Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 5, Pages 1810-1815Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201506418
Keywords
carbenes; cobalt; fused-ring systems; heterocycles; porphyrinoids
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Funding
- National Natural Science Foundation of China [NSFC 21272197, 21472159]
- Hong Kong Research Grant Council [700813, 17306714]
- HKU
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A protocol on chemoselective cobalt(II) porphyrin-catalyzed intramolecular cyclopropanation of N-alkyl indoles/pyrroles with alkylcarbenes has been developed. The reaction enables the rapid construction of a range of nitrogen-containing polycyclic compounds in moderate to high yields from readily accessible materials. These N-containing polycyclic compounds can be converted into a variety of N-heterocycles with potential synthetic and biological interest. Compared to their N-tosylhydrazone counterparts, the use of bulky N-2,4,6-triisopropylbenzenesulfonyl hydrazones as carbene precursors allows cyclopropanation to occur under milder reaction conditions.
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