Photoelectrochemical Cerium Catalysis via Ligand-to-Metal Charge Transfer: A Rising Frontier in Sustainable Organic Synthesis

Yuying Wang; Siyuan Liu; Jiangsheng Han; Ling Wang; Jianbin Chen

doi:10.1055/a-2044-2140

Synthesis, Table of Contents

Synthesis 2023; 55(18): 2860-2872
DOI: 10.1055/a-2044-2140

short review

Special Issue Electrochemical Organic Synthesis

Photoelectrochemical Cerium Catalysis via Ligand-to-Metal Charge Transfer: A Rising Frontier in Sustainable Organic Synthesis

Yuying Wang‡

^aShandong Provincial Key Laboratory of Molecular Engineering, School of Chemistry and Chemical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, P. R. of China

,

Siyuan Liu‡

^aShandong Provincial Key Laboratory of Molecular Engineering, School of Chemistry and Chemical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, P. R. of China

,

Jiangsheng Han

^bShanDongWeGo Pharmaceutical CO., LTD, Weihai 264414, P. R. of China

,

Ling Wang

^aShandong Provincial Key Laboratory of Molecular Engineering, School of Chemistry and Chemical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, P. R. of China

,

Jianbin Chen∗

^aShandong Provincial Key Laboratory of Molecular Engineering, School of Chemistry and Chemical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, P. R. of China

› Author Affiliations

Abstract

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Abstract

Photoelectrochemical cerium catalysis is an emerging and rapidly developing strategy in organic synthetic. A sustainable platform is being constructed by combining the concerted energy transfer from light and electricity to cerium with the ligand-to-metal charge transfer of excited state Ce^IV species. With this powerful strategy, hard to oxidized substrates can be activated under mild conditions, contributing to broad functional group compatibility. Such as, carboxylic acids, alcohols, and the Cl anion can deliver the corresponding radicals via formal single electron transfer (SET) with a low oxidation potential. Further cooperation with other synthetic strategies, including alkoxy radical promoted hydrogen atom transfer (HAT) and β-scission, leads to the functionalization of inert C(sp ³)–H, Si–H, and C–C bonds via a mild radical pathway. In this review, recent advances in photoelectrochemical cerium catalysis are described. More importantly, as this field features some unique advantages, but is rarely explored, we hope chemists will pay more attention to this catalytic system.

1 Introduction

2 Activation of Carboxylic Acids

3 Activation of Alcohols

3.1 Alkoxy Radical Involved Hydrogen Atom Transfer

3.2 Alkoxy Radical Promoted β-Scission

4 Formal Single-Electron Oxidation of Cl Anion

5 Conclusions and Outlook

Key words

Ce catalysis - photoelectrochemistry - Ce^III/Ce^IV redox pair - photoinduced LMCT - single electron transfer

Full Text

References

References

1a Qiao Y, Schelter EJ. Acc. Chem. Res. 2018; 51: 2926
1b Ameen I, Tripathi AK, Mishra RL, Siddiqui A, Tripathi UN. J. Saudi Chem. Soc. 2019; 23: 725
1c Glaser F, Wenger OS. Coord. Chem. Rev. 2020; 405: 213129

2 George NC, Denault KA, Seshadri R. Annu. Rev. Mater. Res. 2013; 43: 481

3a Luche J.-L. J. Am. Chem. Soc. 1978; 100: 2226
3b Gemal AL, Luche J.-L. J. Am. Chem. Soc. 1981; 103: 5454
3c Hazin PN, Bruno JW. Organometallics 1987; 6: 913
3d Kunkely H, Vogler A. Inorg. Chem. Commun. 2006; 9: 1387
3e Harada T, Hasegawa R, Nishiyama K. Chem. Lett. 2014; 43: 1496

4a So Y.-M, Leung W.-H. Coord. Chem. Rev. 2017; 340: 172
4b Wu X.-P, Gagliardi L, Truhlar DG. J. Am. Chem. Soc. 2018; 140: 7904
4c Liu H, Yu J, Qiu C, Yu R, Li S, Cheng J, Wang J, Si Z, Yang S. Funct. Mater. Lett. 2021; 14: 2130097

