Alkynylboranes: A Practical Approach by Zinc-Catalyzed Dehydrogenative Coupling of Terminal Alkynes with 1,8-Naphthalenediaminatoborane

Under zinc Lewis acid catalysis, terminal alkynes coupled dehydrogenatively with 1,8-naphthalenediaminatoborane [HB(dan)]. It is important to note that the resulting alkynylboranes with an C(sp)-B(dan) bond are isolable by column chromatography on silica gel (SiO2) and are usable as coupling partners for palladium- and copper-catalyzed cross-coupling reactions with (hetero) aryl halides.