Electroreductive deuteroarylation of alkenes enabled by an organo-mediator

Xinling Li; Jianfeng Zhou; Weijie Deng; Ziliang Wang; Yating Wen; Zhenjie Li; Youai Qiu; Yubing Huang

doi:10.1039/d4sc03049d

journal article Open Access Jan 01, 2024

Electroreductive deuteroarylation of alkenes enabled by an organo-mediator

Xinling Li Jianfeng Zhou

Weijie Deng Ziliang Wang Yating Wen Zhenjie Li Youai Qiu

Yubing Huang

Chemical Science Vol. 15 No. 29 pp. 11418-11427 · Royal Society of Chemistry (RSC)

View at Publisher Save 10.1039/d4sc03049d

Abstract

An environmentally friendly electroreduction approach is disclosed for site-specific introduction of deuterium via anti-Markovnikov selective deuteroarylation of alkenes and aryl iodides with bipyridine as a mediator and D2O as a ‘D’ source.

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References

69

[1]

Wiberg Chem. Rev. (1955) 10.1021/cr50004a004

[2]

Pirali J. Med. Chem. (2019) 10.1021/acs.jmedchem.8b01808

[3]

Puleo J. Am. Chem. Soc. (2019) 10.1021/jacs.8b12874

[4]

Xia J. Org. Chem. (2019) 10.1021/acs.joc.9b02026

[5]

Palazzolo Angew. Chem., Int. Ed. (2019) 10.1002/anie.201813946

[6]

Li Nat. Commun. (2021) 10.1038/s41467-021-23255-0

[7]

Li Chem. Soc. Rev. (2022) 10.1039/d1cs00907a

[8]

Di Martino Nat. Rev. Drug Discovery (2023) 10.1038/s41573-023-00703-8

[9]

Anti-Markovnikov Hydroarylation of Unactivated Olefins via Pyridyl Radical Intermediates

Allyson J. Boyington, Martin-Louis Y. Riu, Nathan T. Jui

Journal of the American Chemical Society 2017 10.1021/jacs.7b03262

[10]

Gurak ACS Catal. (2018) 10.1021/acscatal.8b02717

[11]

Zhou J. Org. Chem. (2018) 10.1021/acs.joc.8b00278

[12]

Nguyen Chem. Sci. (2019) 10.1039/c8sc05445b

[13]

Yang Org. Lett. (2019) 10.1021/acs.orglett.9b02577

[14]

Kingston Acc. Chem. Res. (2020) 10.1021/acs.accounts.9b00539

[15]

Zhang J. Am. Chem. Soc. (2020) 10.1021/jacs.0c08532

[16]

Zhu ACS Cent. Sci. (2021) 10.1021/acscentsci.0c01532

[17]

Electrochemical synthesis of carbamo(dithioperoxo)thioates through the dehydrogenation coupling of thiols and amines and the insertion of CS2

Qian Wang, Chengjian Xu, Yangyang Wang et al.

Green Chem. 2022 10.1039/d2gc02512d

[18]

Fang Chem. Commun. (2023) 10.1039/d3cc02852f

[19]

Liu Acc. Chem. Res. (2023) 10.1021/acs.accounts.3c00192

[20]

Zhang J. Am. Chem. Soc. (2023) 10.1021/jacs.3c04864

[21]

Electrohydrogenation of Nitriles with Amines by Cobalt Catalysis

Tiantian Wang, Fangfang He, Wei Jiang et al.

Angewandte Chemie International Edition 2024 10.1002/anie.202316140

[22]

Zhang Org. Lett. (2024) 10.1021/acs.orglett.3c03820

[23]

Electrochemical Oxidation Induced Selective C–C Bond Cleavage

Shi-Hui Shi, Ning Jiao

Chemical Reviews 2021 10.1021/acs.chemrev.0c00335

[24]

Deng Org. Lett. (2023) 10.1021/acs.orglett.3c03984

[25]

Gao J. Am. Chem. Soc. (2023) 10.1021/jacs.3c03337

[26]

Electrochemical Late-Stage Functionalization

Suman Dana, Hao Long, Yanjun Li et al.

Chemical Reviews 2023 10.1021/acs.chemrev.3c00158

[27]

Rein Chem. Soc. Rev. (2023) 10.1039/d3cs00511a

[28]

Li Curr. Opin. Electrochem. (2023) 10.1016/j.coelec.2023.101312

[29]

Redox catalysis in organic electrosynthesis: basic principles and recent developments

Robert Francke, R. Daniel Little

Chemical Society Reviews 2014 10.1039/c3cs60464k

[30]

Rafiee ChemElectroChem (2014) 10.1002/celc.201300016

[31]

Rafiee J. Am. Chem. Soc. (2015) 10.1021/jacs.5b09672

[32]

Liu Org. Biomol. Chem. (2018) 10.1039/c8ob00063h

[33]

Nutting Chem. Rev. (2018) 10.1021/acs.chemrev.7b00763

[34]

Xiong J. Am. Chem. Soc. (2018) 10.1021/jacs.8b00391

[35]

Xiong Acc. Chem. Res. (2019) 10.1021/acs.accounts.9b00472

[36]

Galvin J. Am. Chem. Soc. (2020) 10.1021/jacs.0c09605

[37]

Wang Acc. Chem. Res. (2020) 10.1021/acs.accounts.9b00544

[38]

Liu J. Am. Chem. Soc. (2021) 10.1021/jacs.1c09341

[39]

Feng Angew. Chem., Int. Ed. (2022) 10.1002/anie.202115178

[40]

Hosseini J. Am. Chem. Soc. (2022) 10.1021/jacs.2c07305

[41]

Stergiou Cell Rep. Phys. Sci. (2022) 10.1016/j.xcrp.2022.100914

[42]

Zhang Angew. Chem., Int. Ed. (2022) 10.1002/anie.202212131

[43]

Reid J. Am. Chem. Soc. (2023) 10.1021/jacs.2c10033

[44]

Badalyan Nature (2016) 10.1038/nature18008

[45]

Wang J. Am. Chem. Soc. (2021) 10.1021/jacs.1c08671

[46]

Cribari ACS Catal. (2022) 10.1021/acscatal.2c03424

[47]

Hoque J. Am. Chem. Soc. (2022) 10.1021/jacs.2c05974

[48]

Park Chem. Commun. (2023) 10.1039/d3cc01197f

[49]

Sharma ACS Catal. (2023) 10.1021/acscatal.2c06361

[50]

Zhao J. Org. Chem. (2023) 10.1021/acs.joc.2c02537

Showing 50 of 69 references

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Details

Published: Jan 01, 2024
Vol/Issue: 15(29)
Pages: 11418-11427
License: View

Authors

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Xinling Li