Details

Autor(en) / Beteiligte

• Coles-Taylor, Brandon L.
• Ellinwood, Mitchell L.
• McCallum, Maximilian S.
• McCormack, Sara L.
• Jones, Meredith H.
• Muñoz, Andrés G.
• Michel, Brian W.

Titel

Access to Substituted Indenol Ethers via a Regioselective Intermolecular Carbopalladation Cascade

Ist Teil von

• Journal of organic chemistry, 2022-12, Vol.87 (24), p.16517-16525

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2022

Quelle

MEDLINE

Beschreibungen/Notizen

• Alkyne carbopalladation reactions can rapidly generate multiple new C–C bonds; however, regioselectivity is challenging for intermolecular variants. Using ynol ethers, we observe complete regiocontrol of migratory insertion followed by a second migratory insertion with a pendant alkene to turn-over the catalytic cycle. The resulting products are oligosubstituted 1-indenol ethers with defined stereochemistry based on the initial alkene geometry. Blocking β-hydride elimination allowed for C–H and C–C reductive elimination steps for catalyst turnover.