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Irradiation-induced palladium-catalyzed decarboxylative desaturation enabled by a dual ligand system

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  • Wan-Min Cheng

    (University of Science and Technology of China)

  • Rui Shang

    (University of Science and Technology of China)

  • Yao Fu

    (University of Science and Technology of China)

Abstract

Generation of alkenes through decarboxyolefination of alkane carboxylates has significant synthetic value in view of the easy availability of a variety of carboxylic acids and the synthetic versatility of alkenes. Herein we report that palladium catalysts under irradiation with blue LEDs (440 nm) catalyze decarboxylative desaturation of a variety of aliphatic carboxylates to generate aliphatic alkenes, styrenes, enol ethers, enamides, and peptide enamides under mild conditions. The selection of a dual phosphine ligand system is the key enabler for the successful development of this reaction. The Pd-catalyzed decarboxylative desaturation is utilized to achieve a three-step divergent synthesis of Chondriamide A and Chondriamide C in overall 68% yield from simple starting materials. Mechanistic studies suggest that, distinct from palladium catalysis under thermal condition, irradiation-induced palladium catalysis involves irradiation-induced single-electron transfer and dynamic ligand-dissociation/association process to allow two phosphine ligand to work synergistically.

Suggested Citation

  • Wan-Min Cheng & Rui Shang & Yao Fu, 2018. "Irradiation-induced palladium-catalyzed decarboxylative desaturation enabled by a dual ligand system," Nature Communications, Nature, vol. 9(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-07694-w
    DOI: 10.1038/s41467-018-07694-w
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