Electrochemical Difunctionalization of Alkenes

Jing-Hao Qin; Ning Nan; Jin-Heng Li

doi:10.1055/a-2036-2074

Synthesis, Table of Contents

Synthesis 2023; 55(18): 2843-2859
DOI: 10.1055/a-2036-2074

short review

Special Issue Electrochemical Organic Synthesis

Electrochemical Difunctionalization of Alkenes

Authors

Jing-Hao Qin∗

^aState Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. of China

^bKey Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, P. R. of China
Ning Nan

^aState Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. of China

^bKey Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, P. R. of China
Jin-Heng Li∗

^aState Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. of China

^bKey Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, P. R. of China

^cState Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China

^dSchool of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, P. R. of China

Abstract

All articles of this category

Abstract

The electrochemical alkene difunctionalization reaction has become a powerful and sustainable tool for the efficient construction of vicinal difunctionalized structures in organic synthesis. Since only electrons are used as the redox agents, electrochemical alkene difunctionalization avoids the need for additional redox catalysts, metal catalysts, or chemical oxidants and does not generate chemical waste. Herein we summarize the latest contributions in the electrochemical difunctionalization of alkenes over the last 3–4 years. We discuss in detail the reaction features, scope, limitations, and mechanistic rationalizations of three categories of alkene difunctionalization methods: (1) electrochemical alkene difunctionalization terminated by nucleophiles, (2) electrochemical difunctionalization of alkenes terminated by radicals, and (3) electrochemical alkene difunctionalization terminated by functionality migration.

1 Introduction

2 Electrochemical Alkene Difunctionalization Terminated by Nucleophiles

2.1 Sulfonylative Difunctionalization of Alkenes

2.2 Sulfurizative/Sulfoxidative Difunctionalization of Alkenes

2.3 Azidotetrazolation of Alkenes

2.4 Trifluoromethylative Difunctionalization of Alkenes

2.5 Diarylation of Alkenes

3 Electrochemical Difunctionalization of Alkenes Terminated by Radicals

3.1 Direct Radical-Coupling-Enabled Alkene Difunctionalization

3.2 Metal-Mediated Radical Transfer Coupling Enabled Alkene Difunctionalization

3.3 Metalloid-Mediated Radical Transfer Coupling Enabled Alkene Difunctionalization

4 Electrochemical Alkene Difunctionalization Terminated by Functionality Migration

5 Summary and Outlook

Key words

electrochemistry - alkene difunctionalization - radical - radical transfer coupling - functionality migration

Full Text

References

References

For selected reviews, see:

1a Surhone LM, Tennoe MT, Henssonow SF. Vicinal Difunctionalization . Betascript Publishing; Mauritius: 2010
1b Song R.-J, Liu Y, Xie Y.-X, Li J.-H. Synthesis 2015; 47: 1195
1c Chen J.-R, Yu X.-Y, Xiao W.-J. Synthesis 2015; 47: 604
1d Yin G, Mu X, Liu G. Acc. Chem. Res. 2016; 49: 2413
1e Petrone DA, Ye J, Lautens M. Chem. Rev. 2016; 116: 8003
1f Dhungana RK, Kc S, Basnet P, Giri R. Chem. Rec. 2018; 18: 1314
1g Giri R, Kc S. J. Org. Chem. 2018; 83: 3013
1h Zhang J.-S, Liu L, Chen T, Han L.-B. Chem. Asian J. 2018; 13: 2277
1i Fujihara T, Tsuji Y. Synthesis 2018; 50: 1737
1j Mei H, Yin Z, Liu J, Sun H, Han J. Chin. J. Chem. 2019; 37: 292
1k Lin J, Song R.-J, Hu M, Li J.-H. Chem. Rec. 2019; 19: 440
1l Ping Y, Li Y, Zhu J, Kong W. Angew. Chem. Int. Ed. 2019; 58: 1562
1m Wu Y.-C, Xiao Y.-T, Yang Y.-Z, Song R.-J, Li J.-H. ChemCatChem 2020; 12: 5312
1n Derosa J, Apolinar O, Kang T, Tran VT, Engle KM. Chem. Sci. 2020; 11: 4287
1o Dhungana RK, Sapkota RR, Niroula D, Giri R. Chem. Sci. 2020; 11: 9757
1p Diccianni J, Lin Q, Diao T. Acc. Chem. Res. 2020; 53: 906
1q Li Y, Wu D, Cheng H.-G, Yin G. Angew. Chem. Int. Ed. 2020; 59: 7990
1r Luo Y.-C, Xu C, Zhang X. Chin. J. Chem. 2020; 38: 1371
1s Qi X, Diao T. ACS Catal. 2020; 10: 8542
1t Lu F.-D, He G.-F, Lu L.-Q, Xiao W.-J. Green Chem. 2021; 23: 5379
1u Wickham LM, Giri R. Acc. Chem. Res. 2021; 54: 3415
1v Wang Y, Bao Y, Tang M, Ye Z, Yuan Z, Zhu G. Chem. Commun. 2022; 58: 3847
1w Luo M.-J, Xiao Q, Li J.-H. Chem. Soc. Rev. 2022; 51: 7206

