Chinese Journal of Organic Chemistry >
Photocatalytic Reactions Involving Diazo Compounds as Radical Precursors
Received date: 2022-07-07
Revised date: 2022-08-09
Online published: 2022-08-17
Supported by
National Natural Science Foundation of China(21971001); National Natural Science Foundation of China(21702001)
Diazo compounds are important synthons which have attracted condirable attentions by synthetic chemists. They can server as carbene precursors, 1,3-dipoles, C-nucleophiles, terminal N-electrophiles and radical intermediates. In recent years, the photocatalytic generation of radicals from diazo compounds has made remarkable development. In this review, the recent developments in this research field are summarized which mainly focus on the generation of diazomethyl radical, carbon radicals, carbyne radicals and allene radicals from diazo compounds. Moreover, the future development direction, as well as challenges in this field is prospected.
Key words: photoredox catalysis; diazo compounds; radical
Yang Xie , Jun Xuan . Photocatalytic Reactions Involving Diazo Compounds as Radical Precursors[J]. Chinese Journal of Organic Chemistry, 2022 , 42(12) : 4247 -4256 . DOI: 10.6023/cjoc202207016
| [1] | Gomberg, M. J. Am. Chem. Soc. 1900, 22, 757. |
| [2] | Yan, M.; Lo, J. C.; Edward, J. T.; Baran, P. S. J. Am. Chem. Soc. 2016, 138, 12692. |
| [3] | (a) Yi, H.; Zhang, G.-T.; Wang, H.-M.; Huang, Z.-Y.; Wang, J.; Singh, A. K.; Lei, A.-W. Chem. Rev. 2017, 117, 9016. |
| [3] | (b) Huang, C.-Y.; Li, J.-B.; Li, C.-J. Chem. Sci. 2022, 13, 5465. |
| [3] | (c) Kwon, K.; Simons, R. T.; Nandakumar, M.; Roizen, J, L. Chem. Rev. 2022, 122, 2353. |
| [4] | (a) Yang, Z.; Stivanin, M. L.; Jurberg, I. D.; Koenigs, R. M. Chem. Soc. Rev. 2020, 49, 6833. |
| [4] | (b) Durka, J.; Turkowska, J.; Gryko, D. ACS. Sustainable. Chem. Eng. 2021, 9, 8895. |
| [5] | Chen, Z.-L.; Empel, C.; Wang, K.; Wu, P.-P.; Cai, B.-G.; Li, L.; Koenigs, R. M.; Xuan, J. Org. Lett. 2022, 24, 2232. |
| [6] | (a) Qian, L.; Cai, B.-G.; Li, L.; Xuan, J. Org. Lett. 2021, 23, 6951. |
| [6] | (b) Cai, B.-G.; Li, Q.; Zhang, Q.; Li, L.; Xuan, J. Org. Chem. Front. 2021, 8, 5982. |
| [6] | (c) Zhou, S.-J.; Cai, B.-G.; Hu, C.-X.; Cheng, X.; Li, L.; Xuan, J. Chin. Chem. Lett. 2021, 32, 2577. |
| [6] | (d) Cai, B.-G.; Li, Q.; Li, L.; Xuan, J. Green. Synth. Catal. 2022, 3, 194. |
