Electrochemical C-H carboxylation of benzylamines
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* Corresponding author.
E-mail address: qiuyouai@nankai.edu.cn (Y. Qiu).
Citation:
Weimei Zeng, Youai Qiu. Electrochemical C-H carboxylation of benzylamines[J]. Chinese Chemical Letters,
;2026, 37(1): 111679.
doi:
10.1016/j.cclet.2025.111679
K. Huang, C.L. Sun, Z.J. Shi, Chem. Soc. Rev. 40 (2011) 2435–2452.
doi: 10.1039/c0cs00129e
Y. Cao, X. He, N. Wang, et al., Chin. J. Chem. 36 (2018) 644–659.
doi: 10.1002/cjoc.201700742
J.H. Ye, T. Ju, H. Huang, et al., Acc. Chem. Res. 54 (2021) 2518–2531.
doi: 10.1021/acs.accounts.1c00135
B. Cai, H.W. Cheo, T. Liu, et al., Angew. Chem. Int. Ed. 60 (2021) 18950–18980.
doi: 10.1002/anie.202010710
M. He, Y. Sun, B. Han, Angew. Chem. Int. Ed. 61 (2022) e202112835.
doi: 10.1002/anie.202112835
Y. Liu, P. Li, Y. Wang, et al., Angew. Chem. Int. Ed. 62 (2022) e202306679.
J. Hou, J.S. Li, J. Wu, Asian J. Org. Chem. 7 (2018) 1439–1447.
doi: 10.1002/ajoc.201800226
C.S. Yeung, Angew. Chem. Int. Ed. 58 (2019) 5492–5502.
doi: 10.1002/anie.201806285
Q.Y. Meng, T.E. Schirmer, A.L. Berger, et al., J. Am. Chem. Soc. 141 (2019) 11393–11397.
doi: 10.1021/jacs.9b05360
N. Ishida, Y. Masuda, Y. Imamura, et al., J. Am. Chem. Soc. 141 (2019) 19611–19615.
doi: 10.1021/jacs.9b12529
H. Wang, Y. Gao, C. Zhou, et al., J. Am. Chem. Soc. 142 (2020) 8122–8129.
doi: 10.1021/jacs.0c03144
M. Schmalzbauer, T.D. Svejstrup, F. Fricke, et al., Chem 6 (2020) 2658–2672.
doi: 10.1016/j.chempr.2020.08.022
Y. Liu, G.-H. Xue, Z. He, et al., J. Am. Chem. Soc. 146 (2024) 28350–28359.
J.L. Li, S.S. Zhang, L.L. Jiang, et al., Angew. Chem. Int. Ed. 64 (2024) e202420852.
H. Komatsu, Y. Fujimura, H. Senboku, et al., Synlett 3 (2001) 418–420.
C. Li, G. Yuan, H. Jiang, Chin. J. Chem. 28 (2010) 1685–1689.
doi: 10.1002/cjoc.201090285
K.J. Jiao, Z.M. Li, X.T. Xu, et al., Org. Chem. Front. 5 (2018) 2244–2248.
doi: 10.1039/c8qo00507a
S. Bazzi, G.L. Duc, E. Schulz, et al., Org. Biomol. Chem. 17 (2019) 8546–8550.
doi: 10.1039/c9ob01752f
A. Alkayal, V. Tabas, S. Montanaro, et al., J. Am. Chem. Soc. 142 (2020) 1780–1785.
doi: 10.1021/jacs.9b13305
W. Zhang, S. Lin, J. Am. Chem. Soc. 142 (2020) 20661–20670.
doi: 10.1021/jacs.0c08532
N.W.J. Ang, J.C.A. Oliveira, L. Ackermann, Angew. Chem. Int. Ed. 59 (2020) 12842–12847.
doi: 10.1002/anie.202003218
S. Tang, S. Wang, D. Zhang, et al., Chin. Chem. Lett. 35 (2024) 108660.
doi: 10.1016/j.cclet.2023.108660
H. Senboku, Chem. Rec. 21 (2021) 2354–2374.
doi: 10.1002/tcr.202100081
M.A. Stalcup, C.K. Nilles, H.J. Lee, et al., ACS Sustainable Chem. Eng. 9 (2021) 10431–10436.
