Suzuki–Miyaura Cross-Coupling of 1,8-Diaminonaphthalene (dan)-Protected Arylboronic Acids

Abstract

We report a Suzuki–Miyaura cross-coupling reaction of 1,8-diaminonaphthalene (dan)-protected arylboronic acids in the presence of KOt-Bu, which does not require the removal of the dan moiety. Notably, the use of aryl-B(dan) in the Suzuki–Miyaura reaction provides a complementary solution to the protodeboronation problems. The base KOt-Bu plays a crucial role for the promotion of these cross-coupling reactions as it enables the formation of a borate salt. This reaction protocol was extended to the one-pot sequential Suzuki–Miyaura cross-coupling reaction of 4-[(pin)B]C6H4–B(dan), wherein the “less reactive” aryl-B(dan) moiety was cross-coupled preferentially.