Citation: Zhou Hao, Chen Zhiyuan. Recent Achievements in the Synthesis of Sulfoximine Derivatives[J]. Chinese Journal of Organic Chemistry, ;2018, 38(4): 719-737. doi: 10.6023/cjoc201710002 shu

Recent Achievements in the Synthesis of Sulfoximine Derivatives

Zhou Hao ,
Chen Zhiyuan ^,

Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022

Corresponding author: Chen Zhiyuan, zchen@jxnu.edu.cn
Received Date: 6 October 2017
Revised Date: 29 November 2017
Available Online: 15 April 2017
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21462022, 21672085)Project supported by the National Natural Science Foundation of China 21672085Project supported by the National Natural Science Foundation of China 21462022

Figures(30)

The sulfoximine derivatives are widely known for their potent biological and medicinal activities. Recently, due to the transition-metal catalysis, great advancements have been achieved in the synthesis of sulfoximine derivatives. Utilizing free NH-sulfoximines as the starting materials, various the direct N-H functionalizations can be accomplished, such as alkynylation, alkenylation, alkylation, arylation, etc. In addition, the ortho arene C(sp²)-H activation can also be obtained through C-H activation reaction with the assistance of S=NH as intramolecular directing groups, thus giving varies (hetero)aromatic molecules. N-H and C-H functionalization reactions of sulfoximines were summarized, and the mechanisms of some novel model reactions are also briefly discussed.
- NH-sulfoximine,
- transition-metal-catalysis,
- C-H functionalization
1. [1]
  Bentley, H. R.; McDermott, E. E.; Pace, J.; Whitehead, J. K.; Moran, T. Nature 1950, 165, 150. doi: 10.1038/165150a0
2. [2]
  (a) Langner, M. ; Bolm, C. Angew. Chem. , Int. Ed. 2004, 43, 5984.
  (b) Shen, X. ; Zhang, W. ; Ni, C. ; Gu, Y. ; Hu, J. J. Am. Chem. Soc. 2012, 134, 16999.
  (c) Harmata, M. ; Hong, X. J. Am. Chem. Soc. 2003, 125, 5754.
  (d) Koep, S. ; Gais, H. -J. ; Raabe, G. J. Am. Chem. Soc. 2003, 125, 13243.
  (e) Moessner, C. ; Bolm, C. Angew. Chem. , Int. Ed. 2005, 44, 7564.
3. [3]
  Miller, P.; James, G. W. L. Arch. Int. Pharmacodyn. Ther. 1978, 231, 328.
4. [4]
  Park, S. J.; Baars, H.; Mersmann, S.; Buschmann, H.; Baron, J. M.; Amann, P. M.; Czaja, K.; Hollert, H.; Bluhm, K.; Redelstein, R.; Bolm, C. ChemMedChem 2013, 8, 217. doi: 10.1002/cmdc.201200403
5. [5]
  Lucking, U.; Jautelat, R.; Kruger, M.; Brumby, T.; Lienau, P.; Schafer, M.; Briem, H.; Schulze, J.; Hillisch, A.; Reichel, A.; Siemeister, G. ChemMedChem 2013, 8, 1021. doi: 10.1002/cmdc.201390025
6. [6]
  Satzinger, G. Drug News Perspect. 2001, 14, 197. doi: 10.1358/dnp.2001.14.4.858403
