Catalytic reversible alkene-nitrile interconversion through controllable transfer hydrocyanation

Author:

Fang Xianjie1,Yu Peng1,Morandi Bill1

Affiliation:

1. Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Nordrhein-Westfalen 45470, Germany.

Abstract

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

Funder

Max-Planck-Society

Max-Planck-Institut fur Kohlenforschung

Publisher

American Association for the Advancement of Science (AAAS)

Subject

Multidisciplinary

Reference65 articles.

1. P. Pollak G. Romeder F. Hagedorn H. Gelbke “Nitriles ” in Ullman’s Encyclopedia of Industrial Chemistry (Wiley-VCH Weinheim Germany ed. 5 1985) vol. A17 p. 363.

2. M. B. Smith J. March March’s Advanced Organic Chemistry: Reactions Mechanisms and Structure (Wiley-Interscience Hoboken NJ ed. 6 2007).

3. S. Patai J. Zabicky Eds. “The Alkenes: Volumes 1 and 2 ” in PATAI’s Chemistry of Functional Groups (Wiley 1964/1970).

4. R. H. Grubbs Handbook of Metathesis (Wiley-VCH Weinheim Germany 2003).

5. W. C. Drinkard Jr. US 3496218A 1970 .

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