Volume 12, Pages 293-303 (February 2019) Electrochemical Oxidative Clean Halogenation Using HX/NaX with Hydrogen Evolution  Yong Yuan, Anjin Yao, Yongfu Zheng, Meng Gao, Zhilin Zhou, Jin Qiao, Jiajia Hu, Baoqin Ye, Jing Zhao, Huilai Wen, Aiwen Lei  iScience  Volume 12, Pages 293-303 (February 2019) DOI: 10.1016/j.isci.2019.01.017 Copyright © 2019 The Author(s) Terms and Conditions

iScience 2019 12, 293-303DOI: (10.1016/j.isci.2019.01.017) Copyright © 2019 The Author(s) Terms and Conditions

Figure 1 Substrate Scope for Electrochemical Oxidative C-H Halogenation (A) Substrate scope of C-H chlorination. (B) Substrate scope of C-H bromination. (C) Gram-scale synthesis. Reaction conditions: carbon rod anode, platinum plate cathode, constant current = 12 mA, 1 (0.3 mmol), 2a (2.0 equiv.) or 2b (4.0 equiv.), DMF (10.5 mL), H2O (0.5 mL), 80°C, N2, 3.5 h (5.2 F/mol), isolated yields. aCH3CN (10.5 mL), H2O (0.5 mL), 75°C. b1 (2.0 equiv.), 2 (0.3 mmol). c7.0 h. iScience 2019 12, 293-303DOI: (10.1016/j.isci.2019.01.017) Copyright © 2019 The Author(s) Terms and Conditions

Figure 2 Control Experiments iScience 2019 12, 293-303DOI: (10.1016/j.isci.2019.01.017) Copyright © 2019 The Author(s) Terms and Conditions

Figure 3 Proposed Mechanism of C-H Halogenation iScience 2019 12, 293-303DOI: (10.1016/j.isci.2019.01.017) Copyright © 2019 The Author(s) Terms and Conditions

Figure 4 Substrate Scope for Electrochemical Oxidative Dibromination of Alkenes (A) Substrate scope of alkenes. (B) Gram-scale synthesis. Reaction conditions: carbon rod anode, platinum plate cathode, constant current = 12 mA, 5 (0.5 mmol), 2c (2.0 equiv.), MeCN (10.8 mL), H2O (0.2 mL), nBu4NBF4 (0.1 mmol), RT, N2, 3.0 h (2.7 F/mol), isolated yields. a2c (4.0 equiv.), 6.0 h. iScience 2019 12, 293-303DOI: (10.1016/j.isci.2019.01.017) Copyright © 2019 The Author(s) Terms and Conditions

Figure 5 Substrate Scope for Electrochemical Oxidative Dibromination of Alkynes Reaction conditions: carbon rod anode, platinum plate cathode, constant current = 12 mA, 7 (0.3 mmol), 2b (4.0 equiv.), MeCN (10.5 mL), H2O (0.5 mL), 75°C, N2, 3.5 h, isolated yields. iScience 2019 12, 293-303DOI: (10.1016/j.isci.2019.01.017) Copyright © 2019 The Author(s) Terms and Conditions

Figure 6 Mechanism Experiments iScience 2019 12, 293-303DOI: (10.1016/j.isci.2019.01.017) Copyright © 2019 The Author(s) Terms and Conditions

Figure 7 Electrochemical Oxidative C-H Bromination of Aliphatic Hydrocarbons iScience 2019 12, 293-303DOI: (10.1016/j.isci.2019.01.017) Copyright © 2019 The Author(s) Terms and Conditions