5 Yin H, Carroll PJ, Anna JM, Schelter EJ. J. Am. Chem. Soc. 2015; 137: 9234

6a Nair V, Balagopal L, Rajan R, Mathew J. Acc. Chem. Res. 2004; 37: 21
6b Maulide N, Vanherck J.-C, Gautier A, Marko IE. Acc. Chem. Res. 2007; 40: 381
6c Nair V, Deepthi A. Chem. Rev. 2007; 107: 1862
6d Sridharan V, Menéndez JC. Chem. Rev. 2010; 110: 3805

7 Guo J.-J, Hu A, Chen Y, Sun J, Tang H, Zuo Z. Angew. Chem. Int. Ed. 2016; 55: 15319
8 Hu A, Guo J.-J, Pan H, Tang H, Gao Z, Zuo Z. J. Am. Chem. Soc. 2018; 140: 1612
9 Gavelle S, Innocent M, Aubineau T, Guérinot A. Adv. Synth. Catal. 2022; 364: 4189
10 Friedrich J, Schneider D, Bock L, Maichle-Mössmer C, Anwander R. Inorg. Chem. 2017; 56: 8114
11 Crabtree RH. Chem. Rev. 1995; 95: 987
12 Hu A, Guo J.-J, Pan H, Zuo Z. Science 2018; 361: 668
13 Yang Q, Wang Y.-H, Qiao Y, Gau M, Carroll PJ, Walsh PJ, Schelter EJ. Science 2021; 372: 847
14 An Q, Xing Y.-Y, Pu R, Jia M, Chen Y, Hu A, Zhang S.-Q, Yu N, Du J, Zhang Y, Chen J, Liu W, Hong X, Zuo Z. J. Am. Chem. Soc. 2023; 145: 359

15a Jiang Y, Xu K, Zeng C. Chem. Rev. 2018; 118: 4485
15b Waldvogel SR, Lips S, Selt M, Kampf CJ. Chem. Rev. 2018; 118: 6706
15c Karkas MD. Chem. Soc. Rev. 2018; 47: 5786
15d Sauer GS, Lin S. ACS Catal. 2018; 8: 5175
15e Tang S, Liu Y, Lei A. Chemistry 2018; 4: 27
15f Xiong P, Xu H.-C. Acc. Chem. Res. 2019; 52: 3339
15g Chen J, Lv S, Tian S. ChemSusChem 2019; 12: 115
15h Han X, Wang K, Zhang G, Gao W, Chen J. Adv. Synth. Catal. 2019; 361: 2804
15i Tian S, Jia X, Wang L, Li B, Liu S, Ma L, Gao W, Wei Y, Chen J. Chem. Commun. 2019; 55: 12104
15j Zhang P, Chen J, Gao W, Xiao Y, Liu C, Xu S, Yan X, Qin D. Molecules 2019; 24: 696
15k Kingston C, Palkowitz MD, Baran PS. Acc. Chem. Res. 2020; 53: 72
15l Little RD. J. Org. Chem. 2020; 85: 13375
15m Heard DM, Lennox AJ. J. Angew. Chem. Int. Ed. 2020; 59: 18866
15n Lv S, Han X, Wang J.-Y, Zhou M, Wu Y, Ma L, Niu L, Gao W, Zhou J, Hu W, Cui Y, Chen J. Angew. Chem. Int. Ed. 2020; 59: 11583
15o Shi SH, Liang Y, Jiao N. Chem. Rev. 2021; 121: 485
15p Ma C, Fang P, Liu D, Jiao KJ, Gao P, Qiu H, Mei T. Chem. Sci. 2021; 12: 12866
15q Novaes LF. T, Liu J, Shen Y, Lu L, Meinhardt JM, Lin S. Chem. Soc. Rev. 2021; 50: 7941
15r Yuan Y, Yang J, Lei A. Chem. Soc. Rev. 2021; 50: 10058
15s Beil SB, Pollok D, Waldvogel SR. Angew. Chem. Int. Ed. 2021; 60: 14750
15t Tanbouza N, Petti A, Leech MC, Caron L, Walsh JM, Lam K, Ollevier T. Org. Lett. 2022; 24: 4665
15u Guo H, Liu Y, Wen C, Wan JP. Green Chem. 2022; 24: 5058
15v Wang K, Liu X, Yang S, Tian Y, Zhou M, Zhou J, Jia X, Li B, Liu S, Chen J. Org. Lett. 2022; 24: 3471
15w Liu S, Lu Y, Sun S, Wang H, Gao W, Wang Y, Jia X, Chen J. Green Synth. Catal. 2023; 4: 71