7. [7]
  Von Nussbaum, F.; Karthaus, D.; Anlauf, S.; Delbeck, M.; Li, V.; Meibom, D.; Lustig, K.; Schneider, D. WO 2010115548, 2010.
8. [8]
  Walker, D.; Zawistoski, M.; McGlynn, M.; Li, J.; Kung, D. W.; Bonnette, P.; Baumann, A.; Buckbinder, L.; Houser, J. A.; Boer, J.; Mistry, A.; Han, S.; Xing, L.; Perez, A. B. Bioorg. Med. Chem. Lett. 2009, 19, 3253. doi: 10.1016/j.bmcl.2009.04.093
9. [9]
  Ulrich, L. Angew. Chem., Int. Ed. 2013, 52, 9399. doi: 10.1002/anie.v52.36
10. [10]
  (a) Bentley, H. R. ; Whitehead, J. K. J. Chem. Soc. 1952, 1572.
  (b) Johnson, C. R. ; Haake, M. ; Schroeck, C. W. J. Am. Chem. Soc. 1970, 92, 6594.
  (c) Stoss, P. ; Satzinger, G. Angew. Chem. , Int. Ed. 1971, 10, 76.
  (d) Johnson, C. R. ; Schroeck, C. W. J. Am. Chem. Soc. 1973, 95, 7418.
  (e) Rynbrandt, R. H. ; Balgoyen, D. P. J. Org. Chem. 1978, 43, 1824.
  (f) Brandt, J. ; Gais, H. J. Tetrahedron: Asymmetry 1997, 8, 909.
11. [11]
  (a) Tamura, Y. ; Sumoto, K. ; Minamikawa, J. ; Ikeda, M. Tetrahedron Lett. 1972, 4137.
  (b) Tamura, Y. ; Minamikawa, J. ; Sumoto, K. ; Fujii, S. ; Ikeda, M. J. Org. Chem. 1973, 38, 1239.
  (c) Johnson, C. R. ; Kirchhoff, R. A. ; Corkins, H. G. J. Org. Chem. 1974, 39, 2458.
  (d) Allenmark, S. ; Claeson, S. ; Lowendahl, C. Tetrahedron: Asymmetry 1996, 7, 361.
12. [12]
  (a) Takada, H. ; Ohe, K. ; Uemura, S. Angew. Chem. , Int. Ed. 1999, 38, 1288.
  (b) Lacote, E. ; Amatore, M. ; Fensterbank, L. ; Malacria, M. Synlett 2002, 116.
  (c) Cren, S. ; Kinahan, T. C. ; Skinner, C. L. ; Tye, H. Tetrahedron Lett. 2002, 43, 2749.
  (d) Okamura, H. ; Bolm, C. Org. Lett. 2004, 6, 1305.
  (e) Cho, G. Y. ; Bolm, C. Org. Lett. 2005, 7, 4983.
  (f) Mancheno, O. G. ; Bolm, C. Org. Lett. 2006, 8, 2349.
  (g) Mancheno, O. G. ; Dallimore, J. ; Plant, A. ; Bolm, C. Org. Lett. 2009, 11, 2429.
13. [13]
  Miao, J.; Richards, N. G. J.; Ge, H. Chem. Commun. 2014, 50, 9687. doi: 10.1039/C4CC04349A
14. [14]
  Zenzola, M.; Doran, R.; Degennaro, L.; Luisi, R.; Bull, J. A. Angew. Chem., Int. Ed. 2016, 55, 7203. doi: 10.1002/anie.201602320
15. [15]
  Wang, J.; Frings, M.; Bolm, C. Chem.-Eur. J. 2014, 20, 966. doi: 10.1002/chem.201303850
16. [16]
  Cheng, Y.; Dong, W.; Wang, L.; Parthasarathy, K.; Bolm, C. Org. Lett. 2014, 16, 2000. doi: 10.1021/ol500573f
17. [17]
  Teng, F.; Cheng, J.; Yu, J.-T. Org. Biomol. Chem. 2015, 13, 9934. doi: 10.1039/C5OB01558H
18. [18]
  Teng, F.; Sun, S.; Jiang, Y.; Yu, J.-T.; Cheng, J. Chem. Commun. 2015, 51, 5902. doi: 10.1039/C5CC00839E
19. [19]
  Teng, F.; Cheng, J.; Bolm, C. Org. Lett. 2015, 17, 3166. doi: 10.1021/acs.orglett.5b01537
20. [20]
