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- Title
Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines.
- Authors
Hess, A.; Guelen, H. C.; Alandini, N.; Mourati, A.; Guersoy, Y. C.; Knochel, P.
- Abstract
A selective ortho,ortho'‐functionalization of readily available aryl oxazolines by two successive magnesiations with sBu2Mg 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 °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.
- Subjects
NITRILES; OXALYL chloride; ARYL iodides; ARYL bromides; CYANIDES; ARYL chlorides
- Publication
Chemistry - A European Journal, 2022, Vol 28, Issue 1, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202103700