Synthesis 2023; 55(18): 3026-3032
DOI: 10.1055/a-2147-2863
paper
Special Issue Electrochemical Organic Synthesis

Electrochemical Decarboxylative Minisci-Type Acylation of Quinoxalines under Catalyst- and External-Oxidant-Free Conditions

Yongmei Li
a   Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, Beijing, 100048, P. R. of China
b   Faculty of Environment and Life, Beijing University of Technology, Beijing 100124, P. R. of China
,
Sen Liang
a   Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, Beijing, 100048, P. R. of China
,
Dehui Wang
b   Faculty of Environment and Life, Beijing University of Technology, Beijing 100124, P. R. of China
,
Kun Xu
b   Faculty of Environment and Life, Beijing University of Technology, Beijing 100124, P. R. of China
,
Chengchu Zeng
b   Faculty of Environment and Life, Beijing University of Technology, Beijing 100124, P. R. of China
› Author Affiliations
We are grateful to the National Natural Science Foundation of China (22271009), Beijing Natural Science Foundation (2222003), and Beijing­ Municipal Education Committee Project (KZ202110005003, KM202110005006), and the funding from the Open Project Program of Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University (SPFW2021ZD01).


Abstract

An electrochemical approach for the Minisci-type acylation of quinoxalines with α-keto acids as the acyl radical precursors is reported. With the assistance of TFA as the key additive, acylated quinoxalines were constructed in synthetically useful yields. The distinguishable features of this electrochemical protocol include catalyst- and external oxidant-free conditions, and operational simplicity.

Supporting Information



Publication History

Received: 25 June 2023

Accepted after revision: 02 August 2023

Accepted Manuscript online:
02 August 2023

Article published online:
17 August 2023

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  • References


    • For selected reviews on Minisci-type reactions, see:
    • 1a Minisci F. Synthesis 1973; 1
    • 1b Tauber J, Imbri D, Opatz T. Molecules 2014; 19: 16190
    • 1c Proctor RS. J, Phipps RJ. Angew. Chem. Int. Ed. 2019; 58: 13666
    • 1d Meng W, Xu K, Guo B, Zeng C. Chin. J. Org. Chem. 2021; 41: 2621 ; and references cited therein
  • 2 Duncton MA. J. Med. Chem. Commun. 2011; 2: 1135
    • 3a Penteado F, Lopes EF, Alves D, Perin G, Jacob RG, Lenardão EJ. Chem. Rev. 2019; 119: 7113
    • 3b Li J, Zhang S, Xu K. Chin. Chem. Lett. 2021; 32: 2729

      Minisci-type acylation reactions under thermal conditions, see:
    • 4a Siddaraju Y, Lamani M, Prabhu KR. J. Org. Chem. 2014; 79: 3856
    • 4b Laha JK, Hunjan MK, Hegde S, Gupta A. Org. Lett. 2020; 22: 1442

      Minisci-type acylation reactions under photocatalytic conditions, see:
    • 5a Hafeez S, Saeed A. RSC Adv. 2021; 11: 38683
    • 5b Roy VJ, Sen P, Roy SR. Chem. Commun. 2022; 58: 1776
    • 6a Yan M, Kawamata Y, Baran PS. Chem. Rev. 2017; 117: 13230
    • 6b Hilt G. ChemElectroChem 2020; 7: 395
    • 6c Novaes LF. T, Liu J, Shen Y, Lu L, Meinhardt JM, Lin S. Chem. Soc. Rev. 2021; 50: 7941
    • 6d Zhu C, Ang NW. J, Meyer T, Qiu Y, Ackermann L. ACS Cent. Sci. 2021; 7: 415
    • 6e Cheng X, Lei A, Mei T, Xu H, Xu K, Zeng C. CCS Chem. 2022; 4: 1120
    • 6f Klein M, Waldvogel SR. Angew. Chem. Int. Ed. 2022; 61: e202204140
    • 6g Tay NE. S, Lehnherr D, Rovis T. Chem. Rev. 2022; 122: 2487
    • 6h Mahanty K, Halder A, Maiti D, Sarkar SD. Synthesis 2023; 55: 400
    • 6i Wan Q, Zhang Z, Hou Z, Wang L. Org. Chem. Front. 2023; 10: 2830
    • 7a Liu D, Liu Z, Wang Z, Ma C, Herbert S, Schirok H, Mei T. Nat. Commun. 2022; 13: 7318
    • 7b Fu Z, Ye J, Huang J. Org. Lett. 2022; 24: 5874
    • 7c Lian F, Xu K, Zeng C. Sci. Chin. Chem. 2023; 66: 540
    • 7d He T, Liang C, Huang S. Chem. Sci. 2023; 14: 143
    • 7e Lian F, Luo F, Wang M, Xu K, Zeng C. Chin. J. Chem. 2023; 41: 1583
    • 7f Luan S, Castanheiro T, Poisson T. Org. Lett. 2023; 25: 1678
    • 7g Zou L, Wang X, Xiang S, Zheng W, Lu QQ. Angew. Chem. Int. Ed. 2023; 62: e202301026
    • 7h Gausmann M, Kredit N, Christmann M. Org. Lett. 2023; 25: 2228
    • 7i Wan Q, Hou Z, Zhao X, Xie X, Wang L. Org. Lett. 2023; 25: 1008
    • 7j Lv Y, Hou Z, Li P, Wang L. Org. Chem. Front. 2023; 10: 990
    • 7k Arepally S, Kim T, Kim G, Yang H, Park JK. Angew. Chem. Int. Ed. 2023; 62: e202303460
    • 8a Wang Q, Xu K, Jiang Y, Liu Y, Sun B, Zeng C. Org. Lett. 2017; 19: 5517
    • 8b Ding H, Xu K, Zeng C. J. Catal. 2020; 381: 38

      For recent examples on electrochemical Minisci-type alkylation reactions, see:
    • 9a Xu P, Chen P, Xu H. Angew. Chem. Int. Ed. 2020; 59: 14275
    • 9b Capaldo L, Quadri LL, Merli D, Ravelli D. Chem. Commun. 2021; 57: 4424
    • 9c Tan Z, He XR, Xu K, Zeng C. ChemSusChem 2022; 15: e202102360
    • 9d Li H, Tong J, Zhu Y, Jiang C, Liu P, Sun P. Green Chem. 2022; 24: 8406
    • 9e Del Rio-Rodriguez R, Fragoso-Jarillo L, Garrido-Castro AF, Maestro MC, Fernandez-Salas JA, Aleman J. Chem. Sci. 2022; 13: 6512 ; and references cited therein
  • 10 For a recent review on the electrochemical generation of acyl radicals, see: Zhang H, Liang S, Wei D, Xu K, Zeng C. Eur. J. Org. Chem. 2022; e202200794
  • 11 Chen M, Sun N, Xu W, Zhao J, Wang G, Liu Y. Chem. Eur. J. 2015; 21: 18571
  • 12 Ali W, Behera A, Guin S, Patel BK. J. Org. Chem. 2015; 80: 5625
  • 13 Sharma R, Abdullaha M, Bharate SB. J. Org. Chem. 2017; 82: 9786