Intermolecular 'oxidative' aromatic substitution reactions of the imidazol-5-yl radical mediated by the 'reductant' Bu 3SnH

Padraig T.F. McLoughlin; Mairéad A. Clyne; Fawaz Aldabbagh

doi:10.1016/j.tet.2004.06.120

Intermolecular 'oxidative' aromatic substitution reactions of the imidazol-5-yl radical mediated by the 'reductant' Bu ₃SnH

Padraig T.F. McLoughlin
, Mairéad A. Clyne
, Fawaz Aldabbagh

National University of Ireland

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

Abstract

The reactivity of the imidazol-5-yl in comparison to the imidazol-2-yl and phenyl radical under the reductive conditions of Bu ₃SnH, in intermolecular substitution reactions onto various aromatic substrates is reported. The directing effect of the hetero atom or methyl substituent in aromatic substrates was found to be more important than the polarity of the attacking σ-radical in determining the major product isomer. Graphical Abstract

Original language	English
Pages (from-to)	8065-8071
Number of pages	7
Journal	Tetrahedron
Volume	60
Issue number	37
Early online date	22 Jul 2004
DOIs	https://doi.org/10.1016/j.tet.2004.06.120
Publication status	Published - 6 Sept 2004
Externally published	Yes

Keywords

Free radicals
Heterocycles
Imidazoles
Tributyltin hydride

Access to Document

10.1016/j.tet.2004.06.120Licence: Other

Cite this

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title = "Intermolecular 'oxidative' aromatic substitution reactions of the imidazol-5-yl radical mediated by the 'reductant' Bu 3SnH",

abstract = "The reactivity of the imidazol-5-yl in comparison to the imidazol-2-yl and phenyl radical under the reductive conditions of Bu 3SnH, in intermolecular substitution reactions onto various aromatic substrates is reported. The directing effect of the hetero atom or methyl substituent in aromatic substrates was found to be more important than the polarity of the attacking σ-radical in determining the major product isomer. Graphical Abstract",

keywords = "Free radicals, Heterocycles, Imidazoles, Tributyltin hydride",

author = "McLoughlin, \{Padraig T.F.\} and Clyne, \{Mair{\'e}ad A.\} and Fawaz Aldabbagh",

year = "2004",

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T1 - Intermolecular 'oxidative' aromatic substitution reactions of the imidazol-5-yl radical mediated by the 'reductant' Bu 3SnH

AU - McLoughlin, Padraig T.F.

AU - Clyne, Mairéad A.

AU - Aldabbagh, Fawaz

PY - 2004/9/6

Y1 - 2004/9/6

N2 - The reactivity of the imidazol-5-yl in comparison to the imidazol-2-yl and phenyl radical under the reductive conditions of Bu 3SnH, in intermolecular substitution reactions onto various aromatic substrates is reported. The directing effect of the hetero atom or methyl substituent in aromatic substrates was found to be more important than the polarity of the attacking σ-radical in determining the major product isomer. Graphical Abstract

AB - The reactivity of the imidazol-5-yl in comparison to the imidazol-2-yl and phenyl radical under the reductive conditions of Bu 3SnH, in intermolecular substitution reactions onto various aromatic substrates is reported. The directing effect of the hetero atom or methyl substituent in aromatic substrates was found to be more important than the polarity of the attacking σ-radical in determining the major product isomer. Graphical Abstract

KW - Free radicals

KW - Heterocycles

KW - Imidazoles

KW - Tributyltin hydride

U2 - 10.1016/j.tet.2004.06.120

DO - 10.1016/j.tet.2004.06.120

M3 - Article

AN - SCOPUS:4143067084

SN - 0040-4020

VL - 60

SP - 8065

EP - 8071

JO - Tetrahedron

JF - Tetrahedron

IS - 37