Cupric imide

Reaction of 3,5-di-f-butyl-l,2-benzoquinone with pyridine cupric methoxychloride and anhydrous ammonia in pyridine gives the imide 159 (-50%) (81JA5795). The lactone dimer 160 is formed in 51% )deld from 3,6-di-f-butyl-l,2-benzoquinone and 3,3-dimethylbut-l-ynyl-lithium (99MI350). 

Arylation of a wide range of NH/OH/SH substrates by oxidative cross-coupling with boronic acids in the presence of catalytic cupric acetate and either triethyl-amine or pyridine at room temperature in air. The reaction works for amides, amines, anilines, azides, hydantoins, hydrazines, imides, imines, nitroso, pyrazi-nones, pyridones, purines, pyrimidines, sulfonamides, sulfinates, sulfoximines, ureas, alcohols, phenols, and thiols. It is also the mildest method for NIO-vinylation. The boronic acids can be replaced with siloxanes or starmanes. The mild condition of this reaction is an advantage over Buchwald-Hartwig s Pd-catalyzed cross-coupling. The Chan-Lam C-X bond cross-coupling reaction is complementary to Suzuki-Miyaura s C-C bond cross-coupling reaction. 

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