Direct Suzuki–Miyaura Coupling with Naphthalene-1,8-diaminato (dan)-Substituted Organoborons

Abstract

The actually direct Suzuki–Miyaura coupling with “protected” R–B(dan) (dan = naphthalene-1,8-diaminato) was demonstrated to smoothly occur without in situ deprotection of the B(dan) moiety. The use of t-BuOK (Ba(OH)2 in some cases) as a base under anhydrous conditions is the key to the successful cross-coupling, where R–B(dan) is readily converted into a transmetalation-active borate-form, regardless of the well-accepted diminished boron-Lewis acidity.