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Activation of reducing agents. Sodium hydride containing complex reducing agents 22. New coupling reaction with “nickel doped” complex reducing agent.

✍ Scribed by Régis Vanderesse; Yves Fort; Sandrine Becker; Paul Caubere

Publisher: Elsevier Science
Year: 1986
Tongue: French
Weight: 178 KB
Volume: 27
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)84838-8

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✦ Synopsis

Vinyl halides can be coupled by NiCRA-bpy in THF or hexane. Interestingly simply changing the solvent changes the nature of the product : diene in THF, and enyne in hexane.

Metal promoted homocoupling of vinyl halides continues to be actively studied on account of its wide range of synthetic applications.

In connection with our investigations on Comnlex Reducing Agents (CRA)', i.e. mixtures prepared in situ of sodium hydride, alkoxide, -nickel acetate and 2,2'-binyridyl, we have previously reported 3 that &ONa-NiCRA-bpy (Note)

were convenient reagents for coupling aryl and vinyl halides. We found that

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The preparation of NiCRA (NaH-B:ONa-Ni(OAc) ) in the oresence of PPh3 leads to a reagent (termed NiCRA-PPh3) which is shown $ o be one of the most efflclent Ni containing reagents reported so far for the homocoupling of heteroaromatic halides. Symmetrical couDling of aryl halides may be performed wi