Regiodivergent Carbonylation of Alkenes: Selective Palladium-Catalyzed Synthesis of Linear and Branched Selenoesters

Zhusong Cao, Qiang Wang, Helfried Neumann, Matthias Beller

Research output: Contribution to journalArticlepeer-review

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Abstract

An unprecedented regiodivergent palladium-catalyzed carbonylation of aromatic alkenes has been developed. Utilizing commercially available Pd(CH3CN)2Cl2 in the presence of 1,1′-ferrocenediyl-bis(tert-butyl(pyridin-2-yl)phosphine) ligand L8 diverse selenoesters are obtained in a straightforward manner. Key to success for the control of the regioselectivity of the carbonylation step is the concentration of the acidic co-catalyst. This general protocol features wide functional group compatibility and good regioselectivity. Mechanistic studies suggest that the presence of stoichiometric amounts of acid changes the properties and coordination mode of the ligand leading to reversed regioselectivity.

Original languageEnglish
Article numbere202313714
JournalAngewandte Chemie International Edition in English
Volume63
Issue number2
DOIs
StatePublished - 8 Jan 2024
Externally publishedYes

Keywords

  • Carbonylation
  • P Ligands
  • Palladium
  • Regioselectivity
  • Selenoesters

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