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Radical Amination with Sulfonyl Azides: A Powerful Method for the Formation of CN Bonds
Author(s) -
Panchaud Philippe,
Chabaud Laurent,
Landais Yannick,
Ollivier Cyril,
Renaud Philippe,
Zigmantas Sarunas
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200400027
Subject(s) - sulfonyl , chemistry , radical , amination , azide , electrophilic amination , moiety , alkyl , nucleophile , electrophile , combinatorial chemistry , organic chemistry , catalysis
Abstract A novel reaction for the introduction of an azide moiety by means of a mild radical process is currently under development. Sulfonyl azides are suitable azidating agents for nucleophilic radicals, such as secondary and tertiary alkyl radicals. More electrophilic radicals, such as enolate radicals, do not react with sulfonyl azides. This feature allowed the development of efficient intra‐ and intermolecular carboazidations of olefins. Due to the versatility of the azido group, this reaction has an important synthetic potential, as already demonstrated by the preparation of the core of several alkaloids, particularly those containing an amino‐substituted quaternary carbon center, such as FR901483.