doi: 10.1021/acssuschemeng.1c03073
K. Zhang, B.H. Ren, X.F. Liu, et al., Angew. Chem. Int. Ed. 61 (2022) e202207660.
doi: 10.1002/anie.202207660
G.Q. Sun, P. Yu, W. Zhang, et al., Nature 615 (2023) 67–72.
doi: 10.1038/s41586-022-05667-0
S. Chen, A. Shi, G. Yang, et al., Chin. Chem. Lett. 36 (2025) 110810.
doi: 10.1016/j.cclet.2024.110810
N. Fu, G.S. Sauer, A. Saha, et al., Science 357 (2017) 575–579.
doi: 10.1126/science.aan6206
T. Shen, T.H. Lambert, Science 371 (2021) 620–626.
doi: 10.1126/science.abf2798
D.S. Chung, S.H. Park, S. Lee, et al., Chem. Sci. 12 (2021) 5892–5897.
doi: 10.1039/d1sc00760b
S.Z. Sun, Y.M. Cai, D.L. Zhang, et al., J. Am. Chem. Soc. 144 (2022) 1130–1137.
doi: 10.1021/jacs.1c12350
R. Li, Y. Wu, C. Wang, et al., Nat. Commun. 13 (2022) 5951.
doi: 10.1038/s41467-022-33779-8
J. Zhang, B. Das, O. Verho, et al., Angew. Chem. Int. Ed. 61 (2022) e202212131.
doi: 10.1002/anie.202212131
Y. Yu, Y. Jiang, S. Wu, et al., Chin. Chem. Lett. 33 (2022) 2009–2014.
doi: 10.1016/j.cclet.2021.10.016
Z.J. Shen, C. Zhu, X. Zhang, et al., Angew. Chem. Int. Ed. 62 (2023) e202217244.
doi: 10.1002/anie.202217244
T.V. Münchow, S. Dana, Y. Xu, et al., Science 379 (2023) 1036–1042.
doi: 10.1126/science.adg2866
B. Zhang, J. He, Y. Gao, et al., Nature 623 (2023) 745–751.
doi: 10.1038/s41586-023-06677-2
J. Lu, Y. Yao, L. Li, et al., J. Am. Chem. Soc. 145 (2023) 26774–26782.
doi: 10.1021/jacs.3c08839
Y.T. Zheng, H.C. Xu, Angew. Chem. Int. Ed. 63 (2024) e202313273.
doi: 10.1002/anie.202313273
C. Huang, Y. Tao, X. Cao, et al., J. Am. Chem. Soc. 146 (2024) 1984–1991.
doi: 10.1021/jacs.3c10194
L. Zhang, M. Li, Y. Yang, et al., Green Chem. 26 (2024) 2059–2066.
doi: 10.1039/d3gc03832g
A. Shi, Y. Liu, R. Zhang, et al., eScience 4 (2024) 100255.
doi: 10.1016/j.esci.2024.100255
L. Li, X. Wang, N. Fu, Angew. Chem. Int. Ed. 63 (2024) e202403475.
doi: 10.1002/anie.202403475
J. Sheng, J. Cheng, X. Cheng, Tetrahedron Chem. 10 (2024) 100074.
doi: 10.1016/j.tchem.2024.100074
G. Kou, P. Li, G. Yang, et al., CCS Chem. 7 (2025) 3005–3014.
doi: 10.31635/ccschem.024.202404697
Y. Li, Y. Peng, W. Dong, et al., J. Am. Chem. Soc. 146 (2024) 14194–14202.
doi: 10.1021/jacs.4c03218
Y. Cao, J. Chen, C. Ding, et al., Chem. Catal. 4 (2024) 101158.
J. Xiang, M. Shang, Y. Kawamata, et al., Nature 573 (2019) 398–402.
doi: 10.1038/s41586-019-1539-y
H. Liang, L.J. Wang, Y.X. Ji, et al., Angew. Chem. Int. Ed. 60 (2020) 1839–1844.
Y. You, W. Kanna, H. Takano, et al., J. Am. Chem. Soc. 144 (2022) 3685–3695.
doi: 10.1021/jacs.1c13032
X. Cheng, A. Lei, T.S. Mei, et al., CCS Chem. 4 (2022) 1120–1152.
doi: 10.31635/ccschem.021.202101451
C.J. Long, H. Cao, B.K. Zhao, et al., Angew. Chem. Int. Ed. 61 (2022) e202203666.
