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

Taebo Sim, Jaesung Choi, Meyoung Ju Joung, Nung Min Yoon

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2357-2361
Number of pages5
JournalJournal of Organic Chemistry
Volume62
Issue number8
Publication statusPublished - 1997 Dec 1
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

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