| [7] | (a) Lu, J.; Li, L.; He, X.-K.; Xu, G.-Y.; Xuan, J. Chin. J. Chem. 2021, 39, 1646. |
| [7] | (b) Cai, B.-G.; Luo, S.-S.; Li, L.; Li, L.; Xuan, J.; Xiao, W.-J. CCS Chem. 2020, 2, 2764. |
| [7] | (c) Cai, B.-G.; Li, L.; Xu, G.-Y.; Xiao, W.-J; Xuan, J. Photochem. Photobiol. Sci. 2021, 20, 823. |
| [7] | (d) Cheng, X.; Cai, B.-G.; Mao, H.; Lu, J.; Li, L.; Wang, K.; Xuan, J. Org. Lett. 2021, 23, 4109. |
| [7] | (e) Ye, C.; Cai, B.-G.; Lu, J.; Cheng, X.; Li, L.; Pan, Z.-W.; Xuan, J. J. Org. Chem. 2021, 86, 1012. |
| [8] | Chen, Z.; Zheng, Y.; Ma, J.-A.; Angew. Chem., Int. Ed. 2017, 56, 4569. |
| [9] | Zhang, Y.; Wang, J.-H. Chem. Commun. 2009, 5390. |
| [10] | (a) Li, Wei.; Liu, X.-H.; Hao, X.-Y.; Hu, X.-L.; Chu, Y.-Y.; Cao, W.-D.; Qin, S.; Hu, C.-W.; Lin, L.-L.; Feng, X.-M. J. Am. Chem. Soc. 2011, 133, 15268. |
| [10] | (b) Li, L.; Chen, J.-J.; Li, Y.-J.; Bu, X.-B.; L, Qun.; Zhao, Y.-L. Angew. Chem., Int. Ed. 2015, 5, 12107. |
| [10] | (c) Zhang, L.; Chen, J.-J.; Liu, S.-S.; Liang, Y.-X.; Zhao, Y.-L. Adv. Synth. Catal. 2018, 359, 351. |
| [11] | (a) Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828. |
| [11] | (b) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. |
| [11] | (c) Chen, Y.; Lu, L.-Q.; Yu, D.-G.; Zhu, C.-J.; Xiao, W.-J. Sci. China. Chem. 2019, 62, 24. |
| [11] | (d) Cai, B.-G.; Xuan, J.; Xiao, W.-J.; Sci. Bull. 2019, 64, 337. |
| [11] | (e) Xuan, J.; He, X.-K.; Xiao, W.-J. Chem. Soc. Rev. 2020, 49, 2546. |
| [12] | Wang, Z.-F.; Herraiz, A. G.; Hoyo, A. M. D.; Suero, M. G. Nature 2018, 554, 86. |
| [13] | Li, P.; Zhao, J.-J.; Shi, L.-J.; Wang, J.; Shi, X.-D.; Li, F.-W. Nat. Commun. 2018, 9, 1972. |
| [14] | Su, Y.-L.; Liu, G.-X.; Angelis, L. D.; He, R.; Al-Sayyed, A.; Schanze, K. S.; Hu, W.-H.; Qiu, H.; Doyle, M. P. ACS Catal. 2022, 12, 1357. |
| [15] | (a) Majumdar, K. C.; Chattopadhyay, S. K. Heterocycles in Natural Product Synthesis, Wiley-VCH Verlag & Co. KGaA, Weinheim, 2011. |
| [15] | (b) Baumann, M.; Baxendale, I. R. J. Org. Chem. 2013, 9, 2265. |
| [15] | (c) Khanfar, M. A.; Hill, R. A.; Kaddoumi, A.; El Sayed, K. A. J. Med. Chem. 2010, 53, 8534. |
| [15] | (d) Rapolu, S.; Alla, M.; Bommena, V. R.; Murthy, R.; Jain, N.; Bommareddy, V. R.; Bommineni, M. R. Eur. J. Med. Chem. 2013, 66, 91. |
| [16] | (a) Li, J.; Lu, X.-C.; Xu, Y.; Wen, J.-X.; Hou, G.-Q.; Liu, L. Org. Lett. 2020, 22, 9621. |
