4.7 Article

Visible-Light Photoredox Catalyzed Decarboxylative Alkylation of Vinylcyclopropanes

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 14, Pages 2340-2345

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202200227

Keywords

photoredox catalysis; decarboxylation; vinylcyclopropanes; alkylation; amino acids

Funding

  1. IISER Kolkata
  2. SERB
  3. DST-SERB
  4. UGC, IISER K
  5. DST

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This study presents a visible-light mediated photoredox catalyzed decarboxylative alkylation of vinylcyclopropanes using an Ir-based photocatalyst and Cs2CO3 as a base. Long-chained alkylated derivatives were obtained in moderate to high yields under mild reaction conditions without the need for external metal co-catalysts, oxidants, or additives. Various alkyl carboxylic acids and amino acid derivatives were used as alkylating reagents to synthesize gamma,delta-unsaturated diesters and unnatural homo-allylic amino acid derivatives with excellent functional groups tolerance. The method was further validated through gram-scale synthesis and a proposed mechanism based on control experiments and quenching studies.
Herein, we report a visible-light mediated photoredox catalyzed decarboxylative alkylation of vinylcyclopropanes. The reaction was carried out with an Ir-based photocatalyst and Cs2CO3 as a base. The desired functionalized long-chained alkylated derivatives were obtained in 48-93% yields under mild reaction conditions without any external metal co-catalysts, oxidants, or additives. Various alkyl carboxylic acids and amino acid derivatives are used as alkylating reagents to synthesize the gamma,delta-unsaturated diesters, and unnatural homo-allylic amino acid derivatives with excellent functional groups tolerance. The utility of this method was showcased by performing a gram-scale synthesis. A mechanism is proposed based on control experiments and quenching studies.

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