Olefin shuffle for just a nickel: Controlling the geometry of carbon-carbon double bonds is a central component of chemical manufacturing. One useful trick is to shift hydrogen atoms around to interconvert C=C isomers selectively. However, this approach typically requires precious metals. Kapat et al. now report that more-abundant nickel can catalyze rapid conversion of terminal olefins into internal olefins with high selectivity for trans geometry. The odd-electron nickel complex relies on a radical mechanism to shuttle hydrogen to the terminal carbon from the saturated carbon adjacent to the double bond. Science , this issue p. 391

Recent advances in radical azidation using sulfonyl azides are presented. For instance, radical carboazidation using α-iodoketones, desulfitative carboazidation, and anti-Markovnikov hydroazidation of alkenes are described. These novel methods tolerate a large number of functional groups and allow the synthesis of organic azides that would be difficult to synthesize otherwise. The transformation of the azides using reductive processes as well as a Schmidt reaction under nonacidic conditions were used to synthesize alkaloids including indolizidine 167B, monomorine I, cylindricine C, and lepadiformine C.