doi: 10.1002/anie.202203666
X. Wang, S. Wu, Y. Zhong, et al., Chin. Chem. Lett. 34 (2023) 107537.
doi: 10.1016/j.cclet.2022.05.051
Y. Liu, Y. Sun, Y. Deng, et al., Angew. Chem. Int. Ed. 64 (2025) e202504459.
doi: 10.1002/anie.202504459
S.H. Park, G. Bae, A. Choi, et al., J. Am. Chem. Soc. 145 (2023) 15360–15369.
doi: 10.1021/jacs.3c03172
L. Zeng, J. Wang, D. Wang, et al., Angew. Chem. Int. Ed. 62 (2023) e202309620.
doi: 10.1002/anie.202309620
S. Fang, K. Zhong, S. Zeng, et al., Chem. Commun. 59 (2023) 11425–11428.
doi: 10.1039/d3cc02852f
C. Feng, X. Liu, Y. She, et al., Chin. Chem. Lett. 34 (2023) 107935.
doi: 10.1016/j.cclet.2022.107935
W. Zeng, Y. Wang, C. Peng, et al., Chem. Soc. Rev. 54 (2025) 4468–4501.
doi: 10.1039/d4cs01142b
P. Li, Z. Zhu, C. Guo, et al., Nat. Catal. 7 (2024) 412–421.
doi: 10.1038/s41929-024-01118-3
M. Liu, Y. Wang, C. Gao, et al., Angew. Chem. Int. Ed. 64 (2025) e202425634.
doi: 10.1002/anie.202425634
Y. Li, J. Xu, J.C.A. Oliveira, et al., ACS Catal. 14 (2024) 8160–8167.
doi: 10.1021/acscatal.4c01886
Q. Hu, B. Wei, M. Wang, et al., J. Am. Chem. Soc. 146 (2024) 14864–14874.
doi: 10.1021/jacs.4c04211
X. Fang, Y. Zeng, Y. Huang, et al., Nat. Commun. 15 (2024) 5181.
doi: 10.1038/s41467-024-49223-y
H. Li, Y. Li, J. Chen, et al., Angew. Chem. Int. Ed. 63 (2024) e202407392.
doi: 10.1002/anie.202407392
B.L. Chen, H.W. Zhu, Y. Xiao, et al., Electrochem. Commun. 42 (2014) 55–59.
doi: 10.1016/j.elecom.2014.02.009
H.P. Yang, Y.N. Yue, Q.L. Sun, et al., Chem. Commun. 51 (2015) 12216–12219.
doi: 10.1039/C5CC04554A
D.T. Yang, M. Zhu, Z.J. Schiffer, et al., ACS Catal. 9 (2019) 4699–4705.
doi: 10.1021/acscatal.9b00818
S. Bazzi, E. Schulz, M. Mellah, Org. Lett. 21 (2019) 10033–10037.
doi: 10.1021/acs.orglett.9b03927
L. Muchez, D.E.D. Vos, M. Kim, ACS Sustainable Chem. Eng. 7 (2019) 15860–15864.
doi: 10.1021/acssuschemeng.9b04612
H. Senboku, K. Yoneda, S. Hara, Tetrahedron Lett. 56 (2015) 6772–6776.
doi: 10.1016/j.tetlet.2015.10.068
N. Sauermann, T.H. Meyer, Y. Qiu, et al., ACS Catal. 8 (2018) 7086–7103.
doi: 10.1021/acscatal.8b01682
Y. Zhang, T. Zhang, S. Das, Chem 8 (2022) 3175–3201.
doi: 10.1016/j.chempr.2022.10.005
J.A. Ma, Angew. Chem. Int. Ed. 42 (2003) 4290–4299.
doi: 10.1002/anie.200301600
G. Li, Y. Liang, J.C. Antilla, J. Am. Chem. Soc. 129 (2007) 5830–5831.
doi: 10.1021/ja070519w
A.M. Fournier, R.A. Brown, W. Farnaby, et al., Org. Lett. 12 (2010) 2222–2225.
