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Nickel-catalyzed regiodivergent opening of epoxides with aryl halides: co-catalysis controls regioselectivity

Epoxides are versatile intermediates in organic synthesis, but have rarely been employed in cross-coupling reactions. We report that bipyridine-ligated nickel can mediate the addition of functionalized aryl halides, a vinyl halide, and a vinyl triflate to epoxides under reducing conditions. For term... Full description

Journal Title: Journal of the American Chemical Society 08 January 2014, Vol.136(1), pp.48-51
Main Author: Zhao, Yang
Other Authors: Weix, Daniel J
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1520-5126 ; PMID: 24341892 Version:1 ; DOI: 10.1021/ja410704d
Link: http://pubmed.gov/24341892
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recordid: medline24341892
title: Nickel-catalyzed regiodivergent opening of epoxides with aryl halides: co-catalysis controls regioselectivity
format: Article
creator:
  • Zhao, Yang
  • Weix, Daniel J
subjects:
  • Epoxy Compounds -- Chemistry
  • Halogens -- Chemistry
  • Nickel -- Chemistry
ispartof: Journal of the American Chemical Society, 08 January 2014, Vol.136(1), pp.48-51
description: Epoxides are versatile intermediates in organic synthesis, but have rarely been employed in cross-coupling reactions. We report that bipyridine-ligated nickel can mediate the addition of functionalized aryl halides, a vinyl halide, and a vinyl triflate to epoxides under reducing conditions. For terminal epoxides, the regioselectivity of the reaction depends upon the cocatalyst employed. Iodide cocatalysis results in opening at the less hindered position via an iodohydrin intermediate. Titanocene cocatalysis results in opening at the more hindered position, presumably via Ti(III)-mediated radical generation. 1,2-Disubstituted epoxides are opened under both conditions to form predominantly the trans product.
language: eng
source:
identifier: E-ISSN: 1520-5126 ; PMID: 24341892 Version:1 ; DOI: 10.1021/ja410704d
fulltext: fulltext
issn:
  • 15205126
  • 1520-5126
url: Link


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titleNickel-catalyzed regiodivergent opening of epoxides with aryl halides: co-catalysis controls regioselectivity
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subjectEpoxy Compounds -- Chemistry ; Halogens -- Chemistry ; Nickel -- Chemistry
descriptionEpoxides are versatile intermediates in organic synthesis, but have rarely been employed in cross-coupling reactions. We report that bipyridine-ligated nickel can mediate the addition of functionalized aryl halides, a vinyl halide, and a vinyl triflate to epoxides under reducing conditions. For terminal epoxides, the regioselectivity of the reaction depends upon the cocatalyst employed. Iodide cocatalysis results in opening at the less hindered position via an iodohydrin intermediate. Titanocene cocatalysis results in opening at the more hindered position, presumably via Ti(III)-mediated radical generation. 1,2-Disubstituted epoxides are opened under both conditions to form predominantly the trans product.
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titleNickel-catalyzed regiodivergent opening of epoxides with aryl halides: co-catalysis controls regioselectivity
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abstractEpoxides are versatile intermediates in organic synthesis, but have rarely been employed in cross-coupling reactions. We report that bipyridine-ligated nickel can mediate the addition of functionalized aryl halides, a vinyl halide, and a vinyl triflate to epoxides under reducing conditions. For terminal epoxides, the regioselectivity of the reaction depends upon the cocatalyst employed. Iodide cocatalysis results in opening at the less hindered position via an iodohydrin intermediate. Titanocene cocatalysis results in opening at the more hindered position, presumably via Ti(III)-mediated radical generation. 1,2-Disubstituted epoxides are opened under both conditions to form predominantly the trans product.
doi10.1021/ja410704d
pmid24341892
date2014-01-08