Citation: Guan Baochuan, Xu Xiaoliang, Wang Hong, Li Xiaonian. Progress on the Decarboxylation Coupling Reaction Mediated by Visible Light[J]. Chinese Journal of Organic Chemistry, ;2016, 36(7): 1564-1571. doi: 10.6023/cjoc201601012 shu

Progress on the Decarboxylation Coupling Reaction Mediated by Visible Light

1.
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Corresponding author: Xu Xiaoliang, xuxiaoliang@zjut.edu.cn Wang Hong, chem_hong@163.com
Received Date: 11 January 2016
Revised Date: 17 February 2016

Fund Project: the Natural Science Foundation of Zhejiang Province No. LY15B020004

Figures(9)

Visible light mediated coupling reaction has obtained the widespread attention in recent years, and has been a most efficient method for building new C—C and C—X bonds. The development of visible light catalytic system also has provided a new means for decarboxylation reaction. Lots of studies on visible light catalytic decarboxylation reaction were published recently. In this paper, the visible light mediated decarboxylation reactions in recent years are briefly reviewed.
- visible light catalysis,
- decarboxylation,
- coupling reaction
1. [1]
  Weaver, J. D; Recio, A; Grenning, A. J; Tunge, J. A. Chem. Rev. 2011, 111, 1846.
2. [2]
  Baudoin, O. Angew. Chem., Int. Ed. 2007, 46, 1373;
3. [3]
  Li, Z.; Jiang, Y. Y; Yeagley, A. A.; Bour, J. P.; Liu, L.; Chruma, J. J.; Fu, Y. Chem. Eur. J. 2012, 18, 14527.
4. [4]
  Burger, E. C.; Tunge, J. A. J. Am. Chem. Soc. 2006, 128, 10002.
5. [5]
  Yeagley, A. A.; Chruma, J. J. Org. Lett. 2007, 9, 2879.
6. [6]
  Xie, J.; Jin, H.; Xu, P.; Zhu, C. Tetrahedron Lett. 2014, 55, 36.
7. [7]
  Chen, J.; Cen, J.; Xu, X. L.; Li, X. N. Catal. Sci. Technol. 2016, 6, 349.
8. [8]
  Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77.
9. [9]
  Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875.
10. [10]
  Pirnot, M. T.; Rankic, D. A.; Martin, D. B. C.; MacMillan, D. W. C. Science 2013, 339, 1593.
11. [11]
  McNally, A.; Prier, C. K.; MacMillan, D. W. C. Science 2011, 334, 1114.
12. [12]
  Shih, H. W.; Wal, M. N. V.; Grange, R. L.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 13600.
13. [13]
  Jeffrey, J.; Petronijevic, F. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 8404.
14. [14]
  Ischay, M. A.; Anzovino, M. E.; Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 12886.
15. [15]
  Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2009, 131, 14604.
16. [16]
  Lin, S.; Ischay, M. A.; Fry, C. G.; Yoon, T. P. J. Am. Chem. Soc. 2011, 133, 19350.
17. [17]
  Lu, Z.; Yoon, T. P. Angew. Chem., Int. Ed. 2012, 51, 10329.
18. [18]
  Blum, T. R.; Zhu, Y.; Nordeen, S. A.; Yoon, T. P. Angew. Chem., Int. Ed. 2014, 53, 11056.
19. [19]
  Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. J. Am. Chem. Soc. 2009, 131, 8756.
20. [20]
  Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102.
21. [21]
  Condie, A. G.; Gonzalez-Gomez, J. C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2010, 132, 1464.
22. [22]
  Freeman, D. B.; Furst, L.; Condie, A. G.; Stephenson, C. R. J. Org. Lett. 2012, 14, 94.
23. [23]
  Xuan, J.; Cheng, Y.; An, J.; Lu, L. Q.; Zhang, X. X.; Xiao, W. J. Chem. Commun. 2011, 47, 8337.
24. [24]
  Zou, Y. Q.; Guo, W.; Liu, F. L.; Lu, L. Q.; Chen, J. R.; Xiao, W. J. Green Chem. 2014, 16, 3787.
25. [25]
  Xuan, J.; Xia, X. D.; Zeng, T. T.; Feng, Z. J.; Chen, J. R.; Lu, L. Q.; Xiao, W. J. Angew. Chem., Int. Ed. 2014, 53, 5633.