  Wang, H.; Frings, M.; Bolm, C. Org. Lett. 2016, 18, 2431. doi: 10.1021/acs.orglett.6b00958
21. [21]
  Dehli, J. R.; Bolm, C. J. Org. Chem. 2004, 69, 8518. doi: 10.1021/jo0485583
22. [22]
  Chen, X.-Y.; Bohmann, R. A.; Wang, L.; Dong, S.; R uber, C.; Bolm, C. Chem.-Eur. J. 2015, 21, 10330. doi: 10.1002/chem.201501629
23. [23]
  Chen, Z.; Huang, J.; Wang, Z. J. Org. Chem. 2016, 81, 9308. doi: 10.1021/acs.joc.6b01891
24. [24]
  Wang, L.; Huang, H.; Priebbenow, D. L.; Pan, F.-F.; Bolm, C. Angew. Chem., Int. Ed. 2013, 52, 3478. doi: 10.1002/anie.v52.12
25. [25]
  Priebbenow, D. L.; Becker, P.; Bolm, C. Org. Lett. 2013, 15, 6155. doi: 10.1021/ol403106e
26. [26]
  Chen, X. Y.; Wang, L.; Frings, M.; Bolm, C. Org. Lett. 2014, 16, 3796. doi: 10.1021/ol5016898
27. [27]
  Wang, H.; Cheng, Y.; Becker, P.; Raabe, G.; Bolm, C. Angew. Chem., Int. Ed. 2016, 55, 12655. doi: 10.1002/anie.201605743
28. [28]
  Pirwerdjan, R.; Priebbenow, D. L.; Becker, P.; Lamers, P.; Bolm, C. Org. Lett. 2013, 15, 5397. doi: 10.1021/ol4026028
29. [29]
  Pirwerdjan, R.; Becker, P.; Bolm, C. Org. Lett. 2015, 17, 5008. doi: 10.1021/acs.orglett.5b02477
30. [30]
  Pirwerdjan, R.; Becker, P.; Bolm, C. Org. Lett. 2016, 18, 3307. doi: 10.1021/acs.orglett.6b01646
31. [31]
  Bolm, C.; Hildebrand, J. P. J. Org. Chem. 2000, 65, 169. doi: 10.1021/jo991342u
32. [32]
  Cho, G. Y.; Rémy, P.; Jansson, J.; Moessner, C.; Bolm, C. Org. Lett. 2004, 6, 3293. doi: 10.1021/ol048806h
33. [33]
  Sedelmeier, J.; Bolm, C. J. Org. Chem. 2005, 70, 6904. doi: 10.1021/jo051066l
34. [34]
  Moessner, C.; Bolm, C. Org. Lett. 2005, 7, 2667. doi: 10.1021/ol050816a
35. [35]
  Kim, J.; Ok, J.; Kim, S.; Choi, W.; Lee, P. H. Org. Lett. 2014, 16, 4602. doi: 10.1021/ol502174n
36. [36]
  Miyasaka, M.; Hirano, K.; Satoh, T.; Kowalczyk, R.; Bolm, C.; Miura, M. Org. Lett. 2010, 13, 359.
37. [37]
  Wang, L.; Priebbenow, D. L.; Dong, W.; Bolm, C. Org. Lett. 2014, 16, 2661. doi: 10.1021/ol500963p
38. [38]
  Aithagani, S. K.; Kumar, M.; Yadav, M.; Vishwakarma, R. A.; Singh, P. P. J. Org. Chem. 2016, 81, 5886. doi: 10.1021/acs.joc.6b00593
39. [39]
  Aithagani, S. K.; Dara, S.; Munagala, G.; Aruri, H.; Yadav, M.; Singh, P. P. Org. Lett. 2015, 17, 5547. doi: 10.1021/acs.orglett.5b02804
40. [40]
  Priebbenow, D. L.; Bolm, C. Org. Lett. 2014, 16, 1650. doi: 10.1021/ol5003016
41. [41]
  Zou, Y.; Xiao, J.; Peng, Z.; Dong, W.; An, D. Chem. Commun. 2015, 51, 14889. doi: 10.1039/C5CC05483D
42. [42]
  Qin, W. J.; Li, Y.; Yu, X.; Deng, W.-P. Tetrahedron 2015, 71, 1182. doi: 10.1016/j.tet.2015.01.013
43. [43]
  Dong, S.; Frings, M.; Cheng, H.; Wen, J.; Zhang, D.; Raabe, G.; Bolm, C. J. Am. Chem. Soc. 2016, 138, 2166. doi: 10.1021/jacs.6b00143
