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Updated: May 6, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Base-promoted formal arylation of benzo[d]oxazoles with acyl chloride
Lei Wang1, Xinyi Ren, Jintao Yu
1School of Petrochemical Engineering, Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, Jiangsu Province Key Laboratory of Fine Petrochemical Engineering, Changzhou University , Changzhou 213164, P. R. China.
Abstract:
A base-promoted formal arylation of benzo[d]oxazoles with acyl chloride was achieved in moderate to good yields. This reaction was triggered by the N-acylation of oxazole to form an iminium intermediate. Then, the addition of H2O to the iminium formed the hemiacetal intermediate. After the sequential ring-opening, extrusion of CO, the ring closure, the dehydration delivered the formal arylation product. In comparison with the transition-metal-catalyzed methodology, it represents an alternative arylation method leading to 2-arylbenzooxazole.
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