A New Coupling Reaction of Alkyl Iodides with Electron Deficient Alkenes Using Nickel Boride (cat.)−Borohydride Exchange Resin in Methanol

The radical addition reaction of alkyl iodides with α,β-unsaturated esters, nitriles, and ketones proceeds in moderate to excellent yields (50−95%) using Ni(OAc)2 (0.05−0.2 equiv)−BER (3−5 equiv) in methanol in 1−9 h at room temperature or at 65 °C. Nickel boride on borohydride exchange resin (BER)...

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Bibliographic Details
Published in:Journal of organic chemistry 1997-04, Vol.62 (8), p.2357-2361
Main Authors: Sim, Tae Bo, Choi, Jaesung, Joung, Meyoung Ju, Yoon, Nung Min
Format: Article
Language:English
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Summary:The radical addition reaction of alkyl iodides with α,β-unsaturated esters, nitriles, and ketones proceeds in moderate to excellent yields (50−95%) using Ni(OAc)2 (0.05−0.2 equiv)−BER (3−5 equiv) in methanol in 1−9 h at room temperature or at 65 °C. Nickel boride on borohydride exchange resin (BER) is a good alternative reagent to tributyltin hydride for the coupling of alkyl iodides with the electron deficient alkenes in methanol. Compared with tributyltin hydride method, this method has an advantage of simple workup, since nickel boride−BER can be removed readily by filtration.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo961751f