Hayes, Paul

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Rhodium-mediated assembly of new heterocycles: from borylenes to oxaboroles
(Wiley, 2025) Hsiang, Shou-Jen; Hayes, Paul G.
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.