SIOC English
有机化学
高级检索

有机化学 >

2020 , Vol. 40 >Issue 2: 384 - 390

DOI: https://doi.org/10.6023/cjoc201909041

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
展开
  • 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

  网络出版日期: 2019-11-01

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.

收起

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

  • Li Qingxue ,
  • Li Mengwei ,
  • Shi Shaoqing ,
  • Ji Xiaoshuang ,
  • He Chunlan ,
  • Jiang Bo ,
  • Hao Wenjuan
Expand
  • School of Chemistry&Materials Science, Jiangsu Normal University, Xuzhou 221116

Received date: 2019-09-30

  Revised date: 2019-10-15

  Online 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).

Fold

摘要

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

本文引用格式

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 . DOI: 10.6023/cjoc201909041

Abstract

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

参考文献

[1] (a) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley-Inter-science, New York, 1998.
(b) Zhao, X.; Zhang, Y.; Wang, J. Chem. Commun. 2012, 48, 10162.
(c) Zhu, S.-F.; Zhou, Q.-L. Nat. Sci. Rev. 2014, 1, 580.
(d) Gillingham, D.; Fei, N. Chem. Soc. Rev. 2013, 42, 4918.
(e) Ford, A.; Miel, H.; Ring, A.; Slattery, C. N.; Maguire, A. R.; Mckervey, M. A. Chem. Rev. 2015, 115, 9981.
(f) Zhang, Z.; Wang, J. Chem. Commun. 2009, 64, 5350.
(g) Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704.
(h) Zhu, S.-F.; Zhou, Q.-L. Acc. Chem. Res. 2012, 45, 1365.
(i) Candeias, N.; Paterna, R.; Gois, P. M. P. Chem. Rev. 2016, 116, 2937.
(j) Zhang, T.-S.; Zhao, Q.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Chem. Asian. J. 2019, 14, 1042.
(k) Zhang, D.; Hu, W. H. Chem. Rec. 2017, 17, 739.
(l) Qiu, D.; Qiu, M.; Ma, R.; Zhang, Y.; Wang, J. Acta Chim. Sinica 2016, 74, 472(in Chinese). (邱頔, 邱孟龙, 马戎, 张艳, 王剑波, 化学学报, 2016, 74, 472.)
[2] (a) Liu, L.; Zhang, J. Chin. J. Org. Chem. 2017, 37, 1117(in Chinese). (刘路, 张俊良, 有机化学, 2017, 37, 1117.)
(b) Wu, Y.-N.; Xu, T.; Fu, R.; Wang, N.-N.; Hao, W.-J.; Wang, S.-L.; Li, G.; Tu, S.-J.; Jiang, B. Chem. Commun. 2016, 52, 11943.
[3] (a) Clapham, B.; Spanka, C.; Janda, K. D. Org. Lett. 2001, 3, 2173.
(b) Matsushita, H.; Lee, S.-H.; Yoshida, K.; Clapham, B.; Koch, G.; Zimmermann, J.; Janda, K. D. Org. Lett. 2004, 6, 4627.
[4] (a) Tan, F.; Liu, X.; Hao, X.; Tang, Y.; Lin, L.; Feng, X. ACS Catal. 2016, 6, 6930.
(b) Zhang, Y.; Yao, Y.; He, L.; Liu, Y.; Shi, L. Adv. Synth. Catal. 2017, 359, 2754.
(c) Feng, J.; Yi, X.; Fu, Y.; Yu, Y.; Huang, F. Chin. J. Org. Chem. 2019, 39, 3013(in Chinese). (封佳俊, 易享炎, 傅耀锋, 于杨, 黄菲, 有机化学, 2019, 39, 3013.)
[5] (a) Maas, G. Chem. Soc. Rev. 2004, 33, 183.
(b) Sambasivanand, R.; Ball, Z. T. Angew. Chem., Int. Ed. 2012, 51, 8568.
(c) Adly, F. G.; Gardiner, M. G.; Ghanem, A. Chem.-Eur. J. 2016, 22, 3447.
(d) Qin, C.; Boyarskikh, V.; Hansen, J. H.; Hardcastle, K. I.; Musaev, D. G.; Davies, H. M. L. J. Am. Chem. Soc. 2011, 133, 19198.
(e) Xu, H.; Li, Y.-P.; Cai, Y.; Wang, G.-P.; Zhu, S. F.; Zhou, Q.-L. J. Am. Chem. Soc. 2017, 139, 7697.
[6] (a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
(b) Yakura, T.; Ozono, A.; Matsui, K.; Yamashita, M.; Fujiwara, T. Synlett 2013, 24, 65.
(c) Roberts, E.; Sançon, J. P.; Sweeney, J. B. Org. Lett. 2005, 7, 2075.
[7] (a) Neupane, P.; Li, X.; Jung, J. H.; Lee, Y. R.; Kim, S. H. Tetrahedron 2012, 68, 2496.