For reviews, see:

16a Syroeshkin MA, Kuriakose F, Saverina EA, Timofeeva VA, Egorov MP, Alabugin IV. Angew. Chem. Int. Ed. 2019; 58: 5532
16b Barham JP, Konig B. Angew. Chem. Int. Ed. 2020; 59: 11732
16c Qiu Y, Scheremetjew A, Finger LH, Ackermann L. Chem. Eur. J. 2020; 26: 3241
16d Wu Y.-C, Song R.-J, Li J.-H. Org. Chem. Front. 2020; 7: 1895
16e Wu S, Kaur J, Karl TA, Tian X, Barham JP. Angew. Chem. Int. Ed. 2022; 61: e202107811

For research works, see:

17a Arnaboldi S, Benincori T, Penoni A, Vaghi L, Cirilli R, Abbate S, Longhi G, Mazzeo G, Grecchi S, Panigati M, Mussini PR. Chem. Sci. 2019; 10: 2708
17b Beranek R. Angew. Chem. Int. Ed. 2019; 58: 16724
17c Yan H, Hou Z.-W, Xu H.-C. Angew. Chem. Int. Ed. 2019; 58: 4592
17d Huang H, Strater ZM, Rauch M, Shee J, Sisto TJ, Nuckolls C, Lambert TH. Angew. Chem. Int. Ed. 2019; 58: 13318
17e Huang H, Lambert TH. Angew. Chem. Int. Ed. 2020; 59: 658
17f Huang H, Strater ZM, Lambert TH. J. Am. Chem. Soc. 2020; 142: 1698
17g Kim H, Kim H, Lambert TH, Lin S. J. Am. Chem. Soc. 2020; 142: 2087
17h Zhang W, Carpenter KL, Lin S. Angew. Chem. Int. Ed. 2020; 59: 409
17i Capaldo L, Quadri LL, Merli D, Ravelli D. Chem. Commun. 2021; 57: 4424
17j Hou ZW, Xu H.-C. ChemElectroChem 2021; 8: 1571
17k Targos K, Williams OP. Z, Wickens K. J. Am. Chem. Soc. 2021; 143: 4125
17l Shen T, Lambert TH. Science 2021; 371: 620
17m Huang H, Lambert TH. Angew. Chem. Int. Ed. 2021; 60: 11163

18a Scheffold R, Orlinski R. J. Am. Chem. Soc. 1983; 105: 7200
18b Wang F, Stahl SS. Angew. Chem. Int. Ed. 2019; 58: 6385

19a Zhang G, Kim G, Choi W. Energy Environ. Sci. 2014; 7: 954
19b Juliá F. ChemCatChem 2022; 14: e202200916

20a Hu A, Chen Y, Guo J.-J, Yu N, An Q, Zuo Z. J. Am. Chem. Soc. 2018; 140: 13580
20b Zhang K, Chang L, An Q, Wang X, Zuo Z. J. Am. Chem. Soc. 2019; 141: 10556
20c Shirase S, Tamaki S, Shinohara K, Hirosawa K, Tsurugi H, Satoh T, Mashima K. J. Am. Chem. Soc. 2020; 142: 5668
20d Abderrazak Y, Bhattacharyya A, Reiser O. Angew. Chem. Int. Ed. 2021; 60: 21100

