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

doi:10.1002/anie.200503202

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

Pure And Applied Chemistry

Research output: Contribution to journal › Article

68 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.

Original language	English
Pages (from-to)	2370-2374
Number of pages	5
Journal	Angewandte Chemie
Volume	45
Issue number	15
DOIs	https://doi.org/10.1002/anie.200503202
Publication status	Published - 2006

Keywords

alkali metals
amides
complex-induced proximity effect
metalation
zinc
lithiation

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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",

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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

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 15

ER -