Catalyst-free dehydrocoupling of amines, alcohols, and thiols with pinacol borane and 9-borabicyclononane (9-BBN)

Contrary to recent reports, the dehydrocoupling of pinacol borane and 9-borabicyclononane with a variety of amines, alcohols and thiols can be achieved under mild conditions without catalyst. This process involves the formation of Lewis acid-base adducts featuring a hydridic B-H in close proximity to an acidic Nu-H.