21 Varenikov A, Shapiro E, Gandelman M. Chem. Rev. 2021; 121: 412
22 Kolbe H. Justus Liebigs Ann. Chem. 1848; 64: 339

23a Griffin JD, Zeller MA, Nicewicz DA. J. Am. Chem. Soc. 2015; 137: 11340
23b Roth HG, Romero NA, Nicewicz DA. Synlett 2015; 27: 714

24 Minisci F, Bernardi R, Bertini F, Galli R, Perchinummo M. Tetrahedron 1971; 27: 3575

25a Minisci F, Galli R, Malatesta V, Caronna T. Tetrahedron 1970; 26: 4083
25b Proctor RS. J, Phipps RJ. Angew. Chem. Int. Ed. 2019; 58: 13666

26 Lai X.-L, Shu X.-M, Song J, Xu H.-C. Angew. Chem. Int. Ed. 2020; 59: 10626
27 Yang K, Lu J, Li L, Luo S, Fu N. Chem. Eur. J. 2022; 28: e202202370

28a Sbei N, Hardwick T, Ahmed N. ACS Sustainable Chem. Eng. 2021; 9: 6148
28b Zhang W, Hong N, Song L, Fu N. Chem. Rec. 2021; 21: 2574
28c Zhang S, Findlater M. Chem. Eur. J. 2022; 28: e202201152

29a Cai C.-Y, Wu Z.-J, Liu J.-Y, Chen M, Song J, Xu H.-C. Nat. Commun. 2021; 12: 3745
29b Huang H, Steiniger KA, Lambert TH. J. Am. Chem. Soc. 2022; 144: 12567

30 Xiang J, Shang M, Kawamata Y, Lundberg H, Reisberg SH, Chen M, Mykhailiuk P, Beutner G, Collins MR, Davies A, Del Bel M, Gallego GM, Spangler JE, Starr J, Yang S, Blackmond DG, Baran PS. Nature 2019; 573: 398
31 Wang Y, Li L, Fu N. ACS Catal. 2022; 12: 10661

32a Chang X, Zhang Q, Guo C. Angew. Chem. Int. Ed. 2020; 59: 12612
32b Margarita C, Lundberg H. Catalysts 2020; 10: 982
32c Chakraborty P, Mandal R, Garg N, Sundararaju B. Coord. Chem. Rev. 2021; 444: 214065
32d Yamamoto K, Kuriyama M, Onomura O. Curr. Opin. Electrochem. 2021; 28: 100714

33a Cai C.-Y, Lai X.-L, Wang Y, Hu H.-H, Song J, Yang Y, Wang C, Xu H.-C. Nat. Catal. 2022; 5: 943
33b Fan W, Zhao X, Deng Y, Chen P, Wang F, Liu G. J. Am. Chem. Soc. 2022; 144: 21674
33c Yuan Y, Yang J, Zhang J. Chem. Sci. 2023; 14: 705

34 Lai X.-L, Chen M, Wang Y, Song J, Xu H.-C. J. Am. Chem. Soc. 2022; 144: 20201
35 Yang K, Wang Y, Luo S, Fu N. Chem. Eur. J. 2023; in press

36a Mayer JM. Acc. Chem. Res. 2011; 44: 36
36b Bietti M, Salamone M. Synlett 2014; 25: 1803
36c Salamone M, Bietti M. Acc. Chem. Res. 2015; 48: 2895
36d Capaldo L, Ravelli D. Eur. J. Org. Chem. 2017; 2017: 2056
36e Capaldo L, Quadri LL, Ravelli D. Green Chem. 2020; 22: 3376
36f Sarkar S, Cheung KP. S, Gevorgyan V. Chem. Sci. 2020; 11: 12974
36g Capaldo L, Ravelli D, Fagnoni M. Chem. Rev. 2022; 122: 1875

