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Development of a Telescoped Process for Preparation of N,O-Chelated Diarylborinates

A telescoped process has been developed for practical preparation of N,O-chelated four-coordinate diarylborinates via direct reaction of N,O-chelate ligands with a diarylborinate solution prepared by removal of magnesium via precipitation from a one-pot reaction of aryl bromides, magnesium, and tributylborate. Ten N,O-chelated diarylborinates of representative N,O-chelate ligands of 2-picolinic acid, quinolin-8-ol, N-dimethylglycine, and amino alcohols were readily obtained in good yields. The telescoped process not only minimizes chemical waste and circumvents tedious purification of diarylborinic acids but also eliminates handling of Grignard reagents and improves compatibility with acid-sensitive groups.