BF·OEt catalyzed 1,6-conjugate addition of tert-butyl isocyanide to para-quinone methides and fuchsones for the synthesis of α-diaryl and α-triaryl nitriles has been reported. This protocol allows α-diaryl- and α-triaryl nitriles to be accessed in good to excellent yields and with a broad substrate scope, which could be further functionalized to give a versatile set of products. This is the first example wherein tert-butyl isocyanide has been used as a cyanide source for the 1,6-conjugate addition.
An efficient regioselective functionalization of 2aryl-heteroarenes and aryl aldehydes via an azaaryl BF 2 complex has been developed. Mechanistically the reaction comprises fluoride to bromide ligand exchange on an aryl boron species and consecutive CÀ B bond cleavage to deliver a broad range of functionalized products. The reaction is high yielding, has a broad substrate scope where several different heteroarenes can be functionalized with chloro, bromo, iodo, hydroxyl, amine and BF 2 in a highly regioselective fashion. The method can be applied for late-stage functionalization or for rapid skeleton remodeling with for instance crosscouplings.
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