Amidoboronates: bringing together the synthesis of BN-heterocycles via a reductive coupling and dynamic covalent chemistry

Abstract

This Perspective describes how amidoboronates open up new chemical space spanning the areas of BN-heterocycles and dynamic covalent chemistry. BN-containing heterocycles offer the potential to access new properties and reactivity compared to their C–C analogues. Amidoboronates are introduced as a new class of B–N heterocycles that can be synthesised in three isomeric forms (meso₅, rac₅ and rac₆) from the reductive coupling of N-aryl iminoboronates. Furthermore, initial investigations on the dynamic covalent chemistry of amidoboronates are discussed, such as the reversibility of C–C bond formation following the reductive coupling and tuning the rac₅/rac₆ ratio via dynamic covalent B–N and B–O bonds.