26. [26]
  Xie J.; Xu P.; Li, H.; Xue, Q.; Jin, H.; Cheng, Y.; Zhu, C. Chem. Commun. 2013, 49, 5672.
27. [27]
  Xuan, J.; Zhang, Z. G.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 15632.
28. [28]
  Zuo, Z.-W.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 5257
29. [29]
  Lloyd-Jones, G. C.; Ball, L. T. Science 2014, 345, 381.
30. [30]
  Terrett, J. A.; Cuthbertson, J. D.; Shurtleff1, V. W.; MacMillan, D. W. C. Nature 2015, 524, 330.
31. [31]
  Hopkinson, M. N.; Sahoo, B.; Glorius, F. Adv. Synth. Catal. 2014, 356, 2794.
32. [32]
  Tellis, J. C. Primer, D. N.; Molander, G. A. Science 2014, 345, 433.
33. [33]
  Cai, S.Y.; Yang, K.; Wang, D. Z. Org. Lett. 2014, 16, 2606.
34. [34]
  Choi, S.; Chatterjee, T.; Choi, W. J.; You, Y.; Cho, D. E. J. ACS Catal. 2015, 5, 4796.
35. [35]
  Shu, X. Z.; Zhang, M.; He, Y.; Frei, H.; Toste, F. D. J. Am. Chem. Soc. 2014, 136, 5844.
36. [36]
  Anderson, A. J. M.; Koehi, J. K. J. Am. Chem. Soc. 1970, 92, 1651.
37. [37]
  Miller, J. A.; Nelson, J. A.; Byrne, M. P. J. Org. Chem. 1993, 58, 18.
38. [38]
  Samuel, C.; Simone, T.; Mueller, J.; Jerome, L. Angew. Chem., Int. Ed. 2007, 46, 2082.
39. [39]
  Burger, E. C.; Tunge. J. A. Chem. Commun. 2005, 2835.
40. [40]
  Zuo, Z.; Ahneman, D. T.; Chu, L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437.
41. [41]
  Oderinde, M. S.; Varela-Alvarez, A.; Aquila, B.; Robbins, D. W.; Johannes, J. W. J. Org. Chem. 2015, 80, 7642.
42. [42]
  Chu, L.; Lipshultz, J. M.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2015, 54, 7929.
43. [43]
  Cheng, W. M.; Shang, R.; Yu, H. Z.; Fu, Y. Chem. Eur. J. 2015, 21, 13191.
44. [44]
  Noble, A.; McCarver, S. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 624.
45. [45]
  Zou, Y. Q.; Duan, S. W.; Meng, X. G.; Hu, X. Q.; Gao, S.; Chen, J. R. Xiao, W. J. Tetrahedron 2012, 68, 6914.
46. [46]
  Tucker, J. W.; Narayanam, J. M. R.; Krabbe, S. W.; Stephenson, C. R. J. Org. Lett. 2010, 12, 368.
47. [47]
  Furst, L.; Matsuura, B. S.; Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. Org. Lett. 2010, 12, 3104.
48. [48]
  Furst, L.; Narayanam, J. M. R.; Stephenson, C. R. J. Angew. Chem., Int. Ed. 2011, 50, 9655.
49. [49]
  Ju, X.; Liang, Y.; Jia, P.; Li, W.; Yu, W. Org. Biomol. Chem. 2012, 10, 498.
50. [50]
  Maity, S.; Zheng, N. Angew. Chem., Int. Ed. 2012, 51, 9562.
51. [51]
  Chen, M.; Huang, Z. T.; Zheng, Q. Y. Chem. Commun. 2012, 48, 11686.
52. [52]
  Fu, W.; Xu, F.; Fu, Y.; Zhu, M.; Yu, J.; Xu, C.; Zou, D. J. Org. Chem. 2013, 78, 12202.
53. [53]
  Zhang, P.; Xiao, T.; Xiong, S.; Dong, X.; Zhou, L. Org. Lett. 2014, 16, 3294.
54. [54]
  Gu, L.; Jin, C.; Liu, J.; Zhang, H.; Yuan, M.; Li, G. Green Chem. 2016, 18, 1201.
55. [55]
  Noble, A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 11602
56. [56]
  Huang, H.; Jia, K.; Chen, Y. Angew. Chem., Int. Ed. 2015, 54, 1881.
