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An S(N)Ar approach to sterically hindered ortho-alkoxybenzaldehydes for the synthesis of olefin metathesis catalysts

Academic Article
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Overview

authors

  • Engle, Keary M.
  • Luo, S. X.
  • Grubbs, R. H.

publication date

  • April 2015

journal

  • Journal of Organic Chemistry  Journal

abstract

  • A three-step procedure has been developed for preparing ortho-alkoxybenzaldehydes from ortho-fluorobenzaldehydes that tolerates the use of sterically hindered sodium alkoxide nucleophiles. The protocol is modular and operationally convenient. The ortho-alkoxybenzaldehyde products can be converted in one additional step to ortho-alkoxystyrenes by a Wittig reaction. These styrenes are precursors to the chelating benzylidene moiety in a proposed series of novel ruthenium complexes for use in olefin metathesis. Chelation with three representative styrenes has been demonstrated.

subject areas

  • Alkenes
  • Argon
  • Benzaldehydes
  • Catalysis
  • Chelating Agents
  • Crystallography, X-Ray
  • Styrenes
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Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/acs.joc.5b00563

PubMed ID

  • 25826714
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Additional Document Info

start page

  • 4213

end page

  • 4220

volume

  • 80

issue

  • 8

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