Access to Substituted Indenol Ethers via a Regioselective Intermolecular Carbopalladation Cascade
Brandon L Coles-Taylor1, Mitchell L Ellinwood1, Maximilian S McCallum1
1Department of Chemistry and Biochemistry, University of Denver, Denver, Colorado 80210, United States.
Abstract:
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.
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