Nickel-Catalyzed Reductive Cross-Coupling of Allylammonium Salts with Alkyl Iodides.

An unprecedented reductive cross-coupling reaction of allylammonium salts with alkyl electrophiles has been established through C-N bond cleavage. A range of allylammonium bromides smoothly participated in the nickel-catalyzed zinc-mediated allyl-alkyl cross-electrophile coupling reaction with alkyl iodides, delivering structurally diverse alkene products in moderate to good yields with high linear selectivity. Preliminary mechanistic experiments are consistent with the formation of an alkyl radical from the alkyl iodide.

Copper-catalyzed C-3 benzylation of quinoxalin-2(1H)-ones with benzylsulfonyl hydrazides.

An unprecedented use of benzylsulfonyl hydrazides as benzylating agents has been demonstrated in the direct C-3 benzylation of quinoxalin-2(1H)-ones. A range of benzylsulfonyl hydrazides participated in the C-3 benzylation of quinoxalin-2(1H)-ones with CuCN as the catalyst and DTBP as the oxidant, delivering structurally diverse 3-benzylquinoxalin-2(1H)-ones in moderate to good yields.