Catalytic B–C Coupling by Si/B Exchange: A Versatile Route to π-Conjugated Organoborane Molecules, Oligomers, and Polymers

• DOI: 10.1021/jacs.7b01835
• Publication Date: 2017-04-10T17:44:52Z
• Authors: Artur Lik; Lars Fritze; Lars Müller; Holger Helten
• Keywords: Organosilicon

Conjugated organoboranes have emerged as attractive hybrid materials for optoelectronic applications. Herein, a highly efficient, environmentally benign catalytic B-C bond formation method is presented that uses organosilicon compounds, dibromoboranes, and the metal-free organocatalyst Me3SiNTf2. This Si/B exchange approach has been successfully applied to synthesis of arylborane molecules 4a-c, oligomers 8a,b, polymers 8a',b'. Photophysical investigations, supported by TD-DFT calculations, reveal effective π-conjugation in thienyl- furylborane species; latter are also emissive.