44. [44]
  Zhou, H.; Hong, J.; Huang, J.-P.; Chen, Z.-Y. Asian J. Org. Chem. 2017, 6, 817. doi: 10.1002/ajoc.v6.7
45. [45]
  Teng, F.; Yu, J. T.; Jiang, Y.; Yang, H.; Cheng, J. Chem. Commun. 2014, 50, 8412. doi: 10.1039/c4cc03439b
46. [46]
  Hu, W.; Teng, F.; Peng, H.; Yu, J.; Sun, S.; Cheng, J. Shao, Y. Tetrahedron Lett. 2015, 56, 7056. doi: 10.1016/j.tetlet.2015.11.025
47. [47]
  Teng, F.; Yu, J.-T.; Zhou, Z.; Chu, H.; Cheng, J. J. Org. Chem. 2015, 80, 2822. doi: 10.1021/jo502607c
48. [48]
  Dannenberg, C. A.; Fritze, L.; Krauskopf, F.; Bolm, C. Org. Biomol. Chem. 2017, 15, 1086. doi: 10.1039/C6OB02691E
49. [49]
  Peng, H.; Yu, J. T.; Bao, W.; Xu, J.; Cheng, J. Org. Biomol. Chem. 2015, 13, 10600. doi: 10.1039/C5OB01705J
50. [50]
  Bohnen, C.; Bolm, C. Org. Lett. 2015, 17, 3011. doi: 10.1021/acs.orglett.5b01384
51. [51]
  Zhu, H.; Yu, J.-T.; Cheng, J. Chem. Commun. 2016, 52, 11908. doi: 10.1039/C6CC06359D
52. [52]
  Yadav, M. R.; Rit, R. K.; Sahoo, A. K. Chem.-Eur. J. 2012, 18, 5541. doi: 10.1002/chem.v18.18
53. [53]
  Rit, R. K.; Yadav, M. R.; Sahoo, A. K. Org. Lett. 2012, 14, 3724. doi: 10.1021/ol301579q
54. [54]
  Rit, R. K.; Yadav, M. R.; Ghosh, K.; Shankar, M.; Sahoo, A. K. Org. Lett. 2014, 16, 5258. doi: 10.1021/ol502337b
55. [55]
  Yadav, M. R.; Rit, R. K.; Sahoo, A. K. Org. Lett. 2013, 15, 1638. doi: 10.1021/ol400411v
56. [56]
  Yadav, M. R.; Rit, R. K.; Shankar, M.; Sahoo, A. K. J. Org. Chem. 2014, 79, 6123. doi: 10.1021/jo5008465
57. [57]
  Yadav, M. R.; Shankar, M.; Ramesh, E.; Ghosh, K.; Sahoo, A. K. Org. Lett. 2015, 17, 1886. doi: 10.1021/acs.orglett.5b00570
58. [58]
  Raghuvanshi, K.; Zell, D.; Ackermann, L. Org. Lett. 2017, 19, 1278. doi: 10.1021/acs.orglett.6b03898
59. [59]
  Shankar, M.; Ghosh, K.; Mukherjee, K.; Rit, R. K.; Sahoo, A. K. Org. Lett. 2016, 18, 6416. doi: 10.1021/acs.orglett.6b03314
60. [60]
  Chinnagolla, R. K.; Vijeta, A.; Jeganmohan, M. Chem. Commun. 2015, 51, 12992. doi: 10.1039/C5CC04589D
61. [61]
  Huang, J.; Huang, Y.; Wang, T.; Huang, Q.; Wang, Z.; Chen, Z.-Y. Org. Lett. 2017, 19, 1128. doi: 10.1021/acs.orglett.7b00120
62. [62]
  Parthasarathy, K.; Bolm, C. Chem.-Eur. J. 2014, 20, 4896. doi: 10.1002/chem.201304925
63. [63]
  Dong, W.; Parthasarathy, K.; Cheng, Y.; Pan, F.; Bolm, C. Chem.-Eur. J. 2014, 20, 15732. doi: 10.1002/chem.v20.48
64. [64]
  Cheng, Y.; Dong, W.; Wang, H.; Bolm, C. Chem.-Eur. J. 2016, 22, 10821. doi: 10.1002/chem.201602550
65. [65]
  Dong, W.; Wang, L.; Parthasarathy, K.; Pan, F.; Bolm, C. Angew. Chem., Int. Ed. 2013, 52, 11573. doi: 10.1002/anie.201304456
66. [66]
  Cheng, Y.; Bolm, C. Angew. Chem., Int. Ed. 2015, 127, 12526. doi: 10.1002/ange.201501583
