Taming Challenging Radical-Based Convergent Paired Electrolysis with Dual-Transition-Metal Catalysis

Liubo Li; Niankai Fu

doi:10.1055/a-2033-8632

Synlett, Inhaltsverzeichnis

Synlett 2023; 34(13): 1549-1553
DOI: 10.1055/a-2033-8632

synpacts

Taming Challenging Radical-Based Convergent Paired Electrolysis with Dual-Transition-Metal Catalysis

Liubo Li

^aBeijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function Institute of Chemistry, Chinese Academy of Sciences, 100190 Beijing, P. R. of China

,

Niankai Fu ∗

^aBeijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function Institute of Chemistry, Chinese Academy of Sciences, 100190 Beijing, P. R. of China

^bUniversity of Chinese Academy of Sciences, 100049 Beijing, P. R. of China

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Abstract

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Abstract

The past few years have witnessed a renaissance of electrochemistry in organic synthesis. This green technology replaces chemical oxidants or reductants with inexpensive electricity. Paired electrolysis refers to processes in which reactions at both electrodes are desirable. These maximize the energy economy by avoiding the waste of electrical power on sacrificial reactions. Convergent paired electrolysis is a special case in which reactive intermediates are generated simultaneously at both electrodes and then coupled. However, radical-based reactions of this type remain underexploited. The incorporation of transition-metal catalysis could be beneficial by modulating the formation and utilization of highly reactive radical species. In this article, we introduce our most recent successful implementations of this strategic design.

1 Introduction

2 Ce/Ni Dual-Catalytic Decarboxylative Arylation

3 Fe/Ni Dual-Catalytic Esterification of Aryl Halides

4 Conclusion.

Key words

convergent paired electrolysis - electrochemistry - electrocatalysis - radical reaction - transition-metal catalysis

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Referenzen

References and Notes
1 Frontana-Uribe BA, Little RD, Ibanez JG, Palma A, Vasquez-Medrano R. Green Chem. 2010; 12: 2099

For selected recent reviews, see:

2a Francke R, Little RD. Chem. Soc. Rev. 2014; 43: 2492
2b Yan M, Kawamata Y, Baran PS. Chem. Rev. 2017; 117: 13230
2c Moeller KD. Chem. Rev. 2018; 118: 4817
2d Wiebe A, Gieshoff T, Mohle S, Rodrigo E, Zirbes M, Waldvogel SR. Angew. Chem. Int. Ed. 2018; 57: 5594
2e Waldvogel SR, Lips S, Selt M, Riehl B, Kampf CJ. Chem. Rev. 2018; 118: 6706
2f Xiong P, Xu H.-C. Acc. Chem. Res. 2019; 52: 3339
2g Elsherbini M, Wirth T. Acc. Chem. Res. 2019; 52: 3287
2h Jiao K.-J, Xing Y.-K, Yang Q.-L, Qiu H, Mei T.-S. Acc. Chem. Res. 2020; 53: 300
2i Yuan Y, Yang J, Lei A. Chem. Soc. Rev. 2021; 50: 10058
2j Novaes LF. T, Liu J, Shen Y, Lu L, Meinhardt JM, Lin S. Chem. Soc. Rev. 2021; 50: 7941
2k Ma C, Fang P, Liu D, Jiao K.-J, Gao P.-S, Qiu H, Mei T.-S. Chem. Sci. 2021; 12: 12866
2l Xu C, Lei A, Mei T.-S, Xu H.-C, Xu K, Zeng C. CCS Chem. 2022; 4: 1120

3a Zhang W, Hong N, Song L, Fu N. Chem. Rec. 2021; 21: 2574
3b Marken F, Cresswell AJ, Bull SD. Chem. Rec. 2021; 21: 2585
3c Sbei N, Hardwick T, Ahmed N. ACS Sustainable Chem. Eng. 2021; 9: 6148

4 For an example of parallel paired electrosynthesis in an industrial setting, see: Pütter H, Hannebaum H. US 6063256 2000
5 For a recent example, see: Chadderdon XH, Chadderdon DJ, Pfennig T, Shanks BH, Li W. Green Chem. 2019; 21: 6210
6 For a recent example, see: Kawamata Y, Vantourout JC, Hickey DP, Bai P, Chen L, Hou Q, Qiao W, Barman K, Edwards MA, Garrido-Castro AF, deGruyter JN, Nakamura H, Knouse K, Qin C, Clay KJ, Bao D, Li C, Starr JT, Garcia-Irizarry C, Sach N, White HS, Neurock M, Minteer SD, Baran PS. J. Am. Chem. Soc. 2019; 141: 6392
7 Zhang S, Findlater M. Chem. Eur. J. 2022; 28: e202201152

For selected recent examples, see:

