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Azidative Aromatization of Quinone Methides Under Transition Metal and Solvent Free Conditions
Author(s) -
Xiu Haiping,
Li Tingting,
Song Chun,
Ma Yudao
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000900
Subject(s) - chemistry , aromatization , transition metal , catalysis , azide , hydrazoic acid , organic chemistry , solvent , combinatorial chemistry
Organic azides are synthetically and commercially useful intermediates with a wide variety of applications. In this work, azidative aromatization of quinone methides under transition metal and acid‐free conditions can avoid the forming of highly toxic and explosive hydrazoic acid and azide salts. The use of cesium carbonate as a catalyst and water as an effective additive, elimination of a transition metal catalyst, reaction solvent, and column chromatography separation led to an overall greener approach to access valuable benzyl azides in quantitative yields. Because the procedure can be used to prepare a serious of benzyl azides without contamination by any harmful transition metal residues, this new method has great potential in pharmaceutical synthesis and chemical biology studies.