Phenanthrolines as Energy Transfer Photocatalysts for the E → Z Isomerization of Alkenes

Xiao-Bo Chen; Jia Zhang; De-Qun Sun; Kun-Quan Chen; Xiang-Yu Chen

doi:10.1055/a-2502-8374

Synthesis, Table of Contents

Synthesis 2025; 57(12): 1928-1935
DOI: 10.1055/a-2502-8374

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Phenanthrolines as Energy Transfer Photocatalysts for the E → Z Isomerization of Alkenes

Xiao-Bo Chen

^aSchool of Life Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, P. R. China

^bSchool of Chemical Sciences, University of Chinese Academy of Sciences (UCAS), Beijing 100049, P. R. China

,

Jia Zhang

^aSchool of Life Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, P. R. China

^bSchool of Chemical Sciences, University of Chinese Academy of Sciences (UCAS), Beijing 100049, P. R. China

,

De-Qun Sun∗

^aSchool of Life Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, P. R. China

,

Kun-Quan Chen∗

^bSchool of Chemical Sciences, University of Chinese Academy of Sciences (UCAS), Beijing 100049, P. R. China

^cSchool of Pharmacy and Medical Technology, Putian University, Key Laboratory of Pharmaceutical Analysis and Laboratory Medicine (Putian University), Key Laboratory of Medical Microecology (Putian University), Putian 351100, P. R. China

,

Xiang-Yu Chen∗

^bSchool of Chemical Sciences, University of Chinese Academy of Sciences (UCAS), Beijing 100049, P. R. China

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Abstract

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Abstract

Phenanthrolines have been widely employed as chelating ligands for transition metals. Herein, this study investigates the utility of substituted o-phenanthrolines as independent photosensitizers for the E → Z isomerization of alkenes. The findings underscore the versatility of o-phenanthrolines, providing a straightforward, metal-free, and cost-effective method for synthesizing Z-alkenes.

Keywords

phenanthrolines - photocatalysis - energy-transfer - E → Z isomerization - alkenes

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References

References

1a Sammes PG, Yahioglu G. Chem. Soc. Rev. 1994; 23: 327
1b Accorsi G, Listorti A, Yoosaf K, Armaroli N. Chem. Soc. Rev. 2009; 38: 1690
1c Brandt WW, Dwyer FP, Gyarfas ED. Chem. Rev. 1954; 54: 959

2a Bencini A, Lippolis V. Coord. Chem. Rev. 2010; 254: 2096
2b Tao Y, Yang C, Qin J. Chem. Soc. Rev. 2011; 40: 2943
2c McCann M, McGinley J, Ni K, O’Connor M, Kavanagh K, McKee V, Colleran J, Devereux M, Gathergood N, Barron N, Prisecaru A, Kellett A. Chem. Commun. 2013; 49: 2341
2d Alreja P, Kaur N. RSC Adv. 2016; 6: 23169
2e Wu K, Zhang T, Zhan L, Zhong C, Gong S, Lu Z.-H, Yang C. Adv. Opt. Mater. 2016; 4: 1558
2f Zhang Y, Wu J, Song J, Chen Z, He J, Wang X, Liu H, Chen S, Qu J, Wong W.-Y. Adv. Electron. Mater. 2019; 5: 1800677
2g Tashiro S, Shimizu S, Kuritani M, Shionoya M. Dalton Trans. 2020; 49: 13948
2h Yang X.-G, Lu X.-M, Zhai Z.-M, Qin J.-H, Chang X.-H, Han M.-L, Li F.-F, Ma L.-F. Inorg. Chem. Front. 2020; 7: 2224
2i Li J, Nguyen HM. Acc. Chem. Res. 2022; 55: 3738
2j Queffélec C, Pati PB, Pellegrin Y. Chem. Rev. 2024; 124: 6700

3 Bawden JC, Francis PS, DiLuzio S, Hayne DJ, Doeven EH, Truong J, Alexander R, Henderson LC, Gómez DE, Massi M, Armstrong BI, Draper FA, Bernhard S, Connell TU. J. Am. Chem. Soc. 2022; 144: 11189
4 Morozkov GV, Abel AS, Filatov MA, Nefedov SE, Roznyatovsky VA, Cheprakov AV, Mitrofanov AY, Ziankou IS, Averin AD, Beletskaya IP, Michalak J, Bucher C, Bonneviot L, Bessmertnykh-Lemeune A. Dalton Trans. 2022; 51: 13612

