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

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

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.

Original language	English
Pages (from-to)	3049-3052
Number of pages	4
Journal	Chemical Communications
Volume	51
Issue number	15
DOIs	https://doi.org/10.1039/c4cc08434a
Publication status	Published - 21 Feb 2015
Externally published	Yes

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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

M3 - Article

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SN - 1359-7345

VL - 51

SP - 3049

EP - 3052

JO - Chemical Communications

JF - Chemical Communications

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ER -

Unprecedented directed lateral lithiations of tertiary carbons on NHC platforms

Abstract

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