Although boroles (1) were first reported in 1969, their reactivity has remained virtually unexplored until recently. The unique combination of a Lewis acidic tricoordinate boron center, a diene, and a strained planar BC4 five-membered ring in a single molecule coupled with the four p-electron anti-aromatic state results in highly diverse reactivity for boroles.1 Our groups’ efforts have been focused on exploiting the chemistry of these species with the intent of utilizing boroles as reagents to generate six-, seven-, and eight-membered unsaturated boracycles (2–4).2 Conjugated boracycles are attractive synthetic targets as these species have applications in electronic devices and medicinal chemistry. Through these studies we have been able to prepare a diverse array heterocycles via the insertion of readily available substrates into boroles. This includes a new breed of benzene analogues (2) in which a C=C unit is replaced with boron and either a group 15 or group 16 element.3 The mechanisms of these reactions and properties of the boracycles will be discussed.
- J. H. Barnard, S. Yruegas, K. Huang, C. D. Martin, Chem. Commun., 2016, 52, 9985.
- a) K. Huang, C. D. Martin, Inorg. Chem., 2016, 55, 330. b) J. H. Barnard, S. Yruegas, S. A. Couchman, D. J. D. Wilson, J. L. Dutton, C. D. Martin, Organometallics, 2016, 35, 929. c) K. Huang, C. D. Martin, Inorg. Chem., 2015, 54, 1869. d) K. Huang, S. A. Couchman, D. J. D. Wilson, J. L. Dutton, C. D. Martin, Inorg. Chem., 2015, 54, 8957.
- a) J. H. Barnard, P. A. Brown, K. L. Shuford, C. D. Martin, Angew. Chem. Int. Ed., 2015, 54, 12083. b) S. A. Couchman, T. K. Thompson, D. J. D. Wilson, J. L. Dutton, C. D. Martin, Chem. Commun., 2014, 50, 11724. c) S. Yruegas, D. C. Patterson, C. D. Martin, Chem. Commun., 2016, 52, 11724. d) S. Yruegas, C. D. Martin, Chem. –Eur. J., 2016, 22, 18358.
Host: Paul Rupar