Nickel-catalyzed direct selenation of benzamides bearing an 8-quinolyl auxiliary with elemental selenium provides benzoisoselenazolones in good yield via carbon-selenium and nitrogen-selenium bond formation under aerobic conditions. In addition to aryl C-H bonds, the method can also be applied to alkenyl C-H bonds, constructing an isoselenazolone skeleton. Simple mechanistic analysis shows that the reaction proceeds through a rate-determining C-H bond cleavage. The obtained benzoisoselenazolones are transformed into various organoselenium compounds and utilized as the catalyst for bromolactonization of alkenoic acids.
An abundant and low toxicity iron catalyst has enabled regioselective annulation of alkenes with α-halocarboxylic acids and their derivatives. The reaction proceeds smoothly without any additional ligands, bases, and additives to afford a variety of γ-lactones in good yields. A proposed reaction pathway through radical annulation is supported by some mechanistic studies, involving radical clock and isotope labeling experiments. The present method was applied to the practical iron-powder-promoted synthesis of γ-lactones.
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