Tuning the basicity of synergic bimetallic reagents: switching the regioselectivity of the direct dimetalation of toluene from 2,5-to 3,5-positions

V.L. Blair, L.M. Carrella, W. Clegg, B. Conway, R.W. Harrington, L.M. Hogg, J. Klett, R.E. Mulvey, Eva Rentschler, Luca Russo

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

Meta-meta metalation: Remarkably, toluene can be directly dimanganated or dimagnesiated at the 3,5-positions using bimetallic bases with active Me3SiCH2 ligands (see scheme, blue). In contrast, n-butyl ligands lead to 2,5-metalation (red). tmp=2,2,6,6-tetramethylpiperidide.
LanguageEnglish
Pages6208-6211
Number of pages4
JournalAngewandte Chemie
Volume47
Issue number33
DOIs
Publication statusPublished - 4 Aug 2008

Fingerprint

Toluene
Ligands
2,2,6,6-tetramethylpiperidide

Keywords

  • alkali metals
  • inverse crown compounds
  • magnesium
  • manganese
  • metalation

Cite this

Blair, V.L. ; Carrella, L.M. ; Clegg, W. ; Conway, B. ; Harrington, R.W. ; Hogg, L.M. ; Klett, J. ; Mulvey, R.E. ; Rentschler, Eva ; Russo, Luca. / Tuning the basicity of synergic bimetallic reagents : switching the regioselectivity of the direct dimetalation of toluene from 2,5-to 3,5-positions. In: Angewandte Chemie. 2008 ; Vol. 47, No. 33. pp. 6208-6211.
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abstract = "Meta-meta metalation: Remarkably, toluene can be directly dimanganated or dimagnesiated at the 3,5-positions using bimetallic bases with active Me3SiCH2 ligands (see scheme, blue). In contrast, n-butyl ligands lead to 2,5-metalation (red). tmp=2,2,6,6-tetramethylpiperidide.",
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Blair, VL, Carrella, LM, Clegg, W, Conway, B, Harrington, RW, Hogg, LM, Klett, J, Mulvey, RE, Rentschler, E & Russo, L 2008, 'Tuning the basicity of synergic bimetallic reagents: switching the regioselectivity of the direct dimetalation of toluene from 2,5-to 3,5-positions' Angewandte Chemie, vol. 47, no. 33, pp. 6208-6211. https://doi.org/10.1002/anie.200801158

Tuning the basicity of synergic bimetallic reagents : switching the regioselectivity of the direct dimetalation of toluene from 2,5-to 3,5-positions. / Blair, V.L.; Carrella, L.M.; Clegg, W.; Conway, B.; Harrington, R.W.; Hogg, L.M.; Klett, J.; Mulvey, R.E.; Rentschler, Eva; Russo, Luca.

In: Angewandte Chemie, Vol. 47, No. 33, 04.08.2008, p. 6208-6211.

Research output: Contribution to journalArticle

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AU - Carrella, L.M.

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AU - Conway, B.

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AU - Hogg, L.M.

AU - Klett, J.

AU - Mulvey, R.E.

AU - Rentschler, Eva

AU - Russo, Luca

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KW - alkali metals

KW - inverse crown compounds

KW - magnesium

KW - manganese

KW - metalation

U2 - 10.1002/anie.200801158

DO - 10.1002/anie.200801158

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