doi: 10.1021/ol100627c
Y. Qu, C. Tsuneishi, H. Tateno, et al., React. Chem. Eng. 2 (2017) 871–875.
doi: 10.1039/C7RE00149E
Y. Naito, Y. Nakamura, N. Shida, et al., J. Org. Chem. 86 (2021) 15953–15960.
doi: 10.1021/acs.joc.1c00821
K. Zhang, X.F. Liu, W.Z. Zhang, et al., Org. Lett. 24 (2022) 3565–3569.
doi: 10.1021/acs.orglett.2c01267
A. Dmitrieva, J.J. Medvedev, X.V. Medvedeva, et al., J. Electrochem. Soc. 170 (2023) 075501.
doi: 10.1149/1945-7111/ace0dc
H. Seo, M.H. Katcher, T.F. Jamison, Nat. Chem. 9 (2017) 453–456.
doi: 10.1038/nchem.2690
Y. Wang, S. Tang, G. Yang, et al., Angew. Chem. Int. Ed. 61 (2022) e202207746.
doi: 10.1002/anie.202207746
Y. Wang, Z. Zhao, D. Pan, et al., Angew. Chem. Int. Ed. 61 (2022) e202210201.
doi: 10.1002/anie.202210201
Z. Zhao, Y. Liu, S. Wang, et al., Angew. Chem. Int. Ed. 62 (2023) e202214710.
doi: 10.1002/anie.202214710
W. Zeng, C. Peng, Y. Qiu, J. Am. Chem. Soc. 147 (2025) 13461–13470.
doi: 10.1021/jacs.5c00259
N. Fu, L. Li, Q. Yang, et al., Org. Lett. 19 (2017) 2122–2125.
doi: 10.1021/acs.orglett.7b00746
P.S. Gao, X.J. Wang, Z.H. Wang, et al., Angew. Chem. Int. Ed. 59 (2020) 15254–15259.
doi: 10.1002/anie.202005099
Z.H. Wang, P.S. Gao, X. Wang, et al., J. Am. Chem. Soc. 143 (2021) 15599–15605.
doi: 10.1021/jacs.1c08671
O.R. Luca, T. Wang, S.J. Konezny, et al., New J. Chem. 35 (2011) 998–999.
doi: 10.1039/c0nj01011a
K.J. Jiao, Y.K. Xing, Q.L. Yang, et al., Acc. Chem. Res. 53 (2020) 300–310.
doi: 10.1021/acs.accounts.9b00603
Yongheng Ren , Yang Chen , Hongwei Chen , Lu Zhang , Jiangfeng Yang , Qi Shi , Lin-Bing Sun , Jinping Li , Libo Li . Electrostatically driven kinetic Inverse CO2/C2H2 separation in LTA-type zeolites. Chinese Journal of Structural Chemistry, 2024, 43(10): 100394-100394. doi: 10.1016/j.cjsc.2024.100394
Daheng Wen , Weiwei Fang , Yongmei Liu , Tao Tu . Valorization of carbon dioxide with alcohols. Chinese Chemical Letters, 2024, 35(7): 109394-. doi: 10.1016/j.cclet.2023.109394
Tian-Yu Gao , Xiao-Yan Mo , Shu-Rong Zhang , Yuan-Xu Jiang , Shu-Ping Luo , Jian-Heng Ye , Da-Gang Yu . Visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO2. Chinese Chemical Letters, 2024, 35(7): 109364-. doi: 10.1016/j.cclet.2023.109364
Li Li , Zhi-Xin Yan , Chuan-Kun Ran , Yi Liu , Shuo Zhang , Tian-Yu Gao , Long-Fei Dai , Li-Li Liao , Jian-Heng Ye , Da-Gang Yu . Electro-reductive carboxylation of CCl bonds in unactivated alkyl chlorides and polyvinyl chloride with CO2. Chinese Chemical Letters, 2024, 35(12): 110104-. doi: 10.1016/j.cclet.2024.110104
Xinyu Liu , Jialin Yang , Zonglin He , Jiaoyan Ai , Lina Song , Baohua Liu . Linear polyurethanes with excellent comprehensive properties from poly(ethylene carbonate) diol. Chinese Chemical Letters, 2025, 36(1): 110236-. doi: 10.1016/j.cclet.2024.110236
Yi Liu , Zhe-Hao Wang , Guan-Hua Xue , Lin Chen , Li-Hua Yuan , Yi-Wen Li , Da-Gang Yu , Jian-Heng Ye . Photocatalytic dicarboxylation of strained C–C bonds with CO2 via consecutive visible-light-induced electron transfer. Chinese Chemical Letters, 2024, 35(6): 109138-. doi: 10.1016/j.cclet.2023.109138
