Liquid assisted grinding has been successfully applied to eliminate the requirements of chemical activators and anhydrous solvents in nickel-catalyzed, manganese-mediated cross-electrophile coupling between aryl and alkyl bromides. In addition to...

Aryltriazenes can hardly take part in productive organic transformations unless stoichiometric Brönsted or Lewis acid activators are used. We report here for the first time a palladiumcatalyzed Suzuki coupling of aryltriazenes activated by a sulfonyl group at N3 atom under the common basic conditions. Benefiting from elimination of stoichiometric acid activators, activated aryltriazenes could efficiently couple with arylboronic acids to afford diaryls in modest to excellent yields by using a simple catalyst at low loading, 0.3 mol% Pd(PPh 3 ) 2 Cl 2 . Scope and limitation of the coupling are demonstrated with 26 examples.

A highly efficient acylative cross-coupling of trialkylboranes with activated amides has been effected at room temperature to give the corresponding alkyl ketones in good to excellent yields by using 1,3-bis(2,6-diisopropyl)phenylimidazolylidene and 3-chloropyridine co-supported palladium chloride, the PEPPSI catalyst, in the presence of K2CO3 in methyl tert-butyl ether. The scope and limitations of the protocol were investigated, showing good tolerance of acyl, cyano, and ester functional groups in the amide counterpart while halo group competed via the classical Suzuki coupling. The trialkylboranes generated in situ by hydroboration of olefins with BH3 or 9-BBN performed similarly to those separately prepared, making this protocol more practical.

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