5a Hossain A, Bhattacharyya A, Reiser O. Science 2019; 364: eaav9713
5b Beaudelot J, Oger S, Peruško S, Phan T.-A, Teunens T, Moucheron C, Evano G. Chem. Rev. 2022; 122: 16365

6a Singh K, Staig SJ, Weaver JD. J. Am. Chem. Soc. 2014; 136: 5275
6b Molloy JJ, Metternich JB, Daniliuc CG, Watson AJ. B, Gilmour R. Angew. Chem. Int. Ed. 2018; 57: 3168
6c Bhadra M, Kandambeth S, Sahoo MK, Addicoat M, Balaraman E, Banerjee R. J. Am. Chem. Soc. 2019; 141: 6152
6d Neveselý T, Wienhold M, Molloy JJ, Gilmour R. Chem. Rev. 2021; 122: 2650
6e Qiao S, Chen K, Liu Q, Wang Z, Chen X. Chin. Chem. Lett. 2024; 35: 108979
6f Ilies L, Yoshida T, Nakamura E. J. Am. Chem. Soc. 2012; 134: 16951

7a Kudo E, Sasaki K, Kawamata S, Yamamoto K, Murahashi T. Nat. Commun. 2021; 12: 1473
7b Metternich JB, Gilmour R. J. Am. Chem. Soc. 2015; 137: 11254
7c Cai W, Fan H, Ding D, Zhang Y, Wang W. Chem. Commun. 2017; 53: 12918

8a Bao L, Cheng J.-T, Wang Z.-X, Chen X.-Y. Org. Chem. Front. 2022; 9: 973
8b Brégent T, Bouillon J.-P, Poisson T. Org. Lett. 2020; 22: 7688
8c Li H, Chen H, Zhou Y, Huang J, Yi J, Zhao H, Wang W, Jing L. Chem. Asian J. 2020; 15: 555
8d Cruché C, Neiderer W, Collins SK. ACS Catal. 2021; 11: 8829
8e Huang H, Zhang Y, Ji P, Mariano PS, Wang W. Green Synth. Catal. 2021; 2: 27

9a Zhang Q.-Q, Lin P.-P, Yang L, Tan D.-H, Feng S.-X, Wang H, Li Q. Chin. J. Org. Chem. 2020; 40: 3314
9b Song F, Wang F, Guo L, Feng X, Zhang Y, Chu L. Angew. Chem. Int. Ed. 2019; 59: 177
9c Gong L, Ye Z. Chin. J. Org. Chem. 2022; 42: 2602

10a Metternich JB, Sagebiel S, Lückener A, Lamping S, Ravoo BJ, Gilmour R. Chem. Eur. J. 2018; 24: 4228
10b Metternich JB, Artiukhin DG, Holland MC, von Bremen-Kühne M, Neugebauer J, Gilmour R. J. Org. Chem. 2017; 82: 9955
10c Livingstone K, Tenberge M, Pape F, Daniliuc CG, Jamieson C, Gilmour R. Org. Lett. 2019; 21: 9677
10d Molloy JJ, Schäfer M, Wienhold M, Morack T, Daniliuc CG, Gilmour R. Science 2020; 369: 302
10e Metternich JB, Gilmour R. J. Am. Chem. Soc. 2016; 138: 1040

11 Neveselý T, Molloy JJ, McLaughlin C, Brüss L, Daniliuc CG, Gilmour R. Angew. Chem. Int. Ed. 2022; 61: e202113600
12 Xu J, Liu N, Lv H, He C, Liu Z, Shen X, Cheng F, Fan B. Green Chem. 2020; 22: 2739
13 Yao Y, Yu Y, Shi M.-L, Lin R.-D, Li K, Wang N. J. Catal. 2023; 428: 115153
14 Fukazawa M, Takahashi F, Nogi K, Sasamori T, Yorimitsu H. Org. Lett. 2020; 22: 2303
15 Zubar V, Sklyaruk J, Brzozowska A, Rueping M. Org. Lett. 2020; 22: 5423
16 Tyszka-Gumkowska A, Peta B, Kosik K, Szepiński E, Kajetanowicz A, Grela K. New J. Chem. 2024; 48: 4976
17 Mudududdla R, Sharma R, Abbat S, Bharatam PV, Vishwakarma RA, Bharate SB. Chem. Commun. 2014; 50: 12076
18 Lempenauer L, Duñach E, Lemière G. Chem. Eur. J. 2017; 23: 10285
19 Brégent T, Bouillon J.-P, Poisson T. Org. Lett. 2020; 22: 7688

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