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

Tae Bo Sim; Jaesung Choi; Meyoung Ju Joung; Nung Min Yoon

doi:10.1021/jo961751f

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

Tae Bo Sim, Jaesung Choi, Meyoung Ju Joung, Nung Min Yoon

Research output: Contribution to journal › Article › peer-review

36 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 language	English
Pages (from-to)	2357-2361
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	62
Issue number	8
DOIs	https://doi.org/10.1021/jo961751f
Publication status	Published - 1997

ASJC Scopus subject areas

Organic Chemistry

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

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.",

author = "Sim, {Tae Bo} and Jaesung Choi and Joung, {Meyoung Ju} and Yoon, {Nung Min}",

year = "1997",

doi = "10.1021/jo961751f",

language = "English",

volume = "62",

pages = "2357--2361",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "8",

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T1 - A New Coupling Reaction of Alkyl Iodides with Electron Deficient Alkenes Nickel Boride (cat.) - Borohydride Exchange Resin in Methanol

AU - Sim, Tae Bo

AU - Choi, Jaesung

AU - Joung, Meyoung Ju

AU - Yoon, Nung Min

PY - 1997

Y1 - 1997

N2 - 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.

AB - 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.

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SN - 0022-3263

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 8

ER -

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

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