Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 44, Pages 16376-16379Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja4095878
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Funding
- National Science Foundation through the CCI Center for Selective C-H Functionalization [CHE-1205646]
- National Science Foundation through the PREM program [DMR-0934212]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1205646] Funding Source: National Science Foundation
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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.
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