A molecular shuttle for hydrogen cyanide

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Science  19 Feb 2016:
Vol. 351, Issue 6275, pp. 817
DOI: 10.1126/science.aaf2215

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In recent decades, transition-metal catalysis has become an indispensable tool in organic synthesis. Nevertheless, there remains a need for practical, safe, and efficient protocols for some transformations. A challenging example is nickelcatalyzed hydrocyanation (1), in which nonactivated olefins (alkenes) are converted to branched or linear nitriles through addition of hydrogen cyanide (HCN) (see the figure, panel A). This transformation is used industrially on a very large scale to produce adiponitrile, a key intermediate for Nylon-66 (see the figure, panel B). However, it is rarely used in laboratory or fine chemical syntheses because of safety concerns regarding HCN, an extremely toxic, volatile, and flammable agent. On page 832 of this issue, Fang et al. (2) report a method that avoids the use of HCN in the conversion of alkenes to nitriles and vice versa.