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May 2, 20265 citations

Decarboxylative alkylation of alkenes.

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TRTriptesh Kumar RoyFTFederico Maria TamboriniRPRoland Petzold

Key Points

  • To explore a new method for regio- and diastereoselective C-H alkylation of alkenes using carboxylic acids.
  • Developed a unique polar decarboxylative alkylation process.
  • Utilized persistent alkylzinc intermediates from redox-active esters.
  • Employed Pd-catalysed cross-coupling with alkenyl thianthrenium salts.
  • Successfully formed substituted alkenes with high diastereoselectivity.
  • Achieved alkylation with various alkyl groups on different types of alkenes.
  • Demonstrated effectiveness across cyclic, acyclic, terminal, internal, and substituted alkenes.

Abstract

. Here we report a formal regio- and diastereoselective C-H alkylation of alkenes with carboxylic acids as alkyl source, readily available in large diversity. Key to the development is a polar decarboxylative alkylation that deviates from the current model of radical-mediated C-C bond formation from carboxylic acid derivatives, enabled by a previously unappreciated access to persistent alkylzinc intermediates from redox-active esters. A Pd-catalysed cross-coupling of the alkylzinc species with alkenyl thianthrenium salts accessed from alkenes affords the substituted alkenes in high diastereoselectivity. The transformation offers alkylation of cyclic, acyclic, terminal, internal, mono-substituted, di-substituted and tri-substituted alkenes with diverse alkyl groups.

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Cite This Study

Roy et al. (2026) studied this question.

synapsesocial.com/papers/69f594e171405d493afffcb6https://doi.org/10.1038/s41586-026-10463-1
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