Abstract
During the past few years, electrochemical oxidative reactions through radical intermediates have emerged as an environmentally-benign, powerful platform for the facile formation of C–E (E = C, N, S, Se, O and Hal) bonds through single-electron-transfer (SET) processes at the electrodes. Functionalized unsaturated molecules and unusual structural motifs can, for instance, be directly constructed under exceedingly mild reaction conditions through initial radical attack onto alkynes. This minireview highlights the recent advances in electrooxidation in radical reactions until June 2022, with a particular focus on radical additions onto alkynes.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Brand JP, Waser J. Chem Soc Rev, 2012, 41: 4165–4179
Habrant D, Rauhala V, Koskinen AMP. Chem Soc Rev, 2010, 39: 2007–2017
Kennemur JL, Maji R, Scharf MJ, List B. Chem Rev, 2021, 121: 14649–14681
Fantoni NZ, El-Sagheer AH, Brown T. Chem Rev, 2021, 121: 7122–7154
Huang L, Arndt M, Gooßen K, Heydt H, Gooßen LJ. Chem Rev, 2015, 115: 2596–2697
Dorel R, Echavarren AM. Chem Rev, 2015, 115: 9028–9072
Meldal M, Tornøe CW. Chem Rev, 2008, 108: 2952–3015
Ackermann L. Organometallics, 2003, 22: 4367–4368
Kolb HC, Finn MG, Sharpless KB. Angew Chem Int Ed, 2001, 40: 2004–2021
Müller TE, Beller M. Chem Rev, 1998, 98: 675–704
Wang J, Chataigner I. Stereoselective Alkene Synthesis Springer Verlag. New York: Heidelberg, 2012
Flynn AB, Ogilvie WW. Chem Rev, 2007, 107: 4698–4745
Negishi E, Huang Z, Wang G, Mohan S, Wang C, Hattori H. Acc Chem Res, 2008, 41: 1474–1485
Huang HM, Bellotti P, Glorius F. Acc Chem Res, 2022, 55: 1135–1147
Coppola GA, Pillitteri S, Van der Eycken EV, You SL, Sharma UK. Chem Soc Rev, 2022, 51: 2313–2382
Pratley C, Fenner S, Murphy JA. Chem Rev, 2022, 122: 8181–8260
Xiao H, Zhang Z, Fang Y, Zhu L, Li C. Chem Soc Rev, 2021, 50: 6308–6319
Zhou H, Li ZL, Gu QS, Liu XY. ACS Catal, 2021, 11: 7978–7986
Latrache M, Hoffmann N. Chem Soc Rev, 2021, 50: 7418–7435
Leifert D, Studer A. Angew Chem Int Ed, 2020, 59: 74–108
Zhou QQ, Zou YQ, Lu LQ, Xiao WJ. Angew Chem Int Ed, 2019, 58: 1586–1604
Wei Y, Hu P, Zhang M, Su W. Chem Rev, 2017, 117: 8864–8907
Studer A, Curran DP. Angew Chem Int Ed, 2016, 55: 58–102
Dénès F, Pichowicz M, Povie G, Renaud P. Chem Rev, 2014, 114: 2587–2693
Wille U. Chem Rev, 2013, 113: 813–853
Chen P, Liu G. Synthesis, 2013, 45: 2919–2939
Koike T, Akita M. Acc Chem Res, 2016, 49: 1937–1945
Ren X, Lu Z. Chin J Catal, 2019, 40: 1003–1019