8a Ma Y, Yao X, Zhang L, Ni P, Cheng R, Ye J. Angew. Chem. Int. Ed. 2019; 58: 16548
8b Ma Y, Hong J, Yao X, Liu C, Zhang L, Fu Y, Sun M, Cheng R, Li Z, Ye J. Org. Lett. 2021; 23: 9387
8c Zhang L, Hu X. Chem. Sci. 2020; 11: 10786
8d Wang Y, Deng L, Wang X, Wu Z, Wang Y, Pan Y. ACS Catal. 2019; 9: 1630
8e Zou Z, Li H, Huang M, Zhang W, Zhi S, Wang Y, Pan Y. Org. Lett. 2021; 23: 8252
8f Walker BR, Sevov CS. ACS Catal. 2019; 9: 7197
8g Yu M, Wang H, Gao Y, Bu F, Cong H, Lei A. Cell Rep. Phys. Sci. 2021; 2: 100476
8h Luo J, Hu B, Wu W, Hu M, Liu TL. Angew. Chem. Int. Ed. 2021; 60: 6107
8i Daili F, Ouarti A, Pinaud M, Kribii I, Sengmany S, Le Gall E, Léonel E. Eur. J. Org. Chem. 2020; 3452
8j Bai Y, Liu N, Wang S, Wang S, Ning S, Shi L, Cui L, Zhang Z, Xiang J. Org. Lett. 2019; 21: 6835
8k Wang Z.-H, Wei L, Jiao K.-J, Ma C, Mei T.-S. Chem. Commun. 2022; 58: 8202
8l Chen Y.-J, Deng W.-H, Guo J.-D, Ci R.-N, Zhou C, Chen B, Li X.-B, Guo X.-N, Liao R.-Z, Tung C.-H, Wu L.-Z. J. Am. Chem. Soc. 2022; 144: 17261

9 Mo Y, Lu Z, Rughoobur G, Patil P, Gershenfeld N, Akinwande AI, Buchwald SL, Jensen KF. Science 2020; 368: 1352

10a Song L, Fu N. In Comprehensive Organometallic Chemistry IV, Vol. 13, Chap. 13.08. Parkin G, Meyer K, O’Hare D. Elsevier; Amsterdam: 2022: 339
10b Lu J, Wang Y, McCallum T, Fu N. iScience 2020; 23: 101796
10c Levin MD, Kim S, Toste FD. ACS Cent. Sci. 2016; 2: 293
10d Skubi KL, Blum TR, Yoon TP. Chem. Rev. 2016; 116: 10035
10e Twilton J, Le C, Zhang P, Shaw MH, Evans RW, MacMillan DW. C. Nat. Rev. Chem. 2017; 1: 0052
10f Chan AY, Perry IB, Bissonnette NB, Buksh BF, Edwards GA, Frye LI, Garry OL, Lavagnino MN, Li BX, Liang Y, Mao E, Millet A, Oakley JV, Reed NL, Sakai HA, Seath CP, MacMillan DW. C. Chem. Rev. 2022; 122: 1485

11 Yang K, Lu J, Li L, Luo S, Fu N. Chem. Eur. J. 2022; 28: e202202370

For recent reviews and perspectives on ligand-to-metal charge transfer in organic synthesis, see:

12a Tsurugi H, Mashima K. J. Am. Chem. Soc. 2021; 143: 7879
12b Abderrazak Y, Bhattacharyya A, Reiser O. Angew. Chem. Int. Ed. 2021; 60: 21100
12c Gavelle S, Innocent M, Aubineau T, Guérinot A. Adv. Synth. Catal. 2022; 364: 4189. For recent examples of the use of Ce as a ligandto-metal charge-transfer catalyst, see:
12d Chen Y, Wang X, He X, An Q, Zuo Z. J. Am. Chem. Soc. 2021; 143: 4896
12e Yatham VR, Bellotti P, König B. Chem. Commun. 2019; 55: 3489
12f Shirase S, Tamaki S, Shinohara K, Hirosawa K, Tsurugi H, Satoh T, Mashima K. J. Am. Chem. Soc. 2020; 142: 5668
12g Lai X.-L, Shu X.-M, Song J, Xu H.-C. Angew. Chem. Int. Ed. 2020; 59: 10626
12h Wang Y, Li L, Fu N. ACS Catal. 2022; 12: 10661
12i Lai X.-L, Chen M, Wang Y, Song J, Xu H.-C. J. Am. Chem. Soc. 2022; 144: 20201
12j Yuan Y, Yang J, Zhang J. Chem. Sci. 2023; 14: 705
12k Yang K, Wang Y, Luo S, Fu N. Chem. Eur. J. 2023; in press; DOI:

13a Zuo Z, Ahneman DT, Chu L, Terrett JA, Doyle AG, MacMillan DW. Science 2014; 345: 437
13b Prieto Kullmer CN, Kautzky JA, Krska SW, Nowak T, Dreher SD, MacMillan DW. C. Science 2022; 376: 532

14 Ce(IV) carboxylates can be stored for days at room temperature when kept in darkness, see: Sheldon RA, Kochi JK. J. Am. Chem. Soc. 1968; 90: 6688
15 A relatively stable aryl Ni(II) complex was synthesized and isolated (see Figure 4)
16 Xue P, Li L, Fu N. Org. Lett. 2022; 24: 7595

17a Peters BK, Rodriguez KX, Reisberg SH, Beil SB, Hickey DP, Kawamata Y, Collins M, Starr J, Chen L, Udyavara S, Klunder K, Gorey TJ, Anderson SL, Neurock M, Minteer SD, Baran PS. Science 2019; 363: 838
17b Truesdell BL, Hamby TB, Sevov CS. J. Am. Chem. Soc. 2020; 142: 5884
17c Walker BR, Manabe S, Brusoe AT, Sevov CS. J. Am. Chem. Soc. 2021; 143: 6257