(b) Dyer, J.; Jockusch, S.; Balsanek, V.; Sames, D.; Turro, N. J. Org. Chem. 2005, 70, 2143.
(c) Dussault, P. H.; Xu, C. Tetrahedron Lett. 2004, 45, 7455.
[8] (a) Wang, N.-N.; Huang, L.-R.; Hao, W.-J.; Zhang, T.-S.; Li, G.; Tu, S.-J.; Jiang, B. Org. Lett. 2016, 18, 1298.
(b) Hao, W.-J.; Gao, Q.; Jiang, B.; Liu, F.; Wang, S.-L.; Tu, S.-J.; Li, G. J. Org. Chem. 2016, 81, 11276.
(c) Wang, N.-N.; Hao, W.-J.; Zhang, T.-S.; Li, G.; Wu, Y.-N.; Tu, S.-J.; Jiang, B. Chem. Commun. 2016, 52, 5144.
(d) Zhang, T.-S.; Hao, W.-J.; Wang, N.-N.; Li, G.; Jiang, D.-F.; Tu, S.-J.; Jiang, B. Org. Lett. 2016, 18, 3078.
(e) Zhang, T.-S.; Zhang, H.; Fu, R.; Wang, J.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Chem. Commun. 2019, 55, 13231.
[9] (a) Jiang, B.; Li, J.; Pan, Y.-Y.; Hao, W.-J.; Li, G.; Tu, S.-J. Chin. J. Chem. 2017, 35, 323.
(b) Qiu, J.-K.; Jiang, B.; Zhu, Y.-L.; Hao, W.-J.; Wang, D.-C.; Sun, J.; Wei, P.; Tu S.-J.; Li, G. J. Am. Chem. Soc. 2015, 137, 8928.
(c) Huang, M.-H.; Hao, W.-J.; Li, G.; Tu, S.-J.; Jiang, B. Chem. Commun. 2018, 54, 10791.
(d) Huang, M.-H.; Hao, W.-J.; Jiang, B. Chem. Asian J. 2018, 13, 2958
(e) Peng, H. H.; Yuan, Z. L.; Chen, P. H.; Liu, G. S. Chin. J. Chem. 2017, 35, 876.
(f) Song, H.; Liu, X. Y.; Qin, Y. Acta Chim. Sinica 2017, 75, 1137(in Chinese). (宋颢, 刘小宇, 秦勇, 化学学报, 2017, 75, 1137.)
(g) Wei, W.; Wang, L.; Bao, P.; Shao, Y.; Yue, H.; Yang, D.; Yang, X.; Zhao, X.; Wang H. Org. Lett. 2018, 20, 7125.
(i) Wang, L.; Bao, P.; Liu, W.; Liu, S.; Hu, C.; Yue, H.; Yang, D.; Wei, W. Chin. J. Org. Chem. 2018, 38, 3189(in Chinese). (王雷雷, 鲍鹏丽, 刘维伟, 刘思彤, 胡昌松, 岳会兰, 杨道山, 魏伟, 有机化学, 2018, 38, 3189.)
[10] (a) Lu, F.-D.; Jiang, X.; Lu, L.-Q.; Xiao, W.-J. Acta Chim. Sinica 2019, 77, 803(in Chinese). (路福东, 姜烜, 陆良秋, 肖文精, 化学学报, 2019, 77, 803.)
(b) Hai, M.; Guo, L.-N.; Wang, L.; Duan, X.-H. Acta Chim. Sinica 2019, 77, 895(in Chinese). (海曼, 郭丽娜, 王乐, 段新华, 化学学报, 2019, 77, 895.)
(c) Yang, J.; Fu, X.; Lu, Z.; Zhu, G. Acta Chim. Sinica 2019, 77, 901(in Chinese). (杨俊航, 傅晓波, 卢增辉, 朱钢国, 化学学报, 2019, 77, 901.)
(d) Lin, F.; Liang, Y.; Li, X.; Song, S.; Jiao, N. Acta Chim. Sinica 2019, 77, 906(in Chinese). (林凤闺蓉, 梁宇杰, 郦鑫耀, 宋颂, 焦宁, 化学学报, 2019, 77, 906.)
(e) Tang, N.; Shao, X.; Wang, M.; Wu, X.; Zhu, C. Acta Chim. Sinica 2019, 77, 922(in Chinese). (汤娜娜, 邵鑫, 王明扬, 吴新鑫, 朱晨, 化学学报, 2019, 77, 922.)
(f) Zhao, Q.; Tu, S.-J.; Jiang B. Acta Chim. Sinica 2019, 77, 927(in Chinese). (赵琦, 屠树江, 姜波, 化学学报, 2019, 77, 927.)
(g) Fu, R.; Li, M.-F.; Zhou, P.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Adv. Synth. Catal. 2019, 361, 2280.
[11] (a) Lu, H.; Dzik, W. I.; Xu, X.; Wojtas, L.; de Bruin, B.; Zhang, X. P. J. Am. Chem. Soc. 2011, 133, 8518.
(b) Zheng, J.; Qi, J.; Cui, S. J. Org. Chem. 2015, 80, 9224.
(c) Jiang, J.; Liu, J.; Yang, L.; Shao, Y.; Cheng, J.; Bao, X.; Wan, X. Chem. Commun. 2015, 51, 14728.
[12] Zhang, J.; Jiang, J.; Xu, D.; Luo, Q.; Wang, H.; Chen, J.; Li, H.; Wang, Y.; Wan, X. Angew. Chem., Int. Ed. 2015, 54, 1231.
[13] Wang, N.-N.; Hao, W.-J.; Zhang, T.-S.; Li, G.; Wu, Y.-N.; Tu, S.-J.; Jiang, B. Chem. Commun. 2016, 52, 5144.
[14] (a) Lu, Y.; Han, Y.; Sun, Y.; Abdukader, A.; Wang, D.; Liu, C. Chin. J. Org. Chem. 2020, 40, 447(in Chinese). (陆雨函, 韩颖芝, 孙亚栋, 阿布力米提·阿布都卡德尔, 王多志, 刘晨江, 有机化学, 2020, 40, 447.)
(b) Chen, Q.; Yang, Y.; Wang, X.; Zhang, Q.; Li, D. Chin. J. Org. Chem. 2020, 40, 454(in Chinese). (陈倩雯, 杨耀成, 王霞, 张谦, 李栋, 有机化学, 2020, 40, 454.)
Options
文章导航

/

〈 〉