Dimeric boroles: effective sources of monomeric boroles for heterocycle synthesis.

ABSTRACT: Monomeric boroles have been gaining attention as reagents for the synthesis of heterocycles due to their ability to insert atoms into the BC₄ ring in a single step. Although unique boron frameworks can be accessed via this methodology, the products feature aryl substitution on the carbon centers as steric bulk is required to preclude borole dimerization. This work demonstrates that insertion chemistry is possible with Diels-Alder dimeric boroles and that such reactivity is not exclusive to monomeric boroles with bulky groups. With 1-phenyl-2,3,4,5-tetramethylborole dimer, the formal 1,1-insertion of a nitrene and sulfur generate the six-membered aromatic 1,2-azaborine and 1,2-thiaborine, respectively. The isolation of the 1,2-thiaborine enabled the synthesis of an η⁶

SUBMITTER: Su X 

PROVIDER: S-EPMC7012074 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature