Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 14, Pages 2340-2345Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202200227
Keywords
photoredox catalysis; decarboxylation; vinylcyclopropanes; alkylation; amino acids
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Funding
- IISER Kolkata
- SERB
- DST-SERB
- UGC, IISER K
- 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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