Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 21, Pages 6309-6313Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201802539
Keywords
annulation; carboxylic acids; dearomatization; iridium catalysis; thiophenes
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Funding
- National NSF of China [21432005]
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The functionalization of thiophenes is a fundamental and important reaction. Herein, we disclose iridium-catalyzed one-pot annulation reactions of (benzo) thiophenes with (hetero) aromatic or alpha,beta-unsaturated carboxylic acids, which afford thiophene-fused coumarin-type frameworks. Dearomatization reactions of 2-substituted thiophenes with alpha,beta-unsaturated carboxylic acids deliver various thiophene-containing spirocyclic products. The occurrence of two interconnected reactions provides direct evidence for a Heck-type pathway. The mechanistic scenario described herein is distinctly different from the SEAr and concerted metalation-protodemetalation (CMD) pathways encountered in the well-described oxidative C-H/C-H cross-coupling reactions of thiophenes with other heteroarenes.
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