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.
This review describes recent advances in the synthesis of anthranilamide/1,8‐diaminonaphthalene‐substituted organoboron compounds with diminished boron Lewis acidity via catalytic B(aam)‐ and B(dan)‐installing borylation reactions, which have attracted growing attention especially in the last five years owing to their unique reactivity, regioselectivity, and the outstanding stability toward air and moisture of organoboron compounds obtained therefrom. Direct Suzuki–Miyaura cross‐couplings with R–B(aam)/B(dan), which were believed to be wholly unreactive until recently, are also discussed.
Copper-catalyzed reaction of organic halides with an unsymmetrical diboron, (pin)B–B(dan), which leads to the direct formation of masked organoboron compounds, is reported.
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