| [16] | (b) Wen, J.-X.; Zhao, W.-Y.; Gao, X.; Ren, X.-F.; Dong, C.-P.; Wang, C.-L.; Liu, L.; Li, J. J. Org. Chem. 2022, 86, 1012. |
| [17] | Zhao, W.-W.; Shao, Y.-C.; Wang, A.-N.; Huang, J.-L.; He, C.-Y.; Cui, B.-D.; Wan, N.-W.; Chen, Y.-Z.; Han, W.-Y. Org. Lett. 2021, 23, 9256. |
| [18] | Li, X.-D.; Golz, C.; Alcarazo, M. Angew. Chem. Int. Ed. 2021, 60, 6943. |
| [19] | Dong, J.-Y.; Wang, H.; Mao, S.-K.; Wang, X.; Zhou, M.-D.; Li, L. Adv. Synth. Catal. 2021, 363, 2133. |
| [20] | Huang, X.-Q.; Webster, R. D.; Harms, K.; Meggers, E. J. Am. Chem. Soc. 2016, 138, 12636. |
| [21] | (a) Jurberg, I. D.; Davies, H. M. L. Chem. Sci. 2018, 9, 5112. |
| [21] | (b) Zhang, Z.-Y.; Yadagiri, D.; Gevorgyan, V. Chem. Sci. 2019, 10, 8399. |
| [22] | Fu, X.; Tang, J.; Hua, R.-Y.; Li, X.-Q.; Kang, Z.-H.; Qiu, H.; Hu, W.-H. Org. Lett. 2022, 24, 2208. |
| [23] | (a) Boyd, M. R.; Hallock, Y. F.; Cardellina, J. H.; Manfredi, K. P.; Blunt, J. W.; McMahon, J. B. Buckheit, R. W.; Brignmann, G.; Schaffer, M.; Cragg, G. M.; Thomas, D. W. Johnson, G. J. J. Med. Chem. 1994, 37, 1740. |
| [23] | (b) Boudesocque-Delaye, L.; Agostinho, D.; Bodet, C.; Thery- Kone, I.; Allouch, H.; Gueiffer, A.; Nuzillard, J.-M.; Enguehard- Gueiffer, C. J. Nat. Prod. 2015, 78, 597. |
| [24] | D?tz, K. H. Angew. Chem. Int. Ed. 1975, 14, 644. |
| [25] | He, Y.-W.; Chen, H.-G.; Li, L.-Y.; Huang, J.; Xiao, T.-B.; Anand, D.; Zhou, L. J. Photochem. Photobiol. A Chem. 2018, 355, 220. |
| [26] | (a) Nagode, B. S.; Kant, R.; Rastogi, N. Org. Lett. 2019, 21, 6249. |
| [26] | (b) Devi, L.; Pokhriyal, A.; Shekhar, S.; Kant, R.; Mukherjee, S.; Rastog, N. Asian. J. Org. Chem. 2021, 10, 3328. |
| [26] | (c) Li, W.-Y.; Zhou, L. Org. Lett. 2021, 23, 4279. |
| [27] | Lednicer, D. Strategies for Organic Drug Synthesis and Design, John Wiley & Sons, Inc., Hoboken, 2008. |
| [28] | (a) Gibe, R.; Kerr, M. A. J. Org. Chem. 2002, 67, 6274. |
| [28] | (b) Li, Z.; Shi, Z.; He, C. J. Organomet. Chem. 2005, 690, 5049. |
| [29] | James, M. J.; Strieth-Kalthoff, F.; Sandfort, F.; Klauck, F.; Wagener, F.; Glorius, F. Chem.-Eur. J. 2019, 25, 8240. |
| [30] | Ciszewski, ?. W.; Durka, J.; Gryko, D. Org. Lett. 2019, 21, 7028. |
| [31] | Bhattacharjee, S.; Laru, S.; Samanta, S.; Singsardar, M.; Hajra, A. RSC Adv. 2020, 10, 27984. |
| [32] | (a) Do?mling, A.; Wang, W.; Wang, K.; Chem. Rev. 2012, 112, 3083. |
| [32] | (b) Zhi, S.-J.; Ma, X.-M.; Zheng, W. Org. Biomol. Chem. 2019, 17, 7632. |
