Pre-metalation structural insights into the use of alkali-metal-mediated zincation for directed ortho-metalation of a tertiary aromatic amide

W Clegg, S H Dale, E Hevia, G W Honeyman, R E Mulvey

Research output: Contribution to journalArticle

67 Citations (Scopus)

Abstract

The predator meets its prey in the structure of [{(iPr)2NC(Ph)(O)}Li(μ-tmp)(μ-tBu)Zn(tBu)] which reveals an aromatic amide–alkali metal zincate “precomplex” for directed ortho-metalation (DoM) that exists prior to the devouring (ortho-zincation) of the amide by the zincate. tmp=2,2,6,6-tetramethylpiperidide.
LanguageEnglish
Pages2370-2374
Number of pages5
JournalAngewandte Chemie
Volume45
Issue number15
DOIs
Publication statusPublished - 2006

Fingerprint

Alkali Metals
Amides
2,2,6,6-tetramethylpiperidide

Keywords

  • alkali metals
  • amides
  • complex-induced proximity effect
  • metalation
  • zinc
  • lithiation

Cite this

@article{47bfd690882147bfa26db973e5767662,
title = "Pre-metalation structural insights into the use of alkali-metal-mediated zincation for directed ortho-metalation of a tertiary aromatic amide",
abstract = "The predator meets its prey in the structure of [{(iPr)2NC(Ph)(O)}Li(μ-tmp)(μ-tBu)Zn(tBu)] which reveals an aromatic amide–alkali metal zincate “precomplex” for directed ortho-metalation (DoM) that exists prior to the devouring (ortho-zincation) of the amide by the zincate. tmp=2,2,6,6-tetramethylpiperidide.",
keywords = "alkali metals, amides, complex-induced proximity effect, metalation, zinc, lithiation",
author = "W Clegg and Dale, {S H} and E Hevia and Honeyman, {G W} and Mulvey, {R E}",
year = "2006",
doi = "10.1002/anie.200503202",
language = "English",
volume = "45",
pages = "2370--2374",
journal = "Angewandte Chemie International Edition",
issn = "1433-7851",
number = "15",

}

Pre-metalation structural insights into the use of alkali-metal-mediated zincation for directed ortho-metalation of a tertiary aromatic amide. / Clegg, W ; Dale, S H ; Hevia, E ; Honeyman, G W ; Mulvey, R E .

In: Angewandte Chemie, Vol. 45, No. 15, 2006, p. 2370-2374.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Pre-metalation structural insights into the use of alkali-metal-mediated zincation for directed ortho-metalation of a tertiary aromatic amide

AU - Clegg, W

AU - Dale, S H

AU - Hevia, E

AU - Honeyman, G W

AU - Mulvey, R E

PY - 2006

Y1 - 2006

N2 - The predator meets its prey in the structure of [{(iPr)2NC(Ph)(O)}Li(μ-tmp)(μ-tBu)Zn(tBu)] which reveals an aromatic amide–alkali metal zincate “precomplex” for directed ortho-metalation (DoM) that exists prior to the devouring (ortho-zincation) of the amide by the zincate. tmp=2,2,6,6-tetramethylpiperidide.

AB - The predator meets its prey in the structure of [{(iPr)2NC(Ph)(O)}Li(μ-tmp)(μ-tBu)Zn(tBu)] which reveals an aromatic amide–alkali metal zincate “precomplex” for directed ortho-metalation (DoM) that exists prior to the devouring (ortho-zincation) of the amide by the zincate. tmp=2,2,6,6-tetramethylpiperidide.

KW - alkali metals

KW - amides

KW - complex-induced proximity effect

KW - metalation

KW - zinc

KW - lithiation

U2 - 10.1002/anie.200503202

DO - 10.1002/anie.200503202

M3 - Article

VL - 45

SP - 2370

EP - 2374

JO - Angewandte Chemie International Edition

T2 - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 15

ER -