57. [57]
  Rueping, M.; Koenigs, R. M.; Poscharny, K.; Fabry, D. C. Leonori, D.; Vila, C. Chem. Eur. J. 2012, 18, 5170.
58. [58]
  Adrian, T. A.; Matthew, N. H.; Basudev, S.; Frank, G. Chem. Sci. 2016, 7, 89.
59. [59]
  Kim, S.; Martin, J. R.; Toste, F. D. Chem. Sci. 2016, 7, 85.
60. [60]
  Yang, J.; Zhang, J.; Qi, L.; Hu, C.; Chen, Y. Chem. Commun. 2015, 51, 5275.
61. [61]
  Huang, H.; Zhang, G.; Chen, Y. Angew. Chem., Int. Ed. 2015, 54, 7872.
62. [62]
  Zhou, Q. Q.; Guo, W.; Ding, W.; Wu, X.; Chen, X.; Lu, L. Q.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 11196.
63. [63]
  Guo, W.; Lu, L. Q.; Wang, Y.; Wang, Y. N.; Chen, J. R.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 2265.
64. [64]
  Majek, M.; Wangelin, A. J. Angew. Chem., Int. Ed. 2015, 54, 2270.
65. [65]
  Vaillant, F. L.; Courant, T.; Waser, J. Angew. Chem., Int. Ed. 2015, 54, 11200.
66. [66]
  Tan, H.; Li, H.; Ji, W.; Wang, L. Angew. Chem., Int. Ed. 2015, 54, 8374.
67. [67]
  Miyake, Y.; Nakajima, K.; Nishibayashi, Y. Chem. Commun. 2013, 49, 7854.
68. [68]
  Chu, L.; Ohta, C.; Zuo, Z.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 10886.
69. [69]
  Lackner, G. L.; Quasdorf, K. W.; Overman, L. E. J. Am. Chem. Soc. 2013, 135, 15342.
70. [70]
  Lackner, G. L.; Quasdorf, K. W.; Pratsch, G.; Overman, L. E. J. Org. Chem. 2015, 80, 6012.
71. [71]
  Nawrat, C. C.; Jamison, C. R.; Slutskyy, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 11270.
72. [72]
  Wang, G. Z.; Shang, R.; Cheng, W. M.; Fu, Y. Org. Lett. 2015, 17, 4830.
73. [73]
  Ji, W.; Tan, H.; Wang, M.; Li, P.; Wang, L. Chem. Commun. 2016, 52, 1201.
74. [74]
  Lang, S. B.; O'Nele, K. M.; Tunge, J. A. J. Am. Chem. Soc. 2014, 136, 13606.
75. [75]
  Lang, S. B.; ONele, K. M.; Douglas, J. T.; Tunge, J. A. Chem. Eur. J. 2015, 21, 18589.
76. [76]
  Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
77. [77]
  Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2015, 54, 3216.
78. [78]
  Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
79. [79]
  Nagib1, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224.
80. [80]
  Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2012, 134, 9034.
81. [81]
  Sahoo, B.; Li, J. L.; Glorius, F. Angew. Chem., Int. Ed. 2015, 54, 11577.
82. [82]
  Su, Y. M.; Hou, Y.; Yin, F.; Xu, Y. M.; Li, Y.; Zheng, X.; Wang, X. S. Org. Lett. 2014, 16, 2958.
83. [83]
  Tomita, R.; Yasu, Y.; Koike, T.; Akita, M. Angew. Chem., Int. Ed. 2014, 53, 7144.
84. [84]
  Wolf, M. O.; Sammis, G. M.; Paquin, J. F. J. Am. Chem. Soc. 2014, 136, 2637.
85. [85]
  Ventre, S.; Petronijevic, F. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 5654.
86. [86]
  Wu, X.; Meng, C.; Yuan, X.; Jia, X.; Qian, X.; Ye. J. Chem. Commun. 2015, 51, 11864.
87. [87]
  Cassani, C.; Bergonzini, G.; Wallentin, C. J. Org. Lett. 2014, 16, 4228.
88. [88]
  Nguyen, T. M.; Nicewicz, D. A. J. Am. Chem. Soc. 2013, 135, 9588.
