Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 15, Pages 5090-5094Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201900166
Keywords
allenylation; C-H activation; Diels-Alder reactions; directing groups; Manganese
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Funding
- NSFC [21525208]
- Fundamental Research Funds for the Central Universities [GK201903028]
- SNNU
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Pyridines/pyrimidines are common and effective directing groups in C-H activation. However, they are poorly functionalizable heteroarenes. Reported in this work is Mn-catalyzed dehydrocyanative transannulation between three classes of heteroarenes and propargyl carbonates. The pyridyl/pyrimidyl groups in the heteroarenes initially function as directing groups to enable C-H allenylation; they then undergo intramolecular Diels-Alder/retro-Diels-Alder reactions with the allene moiety to afford fused carbo/heterocycles. Three key intermediates at different stages of the reaction were isolated.
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