Zirconocene-Based Methods for the Preparation of BN-Indenes : Application to the Synthesis of 1,5-Dibora-4a,8a-diaza-1,2,3,5,6,7-hexaaryl-4,8-dimethyl-s-indacenes
Morgan, M. M., Patrick, E. A., Rautiainen, J. M., Tuononen, H., Piers, W. E., & Spasyuk, D. M. (2017). Zirconocene-Based Methods for the Preparation of BN-Indenes : Application to the Synthesis of 1,5-Dibora-4a,8a-diaza-1,2,3,5,6,7-hexaaryl-4,8-dimethyl-s-indacenes. Organometallics, 36(14), 2541-2551. https://doi.org/10.1021/acs.organomet.7b00051
Julkaistu sarjassa
OrganometallicsTekijät
Päivämäärä
2017Oppiaine
Epäorgaaninen ja analyyttinen kemiaNanoscience CenterInorganic and Analytical ChemistryNanoscience CenterTekijänoikeudet
© 2017 American Chemical Society. This is a final draft version of an article whose final and definitive form has been published by ACS. Published in this repository with the kind permission of the publisher.
A method for the preparation of 3-bora-9-azaindene heterocycles based on zirconocene-mediated functionalization of the o-CH bonds of pyridines has been developed and used to make two such compounds. Unlike other methods, the boron center in these heterocycles remains functionalized with a chloride ligand, and so the compounds can be further elaborated through halide abstraction and reduction. The utility of the method was further demonstrated by applying it toward the preparation of 1,5-dibora-4a,8a-diaza BN analogues of the intriguing hydrocarbon s-indacene starting from 2,5-dimethylpyrazine. Gram quantities of one such compound were prepared and fully characterized, and both experimental and computational data are presented to compare its properties to those of the parent hydrocarbon s-indacene. These data indicate that the BN-substituted derivative exhibits lowered aromaticity in relation to the hydrocarbon.
Julkaisija
American Chemical SocietyISSN Hae Julkaisufoorumista
0276-7333Asiasanat
Julkaisu tutkimustietojärjestelmässä
https://converis.jyu.fi/converis/portal/detail/Publication/26898995
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Lisätietoja rahoituksesta
Funding for this work was provided by the NSERC of Canada (Discovery Grant) and the Canada Research Chair secretariat (Tier I CRC 2013–2020) to W.E.P. and the Academy of Finland (project #136929) and Emil Aaltonen Foundation to H.M.T. The Alexander von Humboldt Foundation (W.E.P.) is acknowledged for financial support. M.M.M. thanks the NSERC of Canada for PGSD Scholarship support.Samankaltainen aineisto
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