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| 利用自由基引发的1,2-炔基迁移实现非活性烯烃的炔膦酰化 | |
| 引用本文： | 张萍,石浩楠,张天舒,蔡佩君,姜波,屠树江. 利用自由基引发的1,2-炔基迁移实现非活性烯烃的炔膦酰化[J]. 有机化学, 2020, 0(2): 423-431 |
| 作者姓名： | 张萍 石浩楠 张天舒 蔡佩君 姜波 屠树江 |
| 作者单位： | 中国矿业大学化工学院;江苏师范大学化学与材料科学学院;江苏省徐州医药高等职业学校 |
| 基金项目： | 中央高校基本科研专项资金基金(No.JH180263)资助项目. |
| 摘 要： | 研究了1,4-烯炔衍生物与二芳基膦氧化物在银介导下发生的炔酰化反应.该反应利用自由基引发的1,2-炔基迁移策略合成了一系列γ-酮膦氧化物,产率适中.该反应机理可能涉及膦中心自由基与乙烯基的加成、3-exo-dig环化和1,2-炔基迁移等连续的过程,一步形成了C-P、C-C键等化学键,实现了非活性烯烃的双官能化. |
| 关 键 词： | 1,4-烯炔衍生物 炔膦酰化反应 γ-酮膦氧化物 炔基迁移 自由基化学 |
Alkynylphosphonation of Unactivated Olefins via Radical-Triggered 1,2-Alkynyl Migration |
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| Zhang Ping,Shi Haonan,Zhang Tianshu,Cai Peijun,Jiang Bo,Tu Shujiang. Alkynylphosphonation of Unactivated Olefins via Radical-Triggered 1,2-Alkynyl Migration[J]. Chinese Journal of Organic Chemistry, 2020, 0(2): 423-431 | |
| Authors: | Zhang Ping Shi Haonan Zhang Tianshu Cai Peijun Jiang Bo Tu Shujiang |
| Affiliation: | (School of Chemical Engineering&Technology,China University of Mining and Technology,Xuzhou,Jiangsu 221116;School of Chemistry&Materials Science,Jiangsu Normal University,Xuzhou,Jiangsu 221116;Jiangsu Provincial Xuzhou Pharmaceutical Vocational College,Xuzhou,Jiangsu 221116) |
| Abstract: | A silver-mediated alkynylphosphonation of 1,4-enynes with diarylphosphine oxides has been developed, by which a wide range of γ-ketophosphine oxides with moderate to good yields were synthesized through radical 1,2-alkynyl migration. The transformation proceeded with sequential P-centered radical addition to vinyl unit, 3-exo-dig cyclization and 1,2-alkynyl migration, resulting in the bond-forming events including C-P and C-C bonds to realize difunctionalization of unactivated olefins. |
| Keywords: | 1,4-enynes alkynylphosphonation γ-ketophosphine oxides alkynyl migration radical chemistry |
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