Gao B, Deng D, Huang D, Sun X. Synthesis, 2021, 53: 3522–3534
Sauer GS, Lin S. ACS Catal, 2018, 8: 5175–5187
Thadathil DA, Varghese A, Radhakrishnan KV. Asian J Org Chemis, 2021, 10: 2820–2847
Mei H, Yin Z, Liu J, Sun H, Han J. Chin J Chem, 2019, 37: 292–301
Ma C, Fang P, Liu D, Jiao KJ, Gao PS, Qiu H, Mei TS. Chem Sci, 2021, 12: 12866–12873
Xu HC, Moeller KD. J Org Chem, 2021, 86: 15845–15846
Samanta RC, Meyer TH, Siewert I, Ackermann L. Chem Sci, 2020, 11: 8657–8670
Yuan Y, Lei A. Acc Chem Res, 2019, 52: 3309–3324
Wang H, Gao X, Lv Z, Abdelilah T, Lei A. Chem Rev, 2019, 119: 6769–6787
Möhle S, Zirbes M, Rodrigo E, Gieshoff T, Wiebe A, Waldvogel SR. Angew Chem Int Ed, 2018, 57: 6018–6041
Yan M, Kawamata Y, Baran PS. Chem Rev, 2017, 117: 13230–13319
Francke R, Little RD. Chem Soc Rev, 2014, 43: 2492–2521
Yoshida J, Kataoka K, Horcajada R, Nagaki A. Chem Rev, 2008, 108: 2265–2299
Jutand A. Chem Rev, 2008, 108: 2300–2347
Sperry JB, Wright DL. Chem Soc Rev, 2006, 35: 605–621
Murray PRD, Cox JH, Chiappini ND, Roos CB, McLoughlin EA, Hejna BG, Nguyen ST, Ripberger HH, Ganley JM, Tsui E, Shin NY, Koronkiewicz B, Qiu G, Knowles RR. Chem Rev, 2022, 122: 2017–2291
Schäfer HJ. ChemCatChem, 2014, 6: 2792–2795
Kingston C, Palkowitz MD, Takahira Y, Vantourout JC, Peters BK, Kawamata Y, Baran PS. Acc Chem Res, 2020, 53: 72–83
Francke R, Little RD. Chem Soc Rev, 2014, 43: 2492–2521
Ackermann L. Electrochemistry in Organic Synthesis. Stuttgart: Thieme, 2021. 573
Chicas-Baños DF, Frontana-Uribe BA. Chem Rec, 2021, 21: 2538–2573
Ackermann L, You S-L, Oestreich M, Meng S, MacFarlane D, Yin Y. Trends Chem, 2020, 2: 275–277
Schäfer HJ. Comptes Rendus Chimie, 2011, 14: 745–765
Steckhan E, Arns T, Heineman WR, Hilt G, Hoormann D, Jörissen J, Kröner L, Lewall B, Pütter H. Chemosphere, 2001, 43: 63–73
Sauermann N, Mei R, Ackermann L. Angew Chem Int Ed, 2018, 57: 5090–5094
Clarke CJ, Tu WC, Levers O, Bröhl A, Hallett JP. Chem Rev, 2018, 118: 747–800
Yuan Y, Lei A. Nat Commun, 2020, 11: 802
For an example of electroreductive alkyne functionalization, see: Yu M, Wang H, Gao Y, Bu F, Cong H, Lei A. Cell Rep Phys Sci, 2021, 2: 100476
Chen D, Nie X, Feng Q, Zhang Y, Wang Y, Wang Q, Huang L, Huang S, Liao S. Angew Chem Int Ed, 2021, 60: 27271–27276
Yang Z, Lu F, Li H, Zhang Y, Lin W, Guo P, Wan J, Shi R, Wang T, Lei A. Org Chem Front, 2020, 7: 4064–4068
Martins GM, Shirinfar B, Hardwick T, Murtaza A, Ahmed N. Catal Sci Technol, 2019, 9: 5868–5881
Meyer TH, Choi I, Tian C, Ackermann L. Chem, 2020, 6: 2484–2496
Gandeepan P, Finger LH, Meyer TH, Ackermann L. Chem Soc Rev, 2020, 49: 4254–4272
Xu HC, Campbell JM, Moeller KD. J Org Chem, 2014, 79: 379–391
Moeller KD. Tetrahedron, 2000, 56: 9527–9554
Shono T. Tetrahedron, 1984, 40: 811–850
Schäfer HJ. Angew Chem Int Ed, 1981, 20: 911–934
Engels R, Schäfer HJ. Angew Chem Int Ed, 1978, 17: 460
Engels R, Schafer HJ, Steckhan E. Justus Liebigs Ann Chem, 1977, 1: 204–224
Xiong P, Xu HH, Song J, Xu HC. J Am Chem Soc, 2018, 140: 2460–2464
Zhu L, Xiong P, Mao ZY, Wang YH, Yan X, Lu X, Xu HC. Angew Chem Int Ed, 2016, 55: 2226–2229
Meng X, Zhang Y, Luo J, Wang F, Cao X, Huang S. Org Lett, 2020, 22: 1169–1174
Wang D, Wan Z, Zhang H, Lei A. Adv Synth Catal, 2021, 363: 1022–1027
Kong X, Yu K, Chen Q, Xu B. Adv Synth Catal, 2020, 9: 1760–1764
Hou ZW, Li L, Wang L. Org Chem Front, 2022, 9: 2815–2820
Hou ZW, Jiang T, Wu TX, Wang L. Org Lett, 2021, 23: 8585–8589
Hu J, Zeng L, Hu J, Ma R, Liu X, Jiao Y, He H, Chen S, Xu Z, Wang H, Lei A. Org Lett, 2022, 24: 289–292
Guan Z, Zhu S, Ye Y, Li X, Liu Y, Wang P, Zhang H, Huang Z, Lei A. Angew Chem Int Ed, 2022, 61: e202207059
He MX, Mo ZY, Wang ZQ, Cheng SY, Xie RR, Tang HT, Pan YM. Org Lett, 2020, 22: 724–728
Aelterman M, Sayes M, Jubault P, Poisson T. Chem Eur J, 2021, 27: 8277–8282
Li L, Hou ZW, Li P, Wang L. J Org Chem, 2022, 87: 8697–8708
Hu X, Nie L, Zhang G, Lei A. Angew Chem Int Ed, 2020, 59: 15238–15243
Liu J, Wang M, Li L, Wang L. Green Chem, 2021, 23: 4733–4740
Du WB, Wang NN, Pan C, Ni SF, Wen LR, Li M, Zhang LB. Green Chem, 2021, 23: 2420–2426
Ma Q, Li M, Chen Z, Ni SF, Wright JS, Wen LR, Zhang LB. Green Chem, 2022, 24: 4425–4431
Zhang Y, Guo D, Ye S, Liu Z, Zhu G. Org Lett, 2017, 19: 1302–1305
Zhang Y, Ye S, Ji M, Li L, Guo D, Zhu G. J Org Chem, 2017, 82: 6811–6818
Zhang Y, Zhang J, Hu B, Ji M, Ye S, Zhu G. Org Lett, 2018, 20: 2988–2992
Wen J, Shi W, Zhang F, Liu D, Tang S, Wang H, Lin XM, Lei A. Org Lett, 2017, 19: 3131–3134
Zhang Y, Ma C, Struwe J, Feng J, Zhu G, Ackermann L. Chem Sci, 2021, 12: 10092–10096
Brookes CJ, Coe PL, Pedler AE, Tatlow JC. J Chem Soc Perkin Trans 1, 1978: 202
Liang Y, Lin F, Adeli Y, Jin R, Jiao N. Angew Chem Int Ed, 2019, 58: 4566–4570
Batey RA. J Am Chem Soc, 2007, 129: 7476
Zhang Y, Ma C, Cai Z, Struwe J, Chen S, Xu J, Li S, Zeng W, Ackermann L. Green Chem, 2022, 24: 3697–3703
Yang WC, Zhang MM, Sun Y, Chen CY, Wang L. Org Lett, 2021, 23: 6691–6696
Reddy CR, Kolgave DH. J Org Chem, 2021, 86: 17071–17081
Hua J, Fang Z, Xu J, Bian M, Liu CK, He W, Zhu N, Yang Z, Guo K. Green Chem, 2019, 21: 4706–4711