37 Galeotti M, Salamone M, Bietti M. Chem. Soc. Rev. 2022; 51: 2171

38a Griller D, Howard JA, Marriott PR, Scaiano JC. J. Am. Chem. Soc. 1981; 103: 619
38b Avila D, Brown C, Ingold J, Lusztyk J. J. Am. Chem. Soc. 1993; 115: 466
38c Pischel U, Nau WM. J. Am. Chem. Soc. 2001; 123: 9728
38d Finn M, Friedline R, Suleman NK, Wohl CJ, Tanko JM. J. Am. Chem. Soc. 2004; 126: 7578

39a Tsentalovich YP, Kulik LV, Gritsan NP, Yurkovskaya AV. J. Phys. Chem. A. 1998; 102: 7975
39b Weber M, Fischer H. J. Am. Chem. Soc. 1999; 121: 7381

40a Langkopf E, Schinze D. Chem. Rev. 1995; 95: 1375
40b Tamao K, Uchida M, Izumizawa T, Furukawa K, Yamaguchi S. J. Am. Chem. Soc. 1996; 118: 11974
40c Lu G, Usta H, Risko C, Wang L, Facchetti A, Ratner M, Marks TJ. J. Am. Chem. Soc. 2008; 130: 7670
40d Franz AK, Wilson SO. J. Med. Chem. 2013; 56: 388
40e Komiyama T, Minami Y, Hiyama T. ACS Catal. 2016; 7: 631
40f Ramesh R, Reddy DS. J. Med. Chem. 2018; 61: 3779

41 Blanksby S, Ellison GB. E. Acc. Chem. Res. 2003; 36: 255
42 Cekovic Z. Tetrahedron 2003; 59: 8073
43 Jiang Y, Xu K, Zeng C. CCS Chem. 2022; 4: 1796
44 Wang X.-y, Guerzo DA, Schmehl RH. J. Photochem. Photobiol., C. 2004; 5: 55
45 Xu P, López-Rojas P, Ritter T. J. Am. Chem. Soc. 2021; 143: 5349
46 Tan Z, He X, Xu K, Zeng C. ChemSusChem 2022; 15: e202102360
47 Tan Z, Jiang Y, Xu K, Zeng C. J. Catal. 2023; 417: 473

48a Wu X, Zhu C. Chem. Commun. 2019; 55: 9747
48b Tsui E, Wang H, Knowles RR. Chem. Sci. 2020; 11: 11124

49 Yamamoto K, Toguchi H, Kuriyama M, Watanabe S, Iwasaki F, Onomura O. J. Org. Chem. 2021; 86: 16177
50 Yang Z, Yang D, Zhang J, Tan C, Li J, Wang S, Zhang H, Huang Z, Lei A. J. Am. Chem. Soc. 2022; 144: 13895
51 Xu J, Cai H, Shen J, Shen C, Wu J, Zhang P, Liu X. J. Org. Chem. 2021; 86: 17816
52 Shao D, Wu Y, Hu S, Gao W, Du Y, Jia X, Liu S, Zhou M, Chen J. ACS Sustainable Chem. Eng. 2022; 10: 10294

53a Buxton GV, Bydder M, Salmon GA. J. Chem. Soc., Faraday Trans. 1998; 94: 653
53b Lei Y, Cheng S, Luo N, Yang X, An T. Environ. Sci. Technol. 2019; 53: 11170

54a Lummiss JA. M, Morse PD, Beingessner RL, Jamison TF. Chem. Rec. 2017; 17: 667
54b Brandão P, Pineiro M, Pinhoe Melo TM. V. D. Eur. J. Org. Chem. 2019; 2019: 7188
54c Horáková P, Kočí K. Molecules 2022; 27: 8536

55a Rodrigo S, Gunasekera D, Mahajan JP, Luo L. Curr. Opin. Electrochem. 2021; 28: 100712
55b Jamshidi M, Fastie C, Hilt G. Synthesis 2022; 54: 4661
55c Zhong J, Ding C, Kim H, McCallum T, Ye K. Green Synth. Catal. 2022; 3: 4661