Palladium-Catalyzed Three-Component Coupling Reaction of Benzyl Chlorides, Allyltributylstannane, and Carbon Monoxide: Efficient Synthesis of α,β-Unsaturated Ketones

doi:10.3724/SP.J.1088.2011.10930

Abstract

Abstract: Palladium-catalyzed three-component coupling reactions of benzyl chlorides, allyltributylstannane, and carbon monoxide were investigated. These three-component coupling reactions proceeded smoothly in the presence of Pd(PPh₃)₄ to give benzyl allyl ketone products, which could transform to α,β-unsaturated ketone compounds 6a–6n after purification via basic alumina column chromatography. α,β-Unsaturated ketone compounds 6b, 6d–h, 6j, 5l, and 6l–6n are unknown compounds, and their structure was characterized by infrared spectroscopy, ¹H nuclear magnetic resonance spectroscopy, ¹³C nuclear magnetic resonance spectroscopy, and high-resolution mass spectroscopy.

Key words: benzyl chloride, carbon monoxide, allyltributylstannane, coupling, α,β-unsaturated ketone

ZHANG Xin, FENG Xiu-Juan, LIU He-Song, QIN Yu-Hu, DAI Yao. Palladium-Catalyzed Three-Component Coupling Reaction of Benzyl Chlorides, Allyltributylstannane, and Carbon Monoxide: Efficient Synthesis of α,β-Unsaturated Ketones[J]. Chinese Journal of Catalysis, 2012, 33(3): 523-529.

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URL: https://www.cjcatal.com/EN/10.3724/SP.J.1088.2011.10930

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