Xu F, Long H, Song J, Xu HC. Angew Chem Int Ed, 2019, 58: 9017–9021
Hou ZW, Xu HC. Chin J Chem, 2020, 38: 394–398
Hou ZW, Mao ZY, Zhao HB, Melcamu YY, Lu X, Song J, Xu HC. Angew Chem Int Ed, 2016, 55: 9168–9172
Hou ZW, Mao ZY, Melcamu YY, Lu X, Xu HC. Angew Chem Int Ed, 2018, 57: 1636–1639
Hou ZW, Mao ZY, Xu HC. Org Biomol Chem, 2021, 19: 8789–8793
Hou ZW, Mao ZY, Song J, Xu HC. ACS Catal, 2017, 7: 5810–5813
Zhang LB, Geng RS, Wang ZC, Ren GY, Wen LR, Li M. Green Chem, 2020, 22: 16–21
Cai C, Lu Y, Yuan C, Fang Z, Yang X, Liu C, Guo K. ACS Sustain Chem Eng, 2022, 10: 3288–3294
Ye KY, Song Z, Sauer GS, Harenberg JH, Fu N, Lin S. Chem Eur J, 2018, 24: 12274–12279
Snider BB. Chem Rev, 1996, 96: 339–364
Zhang TS, Hao WJ, Wang R, Wang SC, Tu SJ, Jiang B. Green Chem, 2020, 22: 4259–4269
Gao Y, Mei H, Han J, Pan Y. Chem Eur J, 2018, 24: 17205–17209
Xu Y, Wu Z, Jiang J, Ke Z, Zhu C. Angew Chem Int Ed, 2017, 56: 4545–4548
You Y, Kanna W, Takano H, Hayashi H, Maeda S, Mita T. J Am Chem Soc, 2022, 144: 3685–3695
Wang B, Peng P, Ma W, Liu Z, Huang C, Cao Y, Hu P, Qi X, Lu Q. J Am Chem Soc, 2021, 143: 12985–12991
Guo Y, Wang R, Song H, Liu Y, Wang Q. Chem Commun, 2021, 57: 8284–8287
Gao Y, Hill DE, Hao W, McNicholas BJ, Vantourout JC, Hadt RG, Reisman SE, Blackmond DG, Baran PS. J Am Chem Soc, 2021, 143: 9478–9488
Zhang W, Lin S. J Am Chem Soc, 2020, 142: 20661–20670
Liu Q, Sun B, Liu Z, Kao Y, Dong BW, Jiang SD, Li F, Liu G, Yang Y, Mo F. Chem Sci, 2018, 9: 8731–8737
Wang P, Yang Z, Wang Z, Xu C, Huang L, Wang S, Zhang H, Lei A. Angew Chem Int Ed, 2019, 58: 15747–15751
Zhou Z, Yuan Y, Cao Y, Qiao J, Yao A, Zhao J, Zuo W, Chen W, Lei A. Chin J Chem, 2019, 37: 611–615
Acknowledgements
This work was supported by the Natural Science Foundation of Zhejiang Province (LY22B020001), the National Natural Science Foundation of China (21702188), the ERC Advanced Grant (101021358), and the Gottfried-Wilhelm-Leibniz award to LA (DFG).
Funding
Funding note Open access funding provided by Projekt DEAL.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest The authors declare no conflict of interest.
Rights and permissions
Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.
About this article
Cite this article
Zhang, Y., Cai, Z., Warratz, S. et al. Recent advances in electrooxidative radical transformations of alkynes. Sci. China Chem. 66, 703–724 (2023). https://doi.org/10.1007/s11426-022-1438-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-022-1438-0