Photocatalytic Reactions Involving Diazo Compounds as Radical Precursors

doi:10. 6023/cjoc202207016

Abstract

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,photocatalytic generation of radicals from diazo compounds have made remarkable development. In this review,we will summarize recent developments in this research field which mainly focuses 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

Cite this article

Xie, Yang, Xuan, Jun. Photocatalytic Reactions Involving Diazo Compounds as Radical Precursors[J]. Chinese Journal of Organic Chemistry, doi: 10. 6023/cjoc202207016.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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.
(b) Huang, C.-Y.; Li, J.-B.; Li, C.-J.Chem. Sci. 2022,13, 5465.
(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.
(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.
(b) Cai, B.-G.; Li, Q.; Zhang, Q.; Li, L.; Xuan, J.Org. Chem. Front. 2021,8, 5982.
(c) Zhou, S.-J.; Cai, B.-G.; Hu, C.-X.; Cheng, X.; Li, L.; Xuan, J.Chin. Chem. Lett. 2021,32, 2577.
(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.
(b) Cai, B.-G.; Luo, S.-S.; Li, L.; Li, L.; Xuan, J.; Xiao, W.-J. CCS Chem. 2020,2, 2764.
(c) Cai, B.-G.; Li, L.; Xu, G.-Y.; Xiao, W.-J; Xuan, J.Photochem. Photobiol. Sci. 2021,20, 823.
(d) Cheng, X.; Cai, B.-G.; Mao, H.; Lu, J.; Li, L.; Wang, K.; Xuan, J.Org. Lett. 2021,23, 4109.
(e) Ye, C.; Cai, B.-G.; Lu, J.; Cheng, X.; Li, L.; Pan, Z.-W. Xuan, J.J. Org. Chem.2021,86, 1012.
[8] Z, Chen.; Zheng, Y.; Ma, J.-A.;Angew. Chem., Int. Ed. 2017,56, 4569.
[9] Zhang Yan.; 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
(b) Li, L.; Chen, J.-J.; Li, Y.-J.; Bu, X.-B.; L, Qun.; Zhao, Y.-L.Angew. Chem., Int. Ed. 2015,5, 12107.
(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.
(b) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C.Chem. Rev. 2013,113, 5322.
(c) Chen, Y.; Lu, L.-Q.; Yu, D.-G.; Zhu, C.-J.; Xiao, W.-J.Sci. China. Chem. 2019,62, 24.
(d) Cai, B.-G.; Xuan, J.; Xiao, W.-J.;Sci. Bull. 2019,64, 337.
(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.Nature2018,554, 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.
(b) Baumann, M.; Baxendale, I. R.J. Org. Chem. 2013,9, 2265.
(c) Khanfar, M. A.; Hill, R. A.; Kaddoumi, A.; El Sayed, K. A.J. Med. Chem.2010,53, 8534.
(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.
(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.
(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.
(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] Dötz 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.
(b) Devi, L.; Pokhriyal, A.; Shekhar, S.; Kant, R.; Mukherjee, S.; Rastog, N.Asian.J. Org. Chem.2021,10, 3328.
(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.
(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 Ł. 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) Dömling, A.; Wang, W.; Wang, K.;Chem. Rev.2012,112, 3083.
(b) Zhi, S.-J.; Ma, X.-M.; Zheng, W.Org. Biomol. Chem. 2019,17, 7632.
(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.
(b) Baumgartner, T.Acc. Chem. Res. 2014,47, 1613.
(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.
(b) Pan, D.; Nie, G.; Jiang, S.; Li, T.; Jin, Z.Org. Chem. Front.2020,7, 2349.
(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.
(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,DOI :10.1039/D2CC02414D
[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.
(b) Li, W.-Y.; Zhou, L.Green. Chem. 2021, 23, 6652.

重氮化合物作为自由基前体参与的光催化反应