We report the iron-catalyzed C–H alkylative ring openings of oxabicyclic alkenes by chelation assistance. The method converted a broad family of benzamides into highly functionalized dihydronaphthen-2-ol derivatives, amenable to further synthetic transformations by removing the triazole directing group. Remarkably, the iron catalysis displayed complete chemo- and regioselectivities in converting oxabicyclic alkenes functionalized at the bridgehead carbons. Mechanistic investigations, by means of DFT calculations, fully elucidated the mechanism of the iron catalysis.
Iron-Catalyzed C–H Alkylative Ring Openings of Oxabicyclic Alkenes / Serafino, A., Barocelli, E., Secchi, A., Pezzato, C., Ackermann, L., Santoro, S., Cera, G.. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 28:2(2026), pp. 691-696. [10.1021/acs.orglett.5c04816]
Iron-Catalyzed C–H Alkylative Ring Openings of Oxabicyclic Alkenes
Serafino A.;Barocelli E.;Secchi A.;Cera G.
2026-01-01
Abstract
We report the iron-catalyzed C–H alkylative ring openings of oxabicyclic alkenes by chelation assistance. The method converted a broad family of benzamides into highly functionalized dihydronaphthen-2-ol derivatives, amenable to further synthetic transformations by removing the triazole directing group. Remarkably, the iron catalysis displayed complete chemo- and regioselectivities in converting oxabicyclic alkenes functionalized at the bridgehead carbons. Mechanistic investigations, by means of DFT calculations, fully elucidated the mechanism of the iron catalysis.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
