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

Wan-Min Cheng, Rui Shang () and Yao Fu ()
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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

Nature Communications, 2018, vol. 9, issue 1, 1-9

Abstract: 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.

Date: 2018
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DOI: 10.1038/s41467-018-07694-w

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