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Published April 17, 2015 | Supplemental Material
Journal Article Open

An S_NAr Approach to Sterically Hindered ortho-Alkoxybenzaldehydes for the Synthesis of Olefin Metathesis Catalysts


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.

Additional Information

© 2015 American Chemical Society. Received: March 12, 2015. Publication Date (Web): March 31, 2015. The research described in this paper was supported financially by the Office of Naval Research (Award Number N00014-12-1-0596) and the National Institutes of Health NIGMS (Award Number F32GM108145; postdoctoral fellowship to K.M.E.). Prof. Jeffrey S. Cannon (Occidental College) and Dr. Sarah M. Bronner (Genentech) are gratefully acknowledged for helpful discussions. The content is solely the responsibility of the authors and does not necessarily represent the official views of the Office of Naval Research or the National Institutes of Health.

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