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

Jean-Marc Sotiropoulos (1) , Vadim D Romanenko (2)

1 IPREM - Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux
2 IBOPC - V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry

The literature on boron-containing heterocycles which have at least one other heteroatom within the six-membered ring system has been reviewed in the appropriate chapters of the first, second, and third editions of Comprehensive Heterocyclic Chemistry (CHECI-III) and in earlier reviews quoted therein.1–3 For the present edition, this chapter follows the same format as that used in CHEC-III and covers new developments reported from 2008. Since publication of CHEC-III, the field covered by this chapter has expanded enormously. The development is driven mainly by an extensive use of a BN/C=C isostere conception in the construction of a variety of novel boron-containing heteroπ-conjugated molecules. 4 The most common systems were studied to be 1, 2-, 1, 3-, and1,4-azaborines, 5–8 and their 1,2- and 1,4-oxaborine analogues9. A variety of π-extended BN-polycyclic aromatic hydrocarbons(PAHs) including BN-naphthalenes, BN-phenanthrenes, BN-anthracenes, BN-pyrene, BN-indenes, BN-coronenes, and higher BN-doped PAHs have also been synthesizedandwellcharacterized.10–121,9-dihydro-1,9-diboranaphthalenes and their fused analogues containing Hückel-anti-aromatic central B2C4 ring were also extensively covered in the literature.10 Finally, a large number of boracycles that contain heavy heteroatoms, such as S, Se, P, and Te, have been synthesized and studied during the past decade.7 A Chemical Abstracts search between 2008 and the end of 2018 revealed that the reare about 450 publications and more than 120 ring systems that come under the title of this article. The purpose of this survey is to summarize the most important data published over the last decade. Partially or totally saturated boracycles such as 1,3,2-diaza- or 1,2,3-dioxaboranes which were extensively covered in the first and second edition of Comprehensive Heterocyclic Chemistry are dealt with only briefly, as little new information is available beyond their standard preparative application. Borondipyrroles (BODIPY) and related chelate systems as well as substitution with BN units in cluster systems and graphitic materials are beyond the scope of this review.

Domaines: Chimie organique; Chimie

Jean-Marc Sotiropoulos, Vadim D Romanenko. Six-Membered Rings With Two or More Heteroatoms With at Least One Boron. Comprehensive Heterocyclic Chemistry, 9, pp.806-845., 2022, ⟨10.1016/B978-0-12-818655-8.00098-6⟩. ⟨hal-03256604⟩