Synergic synthesis of benzannulated zincabicyclic complexes, alpha-zincated n ylides, through sodium-TMEDA-mediated zincation of a haloarene

D.R. Armstrong; L. Balloch; William Clegg; S.H. Dale; P. Garcia-Alvarez; E. Hevia; L.M. Hogg; A.R. Kennedy; R.E. Mulvey; Charles O'Hara

doi:10.1002/anie.200904506

Synergic synthesis of benzannulated zincabicyclic complexes, alpha-zincated n ylides, through sodium-TMEDA-mediated zincation of a haloarene

D.R. Armstrong, L. Balloch, William Clegg, S.H. Dale, P. Garcia-Alvarez, E. Hevia, L.M. Hogg, A.R. Kennedy, R.E. Mulvey, Charles O'Hara

Pure And Applied Chemistry

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

18 Citations (Scopus)

Abstract

Double role for sodium: Within a synergic sodium TMP-zincate reagent, sodium mediates the direct ortho-zincation of chlorobenzene and delivers the TMEDA ligand to nucleophilically attack the benzene ring, thereby generating novel open and cyclic zinc zwitterions (example shown). TMP=2,2,6,6-tetramethylpiperidide; TMEDA=N,N,N,N-tetramethylethylenediamine.

Original language	English
Pages (from-to)	8675-8678
Number of pages	4
Journal	Angewandte Chemie
Volume	48
Issue number	46
DOIs	https://doi.org/10.1002/anie.200904506
Publication status	Published - 2 Nov 2009

Keywords

alkali metals
cooperative effects
metallacyclic compounds
metalation
zinc

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title = "Synergic synthesis of benzannulated zincabicyclic complexes, alpha-zincated n ylides, through sodium-TMEDA-mediated zincation of a haloarene",

abstract = "Double role for sodium: Within a synergic sodium TMP-zincate reagent, sodium mediates the direct ortho-zincation of chlorobenzene and delivers the TMEDA ligand to nucleophilically attack the benzene ring, thereby generating novel open and cyclic zinc zwitterions (example shown). TMP=2,2,6,6-tetramethylpiperidide; TMEDA=N,N,N,N-tetramethylethylenediamine.",

keywords = "alkali metals, cooperative effects, metallacyclic compounds, metalation, zinc",

author = "D.R. Armstrong and L. Balloch and William Clegg and S.H. Dale and P. Garcia-Alvarez and E. Hevia and L.M. Hogg and A.R. Kennedy and R.E. Mulvey and Charles O'Hara",

year = "2009",

month = nov,

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doi = "10.1002/anie.200904506",

language = "English",

volume = "48",

pages = "8675--8678",

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TY - JOUR

T1 - Synergic synthesis of benzannulated zincabicyclic complexes, alpha-zincated n ylides, through sodium-TMEDA-mediated zincation of a haloarene

AU - Armstrong, D.R.

AU - Balloch, L.

AU - Clegg, William

AU - Dale, S.H.

AU - Garcia-Alvarez, P.

AU - Hevia, E.

AU - Hogg, L.M.

AU - Kennedy, A.R.

AU - Mulvey, R.E.

AU - O'Hara, Charles

PY - 2009/11/2

Y1 - 2009/11/2

N2 - Double role for sodium: Within a synergic sodium TMP-zincate reagent, sodium mediates the direct ortho-zincation of chlorobenzene and delivers the TMEDA ligand to nucleophilically attack the benzene ring, thereby generating novel open and cyclic zinc zwitterions (example shown). TMP=2,2,6,6-tetramethylpiperidide; TMEDA=N,N,N,N-tetramethylethylenediamine.

AB - Double role for sodium: Within a synergic sodium TMP-zincate reagent, sodium mediates the direct ortho-zincation of chlorobenzene and delivers the TMEDA ligand to nucleophilically attack the benzene ring, thereby generating novel open and cyclic zinc zwitterions (example shown). TMP=2,2,6,6-tetramethylpiperidide; TMEDA=N,N,N,N-tetramethylethylenediamine.

KW - alkali metals

KW - cooperative effects

KW - metallacyclic compounds

KW - metalation

KW - zinc

U2 - 10.1002/anie.200904506

DO - 10.1002/anie.200904506

M3 - Article

SN - 0044-8249

VL - 48

SP - 8675

EP - 8678

JO - Angewandte Chemie

JF - Angewandte Chemie

IS - 46

ER -

Synergic synthesis of benzannulated zincabicyclic complexes, alpha-zincated n ylides, through sodium-TMEDA-mediated zincation of a haloarene

Abstract

Keywords

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