cs6b01936_si_001.pdf (6.24 MB)
Synthesis of Cyclopentadienols by Rhodium-Catalyzed C–H Activation of 8‑Formylquinolines and [2+2+1] Carbocyclization with Alkynes
journal contribution
posted on 2016-08-23, 00:00 authored by Xingwei Li, Xifa Yang, Zisong QiAn efficient Rh(III)-catalyzed redox-neutral
[2+2+1] coupling between
8-formylquinolines and alkynes has been realized for the synthesis
of cyclopentadienols with broad substrate scope and functional group
tolerance. The reaction occurs via C (acyl)–H activation with
double insertion of the alkyne in high atom-economy. Instead of simply
undergoing a [2+2+1] cyclization, a subsequent formal intermolecular
1,5-shift of the hydroxyl group is involved, which affords a thermodynamically
more stable, conjugated cyclopentadienol.