elixabete Rezabal; Gilles Frison

doi:10.1039/c4cc08434a

Unprecedented directed lateral lithiations of tertiary carbons on NHC platforms

Andreas A. Danopoulos
, Pierre Braunstein
, Elixabete Rezabal
, Gilles Frison

Institute for Advanced Study (USIAS)
Université de Strasbourg
Laboratoire de Chimie de Coordination
Institut de Chimie de Strasbourg
CNRS

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

23 Citations (Scopus)

Résumé

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.

langue originale	Anglais
Pages (de - à)	3049-3052
Nombre de pages	4
journal	Chemical Communications
Volume	51
Numéro de publication	15
Les DOIs	https://doi.org/10.1039/c4cc08434a
état	Publié - 21 févr. 2015
Modification externe	Oui

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10.1039/c4cc08434a

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title = "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.",

author = "Danopoulos, \{Andreas A.\} and Pierre Braunstein and Elixabete Rezabal and Gilles Frison",

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AU - Danopoulos, Andreas A.

AU - Braunstein, Pierre

AU - Rezabal, Elixabete

AU - Frison, Gilles

PY - 2015/2/21

Y1 - 2015/2/21

N2 - 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.

AB - 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.

U2 - 10.1039/c4cc08434a

DO - 10.1039/c4cc08434a

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VL - 51

SP - 3049

EP - 3052

JO - Chemical Communications

JF - Chemical Communications

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Unprecedented directed lateral lithiations of tertiary carbons on NHC platforms

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