B(C6F5)3-catalyzed one-pot selenation of phosphonates and indoles

Abstract

B(C₆F₅)₃-catalyzed one-pot formations of Se–P and C–Se bonds are described. A variety of selenocyanates coupled with phosphonates or indoles to provide the corresponding phosphoroselenoates and 3-selenylindoles in moderate to good yields. The distinct advantages of this one-pot protocol include the use of readily available starting materials, mild reaction conditions, and a broad substrate scope. Mechanistic studies suggest that the borane catalyst activates selenocyanates to form electrophilic species, which drive this selenation reaction.