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.

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dc.contributor.authorPiers, Warren E.
dc.contributor.authorMorgan, Matthew M.
dc.contributor.authorPatrick, Evan A.
dc.contributor.authorRautiainen, J. Mikko
dc.contributor.authorTuononen, Heikki M.
dc.contributor.authorSpasyuk, Denis M.
dc.date.accessioned2017-11-03T18:49:19Z
dc.date.available2017-11-03T18:49:19Z
dc.date.issued2017-03-08
dc.description.abstractA 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.en_US
dc.description.refereedYesen_US
dc.identifier.citationOrganometallics 2017, 36, 2541-2551en_US
dc.identifier.doihttp://dx.doi.org/10.11575/PRISM/30260
dc.identifier.urihttp://hdl.handle.net/1880/52233
dc.language.isoenen_US
dc.publisherAmerican Chemical Societyen_US
dc.publisher.departmentChemistryen_US
dc.publisher.facultyScienceen_US
dc.publisher.institutionUniversity of Calgaryen_US
dc.titleZirconocene-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.en_US
dc.typejournal article
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