67. [67]
  Jeon, W. H.; Son, J. Y.; Kim, J. E.; Lee, P. H. Org. Lett. 2016, 18, 3498. doi: 10.1021/acs.orglett.6b01750
68. [68]
  Wen, J.; Tiwari, D. P.; Bolm, C. Org. Lett. 2017, 19, 1706. doi: 10.1021/acs.orglett.7b00488
1. [1]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
2. [2]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
3. [3]
  Yan Qi , Yueqin Yu , Weisi Guo , Yongjun Liu . 过渡金属参与的有机反应案例教学与实践探索. University Chemistry, 2025, 40(6): 111-117. doi: 10.12461/PKU.DXHX202411021
4. [4]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
5. [5]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
6. [6]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
7. [7]
  Fugui XI , Du LI , Zhourui YAN , Hui WANG , Junyu XIANG , Zhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291
8. [8]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
9. [9]
  Wei-Bin Li , Xiao-Chao Huang , Pei Liu , Jie Kong , Guo-Ping Yang . Recent advances in directing group assisted transition metal catalyzed para-selective C-H functionalization. Chinese Chemical Letters, 2025, 36(6): 110543-. doi: 10.1016/j.cclet.2024.110543
10. [10]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
11. [11]
  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
12. [12]
  Fei Xie , Chengcheng Yuan , Haiyan Tan , Alireza Z. Moshfegh , Bicheng Zhu , Jiaguo Yu . d带中心调控过渡金属单原子负载COF吸附O₂的理论计算研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2407013-. doi: 10.3866/PKU.WHXB202407013
13. [13]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
14. [14]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-. doi: 10.3866/PKU.WHXB202407005
15. [15]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
16. [16]
  Guangming YIN , Huaiyao WANG , Jianhua ZHENG , Xinyue DONG , Jian LI , Yi'nan SUN , Yiming GAO , Bingbing WANG . Preparation and photocatalytic degradation performance of Ag/protonated g-C₃N₄ nanorod materials. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1491-1500. doi: 10.11862/CJIC.20240086
17. [17]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
18. [18]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
19. [19]
  Tong Zhou , Xue Liu , Liang Zhao , Mingtao Qiao , Wanying Lei . Efficient Photocatalytic H₂O₂ Production and Cr(VI) Reduction over a Hierarchical Ti₃C₂/In₄SnS₈ Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-. doi: 10.3866/PKU.WHXB202309020
20. [20]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317

Get Citation

PDF

XML

Metrics

PDF Downloads(43)
Abstract views(2436)
HTML views(692)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142