Controllable direct arylation: fast route to symmetrical and unsymmetrical 4,7-diaryl-5,6-difluoro-2,1,3-benzothiadiazole derivatives for organic optoelectronic materials

Junxiang Zhang; Wayne Chen; Anthony J Rojas; Evgheni V Jucov; Tatiana V Timofeeva; Timothy C Parker; Stephen Barlow; Seth R Marder

doi:10.1021/ja4095878

Controllable direct arylation: fast route to symmetrical and unsymmetrical 4,7-diaryl-5,6-difluoro-2,1,3-benzothiadiazole derivatives for organic optoelectronic materials

J Am Chem Soc. 2013 Nov 6;135(44):16376-9. doi: 10.1021/ja4095878.

Authors

Junxiang Zhang, Wayne Chen, Anthony J Rojas, Evgheni V Jucov, Tatiana V Timofeeva, Timothy C Parker, Stephen Barlow, Seth R Marder

PMID: 24164538
DOI: 10.1021/ja4095878

Abstract

Arylation in the 4- and 7-positions of 2,1,3-benzothiadiazole (BT) and its monofluoro- (MFBT) and difluoro- (DFBT) derivatives by (hetero)aryl bromides using Pd-catalyzed C–H activation has been investigated. MFBT and DFBT can be diarylated in moderate to high yields (up to 96% for DFBT) by a variety of aryl bromides. DFBT can be sequentially arylated using two different aryl bromides to give differentially substituted DFBT derivatives. The moderate to high yields of doubly arylated MFBT and DFBT and the ability to obtain differentially substituted products can be applied to a variety of organic photonic and electronic materials.