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Electrochemically Initiated Oxidative Amination of Benzoxazoles Using Tetraalkylammonium Halides As Redox Catalysts

2014; American Chemical Society; Volume: 79; Issue: 20 Linguagem: Inglês

10.1021/jo501736w

1520-6904

Weijing Gao, Wei‐Cui Li, Cheng‐Chu Zeng, Hongyu Tian, Liming Hu, R. Daniel Little,

Sulfur-Based Synthesis Techniques

An electrochemically promoted coupling of benzoxazoles and amines has been developed, leading directly to the formation of 2-aminobenzoxazoles. The chemistry utilizes catalytic quantities of a tetraalkylammonium halide redox catalyst and is carried out under constant current conditions in a simple undivided cell. The use of excess chemical oxidant or large amounts of supporting electrolyte is avoided. This greatly simplifies the workup and isolation process and leads to a reduction in waste.