Selective alkylation and Suzuki coupling as an efficient strategy for introducing functional anchors to the ethylene-bis(indenyl) ligand |
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Authors: | Anthony P. Panarello |
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Affiliation: | Department of Chemical and Biochemical Engineering, Rutgers, The State University of New Jersey, 98, Brett Road, Piscataway, NJ 08854, USA |
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Abstract: | Chiral ansa-ethylene-bis(indenyl)-metal complexes, EBI-MX2, are useful pre-catalysts for a wide variety of reactions, including hydrogenations, hydrosilylations, and polymerization reactions. In order to immobilize these complexes onto heterogeneous supports, a new methodology was developed to introduce functional anchors to the ethylene-bis(indenyl) ligand, EBI. This was accomplished by selective alkylation of indene to form toluene-4-sulfonic acid 2-(3H-inden-1-yl)-ethyl ester, which was then used to alkylate 6-bromoindene. The selective introduction of an aryl bromide then undergoes coupling reactions with aryl borates via the Suzuki coupling to efficiently introduce an alkenyl or alcohol, functional anchor in a simple four step synthesis. |
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Keywords: | Suzuki coupling Selective alkylation Indene Ligand Cyclopaentadienyl Ethylene-bis(indene) |
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