Abstract
A copper-catalyzed decarboxylative elimination reaction of (hetero)aromatic propionic acids to vinyl (hetero)arenes has been developed. This method furnishes alkenes from carboxylic acids without the need for stochiometric Pb or Ag additives or expensive or specialized photocatalysts. A series of mechanistic experiments indicate that the reaction proceeds via benzylic deprotonation and subsequent radical decarboxylation; a pathway that is distinct from the single-electron-transfer mechanisms implicated in related decarboxylative elimination reactions.
Original language | English (US) |
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Pages (from-to) | 1713-1719 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 88 |
Issue number | 3 |
DOIs | |
State | Published - Feb 3 2023 |
Externally published | Yes |
Bibliographical note
Funding Information:We are grateful to West Virginia University and the NSF (CHE-2102538) for financial support of this work. NMR spectroscopy facilities were partially supported by the NSF (CHE-1228336).
Publisher Copyright:
© 2023 American Chemical Society.
PubMed: MeSH publication types
- Journal Article