2a Francke R, Little RD. Chem. Soc. Rev. 2014; 43: 2492
2b Yan M, Kawamata Y, Baran PS. Chem. Rev. 2017; 117: 13230
2c Sauer GS, Lin S. ACS Catal. 2018; 8: 5175
2d Xiong P, Xu H.-C. Acc. Chem. Res. 2019; 52: 3339
2e Röckl JL, Pollok D, Franke R, Waldvogel SR. Acc. Chem. Res. 2020; 53: 45
2f Siu JC, Fu N, Lin S. Acc. Chem. Res. 2020; 53: 547
2g Wang P, Gao X, Huang P, Lei A. ChemCatChem 2020; 12: 27

3a Moeller KD. Chem. Rev. 2018; 118: 4817
3b Tang S, Liu Y, Lei A. Chem 2018; 4: 27
3c Wiebe A, Gieshoff T, Möhle S, Rodrigo E, Zirbes M, Waldvogel SR. Angew. Chem. Int. Ed. 2018; 57: 5594
3d Meyer TH, Choi I, Tian C, Ackermann L. Chem 2020; 6: 2484
3e Zhang B, Gao Y, Hioki Y, Oderinde MS, Qiao JX, Rodriguez KX, Zhang H.-J, Kawamata Y, Baran PS. Nature 2022; 606: 313

4a Nguyen BH, Redden A, Moeller KD. Green Chem. 2014; 16: 69
4b Schultz DM, Yoon TP. Science 2014; 343: 1239176
4c Horn EJ, Rosen BR, Baran PS. ACS Cent. Sci. 2016; 2: 302

5a Yoshida J.-i, Kataoka K, Horcajada R, Nagaki A. Chem. Rev. 2008; 108: 2265
5b Sperry JB, Wright DL. Chem. Soc. Rev. 2006; 35: 605
5c Moeller KD. Tetrahedron 2000; 56: 9527

6a Solladie G, Frechou C, Demailly G, Greck C. J. Org. Chem. 1986; 51: 1912
6b Oida S, Tajima Y, Konosu T, Nakamura Y, Somada A, Tanaka T, Habuki S, Harasaki T, Kamai Y, Fukuoka T, Ohya S, Yasuda H. Chem. Pharm. Bull. 2000; 48: 694
6c Teall M, Oakley P, Harrison T, Shaw D, Kay E, Elliott J, Gerhard U, Castro JL, Shearman M, Ball RG, Tsou NN. Bioorg. Med. Chem. Lett. 2005; 15: 2685
6d Meadows DC, Gervay-Hague J. Med. Res. Rev. 2006; 26: 793
6e Alba A.-NR, Companyó X, Rios R. Chem. Soc. Rev. 2010; 39: 2018
6f Nielsen M, Jacobsen CB, Holub N, Paixão MW, Jørgensen KA. Angew. Chem. Int. Ed. 2010; 49: 2668
6g Duan L, Qiao J, Sun Y, Qiu Y. Adv. Mater. 2011; 23: 1137
6h Nicolaou KC, Hale CR. H, Nilewski C, Ioannidou HA. Chem. Soc. Rev. 2012; 41: 5185
6i Han J, Soloshonok VA, Klika KD, Drabowicz J, Wzorek A. Chem. Soc. Rev. 2018; 47: 1307
6j Scott KA, Njardarson JT. Top. Curr. Chem. 2018; 376: 5

