Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 28, Issue 1, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202103700
Keywords
aryl nitriles; aryl oxazolines; cyanation; directed metalation; Grignard reagents
Categories
Funding
- Deutsche Forschungsgemeinschaft
- Ludwig-Maximilians-Universitat Munchen
- Projekt DEAL
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This study presents a novel method for the selective ortho, ortho'-functionalization of readily available aryl oxazolines using sBu(2)Mg in toluene followed by trapping reactions with electrophiles. The conversions of these nitriles to valuable heterocycles are reported, and a tentative mechanism is proposed for the reactions.
A selective ortho,ortho'-functionalization of readily available aryl oxazolines by two successive magnesiations with sBu(2)Mg in toluene followed by trapping reactions with electrophiles, such as (hetero)aryl iodides or bromides, iodine, tosyl cyanide, ethyl cyanoformate or allylic bromides (39 examples, 62-99 % yield) is reported. Treatment of these aryl oxazolines with excess oxalyl chloride and catalytic amounts of DMF (50 degrees C, 4 h) provided the corresponding nitriles (36 examples, 73-99 % yield). Conversions of these nitriles to valuable heterocycles are reported, and a tentative mechanism is proposed.
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