催化学报

催化学报 ›› 2012, Vol. 33 ›› Issue (3): 523-529.DOI: 10.3724/SP.J.1088.2011.10930

• 研究论文 • 上一篇    下一篇

钯催化苄基氯衍生物、三丁基烯丙基锡和一氧化碳三组分偶联反应: α,β-不饱和酮的有效合成

张新 1, 冯秀娟 2,a, 刘鹤松 3,b, 秦余虎 2, 戴耀 2   

  1. 1大连理工大学环境学院工业生态与环境工程教育部重点实验室, 辽宁大连 116024; 2大连理工大学精细化工国家重点实验室, 辽宁大连 116024; 3吉林大学第一医院皮肤性病科, 吉林长春 130021
  • 收稿日期:2011-09-16 修回日期:2011-10-19 出版日期:2012-03-15 发布日期:2015-07-27

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

ZHANG Xin1, FENG Xiujuan2,a, LIU Hesong3,b, QIN Yuhu2, DAI Yao2   

  1. 1Key Laboratory of Industrial Ecology and Environmental Engineering (MOE), School of Environmental Science and Technology, Dalian 116024, Liaoning, China; 2State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, Liaoning, China; 3Department of Dermatology and Venereology, The First Hospital of Jilin University, Changchun 130021, Jilin, China
  • Received:2011-09-16 Revised:2011-10-19 Online:2012-03-15 Published:2015-07-27

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摘要： 研究了苄基氯衍生物、CO 和三丁基烯丙基锡在零价钯催化剂 (Pd(PPh3)4) 存在下的反应, 结果表明, 可有效发生三组分偶联反应, 生成不饱和酮化合物. 再经碱性氧化铝柱提纯后, 转化为 α,β-不饱和酮化合物 6a~6n, 其中, 6b, 6d~6h, 6j, 5l 和 6l~6n 等未见文献报道, 其结构经红外光谱、1H 和 13C 核磁共振以及高分辨质谱表征确定.

关键词: 苄基氯衍生物, 一氧化碳, 三丁基烯丙基锡, 偶联, α,β-不饱和酮

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