title: An S(N)Ar approach to sterically hindered ortho-alkoxybenzaldehydes for the synthesis of olefin metathesis catalysts.
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.
authors.affiliation: Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
authors.forename: Keary M
authors.initials: KM
authors.lastname: Engle
authors.affiliation: Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
authors.forename: Shao-Xiong
authors.initials: SX
authors.lastname: Luo
authors.affiliation: Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
authors.forename: Robert H
authors.initials: RH
authors.lastname: Grubbs
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D001128:Argon / Q000737:chemistry*; D001547:Benzaldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002614:Chelating Agents; D018360:Crystallography, X-Ray; D013343:Styrenes / Q000737:chemistry*
chemical_list: D000475:Alkenes; D001547:Benzaldehydes; D002614:Chelating Agents; D013343:Styrenes; D001128:Argon