One tool to bring them all: Au-catalyzed synthesis of B,O- and B,N-doped PAHs from boronic and borinic acids.

ABSTRACT: The isoelectronic replacement of C[double bond, length as m-dash]C bonds with ^-B[double bond, length as m-dash]N⁺ bonds in polycyclic aromatic hydrocarbons (PAHs) is a widely used tool to prepare novel optoelectronic materials. Far less well explored are corresponding B,O-doped PAHs, although they have a similarly high application potential. We herein report on the modular synthesis of B,N- and B,O-doped PAHs through the [Au(PPh₃)NTf₂]-catalyzed 6-endo-dig cyclization of BN-H and BO-H bonds across suitably positioned C[triple bond, length as m-dash]C bonds in the key step. Readily available, easy-to-handle o-alkynylaryl boronic and borinic acids serve as starting materials, which are either cyclized directly or first converted into

SUBMITTER: Ouadoudi O 

PROVIDER: S-EPMC8179653 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature