醋酸碘苯介导的α-重氮羰基化合物的去重氮双氧合反应

doi:10.6023/cjoc201909041

有机化学 ›› 2020, Vol. 40 ›› Issue (2): 384-390.DOI: 10.6023/cjoc201909041 上一篇下一篇

研究论文

醋酸碘苯介导的α-重氮羰基化合物的去重氮双氧合反应

李庆雪, 李梦伟, 时绍青, 季晓霜, 何春兰, 姜波, 郝文娟

江苏师范大学化学与材料科学学院徐州 221116

收稿日期:2019-09-30 修回日期:2019-10-15 发布日期:2019-11-01
通讯作者: 姜波, 郝文娟 E-mail:jiangchem@jsnu.edu.cn;wjhao@jsnu.edu.cn
基金资助:
国家自然科学基金（No.21602087）、江苏省品牌专业基金和国家级大学生创新创业训练计划（Nos.201810320156X，201810320019Z）资助项目.

PhI(OAc)₂-Mediated Dediazodioxygenation of α-Diazo Carbonyls

Li Qingxue, Li Mengwei, Shi Shaoqing, Ji Xiaoshuang, He Chunlan, Jiang Bo, Hao Wenjuan

School of Chemistry&Materials Science, Jiangsu Normal University, Xuzhou 221116

Received:2019-09-30 Revised:2019-10-15 Published:2019-11-01
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21602087), the Top-Notch Academic Programs Project of Jiangsu Higher Education Institutions and the National College Student's Innovation and Entrepreneurship Training Program (Nos. 201810320156X, 201810320019Z).

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摘要/Abstract

报道了一类新颖的醋酸碘苯介导的α-重氮羰基化合物的去重氮双氧合反应.该反应利用醋酸碘苯与N-羟基邻苯二甲酰亚胺（或N-羟基丁二甲酰亚胺）反应能产生氧中心自由基的特性实现了氧中心自由基诱导的α-重氮羰基化合物的双氧合反应，合成了一系列α，α-双氧代芳酮和α，α-双氧代羧酸酯衍生物，产率中等到良好.基于实验结果及文献报道，提出了可能的反应机理，其涉及氧中心自由基加成、C-N键的均裂和自由基交叉偶联等.此外，该反应具有无需金属催化剂、条件温和、操作简便等优点.

关键词: 双氧合反应, 去重氮化反应, α,α-双氧代芳酮, α,α-双氧代羧酸酯

A new PhI(OAc)₂-mediated dediazodioxygenation of α-diazo carbonyls was reported. By using the characteristics of the in-situ-generated O-centered radicals from the interaction of PhI(OAc)₂ and N-hydroxy phthalimide (or N-hydroxy succinimide), O-centered radical-triggered dioxygenation of α-diazo carbonyls was achieved in this transformation, which led to the synthesis of a series of α,α-dioxoarylketones and α,α-dioxoesters with moderate to good yields. Based on the experimental results and literature reports, the possible reaction mechanism was proposed, which involved O-centered radical addition, C-N bond homolysis and radical cross coupling. In addition, the reaction featured mild conditions and simple operation without any catalyst.

Key words: dioxygenation, dediazotization, α,α-dioxoarylketones, α,α-dioxoesters

引用此文

李庆雪, 李梦伟, 时绍青, 季晓霜, 何春兰, 姜波, 郝文娟. 醋酸碘苯介导的α-重氮羰基化合物的去重氮双氧合反应[J]. 有机化学, 2020, 40(2): 384-390.

Li Qingxue, Li Mengwei, Shi Shaoqing, Ji Xiaoshuang, He Chunlan, Jiang Bo, Hao Wenjuan. PhI(OAc)₂-Mediated Dediazodioxygenation of α-Diazo Carbonyls[J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 384-390.

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醋酸碘苯介导的α-重氮羰基化合物的去重氮双氧合反应

PhI(OAc)₂-Mediated Dediazodioxygenation of α-Diazo Carbonyls

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