Rhenium-Catalyzed Cyclization via 1,2-Iodine and 1,5-Hydrogen Migration for the Synthesis of 2‑Iodo‑1H‑indenes

A rhenium complex catalyzed the formation of 2-iodo-1H-indene derivatives through iodine and hydrogen migration of 3-iodopropargyl ethers. The reaction proceeded via generation of 1-iodoalkenylrhenium carbene species by sequential 1,2-iodine and 1,5-hydrogen shifts with readily available precursors...

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Veröffentlicht in:Organic letters 2019-09, Vol.21 (17), p.6756-6760
Hauptverfasser: Murai, Masahito, Takai, Kazuhiko
Format: Artikel
Sprache:eng
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Zusammenfassung:A rhenium complex catalyzed the formation of 2-iodo-1H-indene derivatives through iodine and hydrogen migration of 3-iodopropargyl ethers. The reaction proceeded via generation of 1-iodoalkenylrhenium carbene species by sequential 1,2-iodine and 1,5-hydrogen shifts with readily available precursors under neutral conditions. The reaction mechanism and the reactivity of the generated alkenylcarbene species were also investigated.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02380