Six-Membered Rings With Two or More Heteroatoms With at Least One Boron

Abstract

A survey of the chemical literature published between 2008 and 2018 dealing with the synthesis, structural investigations and chemical reactivity of six-membered boracycles with two or more heteroatoms is presented. The chapter outlines the advances in the chemistry of monocyclic, fused and polycyclic species and should be read in conjunction with earlier chapters in CHEC I (1984, vol. 1, p. 629), CHEC II (1996, vol. 6, p. 1155) and CHEC III (2008, vol. 9, p. 961). Fully aromatic and both partially and fully reduced species are included. New routes to the synthesis of BN-isosteres of benzene, naphthalene and BN-polycyclic and ring-fused BN heteroaromatic compounds, including modern synthetic technique are described. The reactivity and substituent modification procedures are covered. Also included are sections on theoretical methods and thermodynamic aspects such as aromaticity and thermodynamic stability. Applications of polyheteroatom six-membered boracycles in material and medicinal chemistry are discussed.