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Catalytic reversible alkene-nitrile interconversion through controllable transfer hydrocyanation

Science  19 Feb 2016:
Vol. 351, Issue 6275, pp. 832-836
DOI: 10.1126/science.aae0427

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A route to nitrile that bypasses cyanide

The toxicity of hydrogen cyanide (HCN) is well known. Nonetheless, numerous useful nitrile compounds contain CN groups, and the reaction of HCN with C=C double bonds is often used. Fang et al. now report an alternative to shuttle a CN group from one molecule to another that relies on Ni and Al catalysts (see the Perspective by Schmalz). This transfer procedure circumvents the need for HCN and can be applied to complex substrates using a simple sacrificial nitrile donor. It can also be run “in reverse” to derive an olefin of interest from a nitrile precursor.

Science, this issue p. 832; see also p. 817

Abstract

Nitriles and alkenes are important synthetic intermediates with complementary reactivity that play a central role in the preparation of materials, pharmaceuticals, cosmetics, and agrochemicals. Here, we report a nickel-catalyzed transfer hydrocyanation reaction between a wide range (60 examples) of alkyl nitriles and alkenes. This strategy not only overcomes the toxicity challenge posed by the use of HCN in traditional approaches, but also encompasses distinct chemical advances, including retro-hydrocyanation and anti-Markovnikov regioselectivity. In a broader context, this work highlights an approach to the reversible hydrofunctionalization of alkenes through thermodynamically controlled transfer reactions to circumvent the use of volatile and hazardous reagents in the laboratory.

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