7 Luo M.-J, Liu B, Li Y, Hu M, Li J.-H. Adv. Synth. Catal. 2019; 361: 1538
8 Yuan Y, Cao Y, Lin Y, Li Y, Huang Z, Lei A. ACS Catal. 2018; 8: 10871
9 Ye Z.-P, Gao J, Duan X.-Y, Guan J.-P, Liu F, Chen K, Xiao J.-A, Xiang H.-Y, Yang H. Chem. Commun. 2021; 57: 8969
10 Zhou P, Niu K, Song H, Liu Y, Wang Q. Green Chem. 2022; 24: 5760
11 Yu Y, Jiang Y.-M, Zhu X.-B, Lin Y.-Y, Yuan Y, Ye K.-Y. Org. Chem. Front. 2022; 9: 5586
12 Sun L, Wang L, Alhumade H, Yi H, Cai H, Lei A. Org. Lett. 2021; 23: 7724

13a Satzinger G. Drug News Perspect. 2001; 14: 197
13b Mader P, Kattner L. J. Med. Chem. 2020; 63: 14243
13c Han Y, Xing K, Zhang J, Tong T, Shi Y, Cao H, Yu H, Zhang Y, Liu D, Zhao L. Eur. J. Med. Chem. 2021; 209: 112885
13d Wan J.-L, Huang J.-M. Org. Lett. 2022; 24: 8914

14 Yu Y, Zhu X.-B, Yuan Y, Ye K.-Y. Chem. Sci. 2022; 13: 13851

15a Jeschke P. ChemBioChem 2004; 5: 570
15b Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
15c Yamazaki T, Taguchi T, Ojima I. Unique Properties of Fluorine and their Relevance to Medicinal Chemistry and Chemical Biology. In Fluorine in Medicinal Chemistry and Chemical Biology. Ojima I. Wiley-Blackwell; Chichester: 2009: 1

16 Zhang L, Zhang G, Wang P, Li Y, Lei A. Org. Lett. 2018; 20: 7396

17a Sun X, Ma H.-X, Mei T.-S, Fang P, Hu Y. Org. Lett. 2019; 21: 3167
17b Wan C, Song R.-J, Li J.-H. Org. Lett. 2019; 21: 2800
17c Zhang T.-T, Luo M.-J, Li Y, Song R.-J, Li J.-H. Org. Lett. 2020; 22: 7250

18a Harvey RG. Polycyclic Aromatic Hydrocarbons . Wiley-VCH; Weinheim: 1997
18b Hopf H. Classics in Hydrocarbon Chemistry . Wiley-VCH; Weinheim: 2000
18c Segawa Y, Ito H, Itami K. Nat. Rev. Mater. 2016; 1: 15002
18d Yan J, Chen J, Zhang S, Hu JH, Huang L, Li XS. J. Med. Chem. 2016; 59: 5264
18e Singh AK, Raj V, Saha S. Eur. J. Med. Chem. 2017; 142: 244
18f Kaur H, Singh J, Narasimhan B. BMC Chem. 2019; 13: 65
18g Qin J.-H, Luo M.-J, An D.-L, Li J.-H. Angew. Chem. Int. Ed. 2021; 60: 1861

19 Ke J, Liu W, Zhu X, Tan X, He C. Angew. Chem. Int. Ed. 2021; 60: 8744
20 Siu JC, Sauer GS, Saha A, Macey RL, Fu N, Chauviré T, Lancaster KM, Lin S. J. Am. Chem. Soc. 2018; 140: 12511
21 Fu N, Sauer GS, Saha A, Loo A, Lin S. Science 2017; 357: 575
22 Ye K.-Y, Pombar G, Fu N, Sauer GS, Keresztes I, Lin S. J. Am. Chem. Soc. 2018; 140: 2438
23 Siu JC, Parry JB, Lin S. J. Am. Chem. Soc. 2019; 141: 2825
24 Novaes LF. T, Wang Y, Liu J, Riart-Ferrer X, Lee W.-CC, Fu N, Ho JS. K, Zhang XP, Lin S. ACS Catal. 2022; 12: 14106
25 Zheng M.-W, Yuan X, Cui Y.-S, Qiu J.-K, Li G, Guo K. Org. Lett. 2018; 20: 7784
26 Zou Z, Zhang W, Wang Y, Kong L, Karotsis G, Wang Y, Pan Y. Org. Lett. 2019; 21: 1857
27 Lan J, Lin K, Zhang X, Zhu T. Green Chem. 2022; 24: 6138
28 Seastram AC, Hareram MD, Knight TM. B, Morrill LC. Chem. Commun. 2022; 58: 8658