Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Regioselective Diversification of 2,1-Borazaronaphthalenes: Unlocking Isosteric Space via C–H Activation

Regioselective Diversification of 2,1-Borazaronaphthalenes: Unlocking Isosteric Space via C–H Activation
Casey Howshall, Geraint H. M. Davies, Borna Saeednia, Gary A. Molander, Matthieu Jouffroy, Fatemeh Sherafat
Methods for the regioselective C–H borylation and subsequent cross-coupling of the 2,1-borazaronaphthalene core are reported. Azaborines are dependent on B–N/C═C isosterism when employed in strategies for developing diverse heterocyclic scaffolds. Although 2,1-borazaronaphthalene is closely related to naphthalene in terms of structure, the argument is made that the former has electronic similarities to indole. Based on that premise, iridium-mediated C–H activation has enabled facile installation of a versatile, nucleophilic coupling handle at a previously inaccessible site of 2,1-borazaronaphthalenes. A variety of substituted 2,1-borazaronaphthalene cores can be successfully borylated and further cross-coupled in a facile manner to yield diverse C(8)-substituted 2,1-borazaronaphthalenes.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01331

DOI: 10.1021/acs.joc.7b01331

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