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An Expedient Route to Substituted Furans via Olefin Cross-Metathesis

The olefin cross-metathesis (CM) reaction is used extensively in organic chemistry and represents a powerful method for the selective synthesis of differentially substituted alkene products. Surprisingly, efforts to integrate this remarkable process into strategies for aromatic and heteroaromatic co... Full description

Journal Title: Proceedings of the National Academy of Sciences of the United States of America 1 February 2010, Vol.107(8), pp.3373-3376
Main Author: Donohoe, Timothy J.
Other Authors: Bower, John F. , Halpern, Jack
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 00278424 ; DOI: 10.1073/pnas.0913466107
Link: https://www.jstor.org/stable/40537293
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recordid: jstor_archive_2340537293
title: An Expedient Route to Substituted Furans via Olefin Cross-Metathesis
format: Article
creator:
  • Donohoe, Timothy J.
  • Bower, John F.
  • Halpern, Jack
subjects:
  • Physical sciences -- Chemistry -- Chemical compounds
  • Physical sciences -- Chemistry -- Chemical reactions
  • Physical sciences -- Chemistry -- Chemical compounds
  • Physical sciences -- Chemistry -- Chemical compounds
  • Physical sciences -- Chemistry -- Chemical reactions
  • Physical sciences -- Chemistry -- Chemical compounds
  • Physical sciences -- Chemistry -- Chemical compounds
  • Physical sciences -- Chemistry -- Chemical elements
  • Mathematics -- Pure mathematics -- Geometry
  • Physical sciences -- Chemistry -- Organic chemistry
  • Physical sciences -- Chemistry -- Chemical compounds
  • Physical sciences -- Chemistry -- Chemical reactions
  • Physical sciences -- Chemistry -- Chemical compounds
  • Physical sciences -- Chemistry -- Chemical compounds
  • Physical sciences -- Chemistry -- Chemical reactions
  • Physical sciences -- Chemistry -- Chemical compounds
  • Physical sciences -- Chemistry -- Chemical compounds
  • Physical sciences -- Chemistry -- Chemical elements
  • Mathematics -- Pure mathematics -- Geometry
  • Physical sciences -- Chemistry -- Organic chemistry
ispartof: Proceedings of the National Academy of Sciences of the United States of America, 1 February 2010, Vol.107(8), pp.3373-3376
description: The olefin cross-metathesis (CM) reaction is used extensively in organic chemistry and represents a powerful method for the selective synthesis of differentially substituted alkene products. Surprisingly, efforts to integrate this remarkable process into strategies for aromatic and heteroaromatic construction have not been reported. Such structures represent key elements of the majority of small molecule drug compounds; methods for the controlled preparation of highly substituted derivatives are essential to medicinal chemistry. Here we show that the olefin CM reaction, in combination with an acid cocatalyst or subsequent Heck arylation, provides a concise and flexible entry to 2,5-di-or 2,3,5-tri-substituted furans. These cascade processes portend further opportunities for the regiocontrolled preparation of other highly substituted aromatic and heteroaromatic classes.
language: eng
source:
identifier: ISSN: 00278424 ; DOI: 10.1073/pnas.0913466107
fulltext: fulltext
issn:
  • 0027-8424
  • 00278424
url: Link


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titleAn Expedient Route to Substituted Furans via Olefin Cross-Metathesis
creatorDonohoe, Timothy J. ; Bower, John F. ; Halpern, Jack
ispartofProceedings of the National Academy of Sciences of the United States of America, 1 February 2010, Vol.107(8), pp.3373-3376
identifierISSN: 00278424 ; DOI: 10.1073/pnas.0913466107
subjectPhysical sciences -- Chemistry -- Chemical compounds ; Physical sciences -- Chemistry -- Chemical reactions ; Physical sciences -- Chemistry -- Chemical compounds ; Physical sciences -- Chemistry -- Chemical compounds ; Physical sciences -- Chemistry -- Chemical reactions ; Physical sciences -- Chemistry -- Chemical compounds ; Physical sciences -- Chemistry -- Chemical compounds ; Physical sciences -- Chemistry -- Chemical elements ; Mathematics -- Pure mathematics -- Geometry ; Physical sciences -- Chemistry -- Organic chemistry ; Physical sciences -- Chemistry -- Chemical compounds ; Physical sciences -- Chemistry -- Chemical reactions ; Physical sciences -- Chemistry -- Chemical compounds ; Physical sciences -- Chemistry -- Chemical compounds ; Physical sciences -- Chemistry -- Chemical reactions ; Physical sciences -- Chemistry -- Chemical compounds ; Physical sciences -- Chemistry -- Chemical compounds ; Physical sciences -- Chemistry -- Chemical elements ; Mathematics -- Pure mathematics -- Geometry ; Physical sciences -- Chemistry -- Organic chemistry
descriptionThe olefin cross-metathesis (CM) reaction is used extensively in organic chemistry and represents a powerful method for the selective synthesis of differentially substituted alkene products. Surprisingly, efforts to integrate this remarkable process into strategies for aromatic and heteroaromatic construction have not been reported. Such structures represent key elements of the majority of small molecule drug compounds; methods for the controlled preparation of highly substituted derivatives are essential to medicinal chemistry. Here we show that the olefin CM reaction, in combination with an acid cocatalyst or subsequent Heck arylation, provides a concise and flexible entry to 2,5-di-or 2,3,5-tri-substituted furans. These cascade processes portend further opportunities for the regiocontrolled preparation of other highly substituted aromatic and heteroaromatic classes.
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abstractThe olefin cross-metathesis (CM) reaction is used extensively in organic chemistry and represents a powerful method for the selective synthesis of differentially substituted alkene products. Surprisingly, efforts to integrate this remarkable process into strategies for aromatic and heteroaromatic construction have not been reported. Such structures represent key elements of the majority of small molecule drug compounds; methods for the controlled preparation of highly substituted derivatives are essential to medicinal chemistry. Here we show that the olefin CM reaction, in combination with an acid cocatalyst or subsequent Heck arylation, provides a concise and flexible entry to 2,5-di-or 2,3,5-tri-substituted furans. These cascade processes portend further opportunities for the regiocontrolled preparation of other highly substituted aromatic and heteroaromatic classes.
pubNational Academy of Sciences
doi10.1073/pnas.0913466107
eissn10916490
date2010-02-23