| [32] | (c) Lu, F.-D.; He, G.-F.; Lu, L.-Q.; Xiao, W.-J. Green. Chem. 2021, 23, 5379. |
| [33] | Xia, Y.; Qiu, D.; Wang, J.-B. Chem. Rev. 2017, 117, 13810. |
| [34] | Guo, X.; Hu, W.-H. Acc. Chem. Res. 2013, 46, 2427. |
| [35] | Su, Y.-L.; Liu, G.-X.; Liu, J.-W.; Tram, L.; Qiu, H.; Doyle, M. P. J. Am. Chem. Soc. 2020, 142, 13846. |
| [36] | Su, Y.-L.; Liu, G.-X.; Angelis, L. D.; He, R.; Al-Sayyed, A.; Schanze, K. S.; Hu, W.-H.; Qiu, H.; Doyle, M. P. ACS Catal. 2022, 12, 1357. |
| [37] | Jiang, J.-W.; Liu, J.-J.; Yang, L.; Shao, Y.; Cheng, J.; Bao, X.-G.; Wan, X.-B.; Chem. Commun. 2015, 51, 14728. |
| [38] | Ma, N.; Guo, L.; Qi, D.; Gao, F.; Yang, C.; Xia, W.-J. Org. Lett. 2021, 23, 6278. |
| [39] | Liu, G.-X.; Liang, H.-C.; Fu, X.; Tang, J.; Hu, W.-H.; Qiu, H. Org. Lett. 2022, 24, 4908. |
| [40] | Zhang, B.; Qi, J.-Q.; Liu, Y.-H.; Li, Z.-P.; Wang, J. Org. Lett. 2022, 24, 279. |
| [41] | (a) Baumgartner, T.; Réau, R. Chem. Rev. 2006, 106, 4681. |
| [41] | (b) Baumgartner, T. Acc. Chem. Res. 2014, 47, 1613. |
| [41] | (c) Joly, D.; Bouit, P.-A.; Hissler, M. J. Mater. Chem. C 2016, 4, 3686. |
| [42] | (a) Clevenger, A. L.; Stolley, R. M.; Aderibigbe, J.; Louie, J. Chem. Rev. 2020, 120, 6124. |
| [42] | (b) Pan, D.; Nie, G.; Jiang, S.; Li, T.; Jin, Z. Org. Chem. Front. 2020, 7, 2349. |
| [42] | (c) Maddigan-Wyatt, J.; Hooper, J. F. Adv. Synth. Catal. 2021, 363, 924. |
| [43] | Jiang, H.; Jin, H.; Abdukader, A.; Lin, A.; Cheng, Y.; Zhu, C. Org. Biomol. Chem. 2013, 11, 3612. |
| [44] | (a) Wang, L.; Wu, Y.; Liu, Y.; Yang, H.; Liu, X.; Wang, J.; Li, X.; Jiang, J. Org. Lett. 2017, 19, 782. |
| [44] | (b) Gu, X.; Xie, P.; Jiang, J.; Wu, Y.; Wang, L. J. Chem. Res. 2018, 42, 63. |
| [45] | Zhou, H.-Y.; Wang, G.-G.; Wang, C.-H.; Yang, J.-Y. Org. Lett. 2022, 24, 1530. |
| [46] | Kornblum, N.; DeLaMare, H. E. J. Am. Chem. Soc. 1951, 73, 880. |
| [47] | Li, F.; Zhu, S.-Q.; Koenigs, R. M. Chem. Commun. 2022, 58, 7526. |
| [48] | Wang, X.-Y.; Tong, W.-Y.; Huang, B.; Cao, S.; Li, Y.-L.; Jiao, J.-C.; Huang, H.; Yi, Q.; Qu, S.-L.; Wang, X. J. Am. Chem. Soc. 2022, 144, 4952. |
| [49] | Li, W.-Y.; Zhou, L. Org. Lett. 2022, 24, 3976. |
| [50] | (a) Li, W.-Y.; Zhou, X.-Y.; Xiao, T.-B.; Ke, Z.-F.; Zhou, L. CCS Chem. 2022, 4, 638. |
| [50] | (b) Li, W.-Y.; Zhou, L. Green Chem. 2021, 23, 6652. |
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