89. [89]
  Nguyen, T. M.; Manohar, N.; Nicewicz, D. A. Angew. Chem., Int. Ed. 2014, 53, 6198.
90. [90]
  Romero, N. A.; Nicewicz, D. A. J. Am. Chem. Soc. 2014, 136, 17024.
91. [91]
  Morse, P. D.; Nicewicz, D. A. Chem. Sci. 2015, 6, 270.
92. [92]
  Griffin, J. D.; Zeller, M. A.; Nicewicz, D. A. J. Am. Chem. Soc. 2015, 137, 11340.
93. [93]
  Liu, J.; Liu, Q.; Yi, H.; Qin, C.; Bai, R.; Qi, X.; Lan, Y. Lei, A. Angew. Chem., Int. Ed. 2014, 53, 502.
1. [1]
  Tongyan Yu , Pan Xu . Visible-Light Photocatalyzed Radical Rearrangement Reaction. University Chemistry, 2025, 40(7): 169-176. doi: 10.12461/PKU.DXHX202409070
2. [2]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
3. [3]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
4. [4]
  Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . Insights into the development of 2D covalent organic frameworks as photocatalysts in organic synthesis. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-0. doi: 10.1016/j.actphy.2025.100086
5. [5]
  Bo YANG , Gongxuan LÜ , Jiantai MA . Nickel phosphide modified phosphorus doped gallium oxide for visible light photocatalytic water splitting to hydrogen. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 736-750. doi: 10.11862/CJIC.20230346
6. [6]
  Xinzhe HUANG , Lihui XU , Yue YANG , Liming WANG , Zhangyong LIU , Zhongjian WANG . Preparation and visible light responsive photocatalytic properties of BiSbO₄/BiOBr. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 284-292. doi: 10.11862/CJIC.20240212
7. [7]
  Qin Li , Huihui Zhang , Huajun Gu , Yuanyuan Cui , Ruihua Gao , Wei-Lin Dai . In situ Growth of Cd_0.5Zn_0.5S Nanorods on Ti₃C₂ MXene Nanosheet for Efficient Visible-Light-Driven Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2025, 41(4): 2402016-0. doi: 10.3866/PKU.WHXB202402016
8. [8]
  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
9. [9]
  Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO₂ mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398
10. [10]
  Jie Li , Huida Qian , Deyang Pan , Wenjing Wang , Daliang Zhu , Zhongxue Fang . Efficient Synthesis of Anethaldehyde Induced by Visible Light. University Chemistry, 2024, 39(4): 343-350. doi: 10.3866/PKU.DXHX202310076
11. [11]
  Yuanqing Wang , Yusong Pan , Hongwu Zhu , Yanlei Xiang , Rong Han , Run Huang , Chao Du , Chengling Pan . Enhanced Catalytic Activity of Bi₂WO₆ for Organic Pollutants Degradation under the Synergism between Advanced Oxidative Processes and Visible Light Irradiation. Acta Physico-Chimica Sinica, 2024, 40(4): 2304050-0. doi: 10.3866/PKU.WHXB202304050
12. [12]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
13. [13]
  Yi Yang , Xin Zhou , Miaoli Gu , Bei Cheng , Zhen Wu , Jianjun Zhang . Femtosecond transient absorption spectroscopy investigation on ultrafast electron transfer in S-scheme ZnO/CdIn₂S₄ photocatalyst for H₂O₂ production and benzylamine oxidation. Acta Physico-Chimica Sinica, 2025, 41(6): 100064-0. doi: 10.1016/j.actphy.2025.100064
14. [14]
  Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047
15. [15]
  Hui-Ying Chen , Hao-Lin Zhu , Pei-Qin Liao , Xiao-Ming Chen . Integration of Ru(Ⅱ)-Bipyridyl and Zinc(Ⅱ)-Porphyrin Moieties in a Metal-Organic Framework for Efficient Overall CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306046-0. doi: 10.3866/PKU.WHXB202306046
16. [16]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
17. [17]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
18. [18]
  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
19. [19]
  Yuanyi Lu , Jun Zhao , Hongshuang Li . Silver-Catalyzed Ring-Opening Minisci Reaction: Developing a Teaching Experiment Suitable for Undergraduates. University Chemistry, 2024, 39(11): 225-231. doi: 10.3866/PKU.DXHX202401088
20. [20]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(4068)
HTML views(1258)

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