Rhodium-mediated assembly of new heterocycles: from borylenes to oxaboroles
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Date
2025
Authors
Hsiang, Shou-Jen
Hayes, Paul G.
Journal Title
Journal ISSN
Volume Title
Publisher
Wiley
Abstract
Base-stabilized rhodium borylene complex κ2-L(CO)Rh(BMes), 2; κ2-L=κ2-NN’-Rh,κ1-N−B-(2,5-[iPr2P=N(4-iPrC6H4)]2-N’(C4H2)−); Mes=mesityl, reacts with a series of alkynes (PhC≡C—R; R=Ph, Me, CO2Et, H) to yield unique structures whereby the alkyne has regioselectively added across boron and the carbon atom of a CO ligand. The resulting complexes, LRh[C(O)C(Ph)C(R)B(Mes)], 3R, react with additional CO to afford cycle-containing products, L(CO)Rhmathematical equation ), 5R, that ultimately release highly functionalized organic heterocycles of the form mathematical equation =NPipp (Pipp=4-iPrC6H4), 6. These oxaboroles, which were assembled from a primary hydroborane, CO, an alkyne, and an azide-generated NPipp, are structurally analogous to two of the five boron-containing therapeutics approved by the FDA.
Description
Open access article. Creative Commons Attribution 4.0 International license (CC BY 4.0) applies
Keywords
Cyclization , Alkyne , Borylene , Rhodium , Oxaborale
Citation
Hsiang, S.-J., & Hayes, Paul G. (2025). Rhodium-mediated assembly of new heterocycles: From borylenes to oxaboroles. Angewandte Chemie Int. Ed., 64(10), Article e202421, https://doi.org/10.1002/anie.202421302302