Unearthing the
Subtleties of Rhodium(II)-Catalyzed
Carbenoid Cycloadditions to Furans with an N‑Sulfonyl-1,2,3-triazole
Probe

Bettencourt, Christian
J.; Krainz, Tanja; Chow, Sharon; Parr, Brendan T.; Tracy, William F.; Bernhardt, Paul V.; Davies, Huw M. L.; Williams, Craig M.

doi:10.1021/acs.orglett.2c03869.s001

ol2c03869_si_001.pdf (5.08 MB)

Unearthing the Subtleties of Rhodium(II)-Catalyzed Carbenoid Cycloadditions to Furans with an N‑Sulfonyl-1,2,3-triazole Probe

journal contribution

posted on 2022-12-13, 16:42 authored by Christian J. Bettencourt, Tanja Krainz, Sharon Chow, Brendan T. Parr, William F. Tracy, Paul V. Bernhardt, Huw M. L. Davies, Craig M. Williams

The rhodium(II)-catalyzed reaction of a model alkenyl donor/acceptor N-sulfonyltriazole with a wide selection of furans is reported. This investigation unearthed a range of structurally diverse carbocyclic and ring-opened products, in good to excellent yields. The products obtained are proposed to arise selectively via cyclopropanation or zwitterionic rearrangement pathways, which are highly dependent on both the structural and electronic features of the furan substrate.