Nucleophilic Amination of Aryl Halides with an Azanide Surrogate.

Autor: Cooper BD; Department of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK., Harris TD; Department of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK., Lim ERX; Department of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK., Hooper KA; Department of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK., Whitehead GFS; Department of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK., Carney JR; Chemical Development, Pharmaceutical Technology & Development, Operations, AstraZeneca, Macclesfield, SK10 2NA, UK., James MJ; Department of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Nov 25, pp. e202403952. Date of Electronic Publication: 2024 Nov 25.
DOI: 10.1002/chem.202403952
Abstrakt: We report the development of an azanide ( - NH 2 ) surrogate which enables the facile conversion of electron-deficient (hetero)aryl halides into primary N-aryl amines under transition-metal-free conditions. The designed amidine reagent is easy to prepare, bench stable, and undergoes facile N-arylation under basic conditions at 40 °C. Intermediate N-aryl amidines are readily cleaved to form N-aryl amines in situ through hydrolysis or base-promoted elimination. The developed surrogate is a safer and more selective alternative to existing anionic N-nucleophiles, such as alkali metal amides or azide salts.
(© 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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