Iridium-Catalyzed γ-Hydro(hetero)arylation of α,β-Unsaturated Amides

Fuente: PubMed "industrial biotechnology"
Org Lett. 2025 Dec 16. doi: 10.1021/acs.orglett.5c04961. Online ahead of print.ABSTRACTα,β-Unsaturated amides are versatile building blocks in organic synthesis; however, forging C-C bonds at the γ-position is considerably more challenging than conventional β-addition. Herein, we report an iridium-catalyzed γ-hydro(hetero)arylation of α,β-unsaturated amides that delivers γ-adducts with high regioselectivity. Mechanistic experiments support an initial alkene isomerization to a β,γ-unsaturated intermediate, followed by γ-selective hydro(hetero)arylation. The coordinating amide functionality is essential for both reactivity and selectivity, enabling reactions with indoles and an electron-rich arene.PMID:41401201 | DOI:10.1021/acs.orglett.5c04961