Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 15, Pages 8537-8541Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202016268
Keywords
catalysis; heteroarenes; hydroarylation; silver; styrenes
Categories
Funding
- Deutsche Forschungsgemeinschaft [CRC 1459, SFB 858, IRTG 2027]
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The research presents a mild and general catalytic system for the selective hydroheteroarylation of multiply substituted styrenes and heteroaromatic styrenes. The discovery of commercially available 2,2':5',2''-terthiophene as a key reagent opens up potential significant applications in organic synthesis.
Hydroarylation is an effective strategy to rapidly increase the complexity of organic structures by transforming flat alkene moieties into three-dimensional frameworks. Many strategies have already been developed to achieve the hydroarylation of styrenes, however most of these reports examine the hydroarylation of unpolar, beta-mono- or beta-unsubstituted styrenes, while exploring mainly electron-rich benzene nucleophiles. Herein, we report a mild and general catalytic system for the selective hydroheteroarylation of multiply substituted styrenes and heteroaromatic styrenes. Mechanistic analysis of the reaction led to the discovery of commercially available 2,2 ':5 ',2 ''-terthiophene as a key reagent.
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