He Yao , Wenhao Ji , Yi Feng , Chunbo Qian , Chengguang Yue , Yue Wang , Shouying Huang , Mei-Yan Wang , Xinbin Ma . Copper-catalyzed and biphosphine ligand controlled 3,4-boracarboxylation of 1,3-dienes with carbon dioxide. Chinese Chemical Letters, 2025, 36(4): 110076-. doi: 10.1016/j.cclet.2024.110076
Zhen Zhang , Xue-ling Chen , Xiu-Mei Xie , Tian-Yu Gao , Jing Qin , Jun-Jie Li , Chao Feng , Da-Gang Yu . Iron-promoted carbonylation–rearrangement of α-aminoaryl-tethered alkylidenecyclopropanes with CO2: Facile synthesis of quinolinofurans. Chinese Chemical Letters, 2025, 36(4): 110056-. doi: 10.1016/j.cclet.2024.110056
Hao Sun , Xiaoxue Li , Baoyu Wu , Kai Zhu , Yinyi Gao , Tianzeng Bao , Hongbin Wu , Dianxue Cao . Direct regeneration of spent LiFePO4 cathode material via a simple solid-phase method. Chinese Chemical Letters, 2025, 36(6): 110041-. doi: 10.1016/j.cclet.2024.110041
Zhi-Xin Li , Xiao-Feng Qiu , Pei-Qin Liao . Efficient electroreduction of CO2 to acetate with relative purity of 100% by ultrasmall Cu2O nanoparticle on a conductive metal-organic framework. Chinese Chemical Letters, 2025, 36(11): 110473-. doi: 10.1016/j.cclet.2024.110473
Yuqing Zhong , Mengmeng Jiang , Deyong Yang , Nan Feng , Ying Sun , Huimin Wang , Feng Zhou . Nickel-catalyzed electrochemical carboxylation of propargylic esters with CO2 to 2,3-allenoic acids. Chinese Chemical Letters, 2025, 36(12): 111169-. doi: 10.1016/j.cclet.2025.111169
Yan-Cui Wen , Jia-Cheng Hou , Qian Zhou , Sheng-Hua Wang , Jun Jiang , Zi Yang , Hai-Tao Zhu , Zu-Li Wang , Wei-Min He . Linear paired electrolysis enables redox-neutral benzylation of N-heteroarenes with benzyl halides using ion resin as the recyclable electrolyte. Chinese Chemical Letters, 2025, 36(12): 111795-. doi: 10.1016/j.cclet.2025.111795
Xinyu Wu , Jianfeng Lu , Zihao Zhu , Suijun Liu , Herui Wen . Recent advances of metal-organic frameworks and MOF-derived materials based on p-block metal for the electrochemical reduction of carbon dioxide. Chinese Chemical Letters, 2025, 36(7): 110151-. doi: 10.1016/j.cclet.2024.110151
Yue Zhang , Xiaoya Fan , Xun He , Tingyu Yan , Yongchao Yao , Dongdong Zheng , Jingxiang Zhao , Qinghai Cai , Qian Liu , Luming Li , Wei Chu , Shengjun Sun , Xuping Sun . Ambient electrosynthesis of urea from carbon dioxide and nitrate over Mo2C nanosheet. Chinese Chemical Letters, 2024, 35(8): 109806-. doi: 10.1016/j.cclet.2024.109806
Yanhui Guo , Li Wei , Zhonglin Wen , Chaorong Qi , Huanfeng Jiang . Recent Progress on Conversion of Carbon Dioxide into Carbamates. Acta Physico-Chimica Sinica, 2024, 40(4): 2307004-0. doi: 10.3866/PKU.WHXB202307004
Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
Zixuan Zhao , Miao Fan . “Carbon” with No “Ester”: A Boundless Journey of CO2 Transformation. University Chemistry, 2025, 40(7): 213-217. doi: 10.12461/PKU.DXHX202409040
Xiting Zhou , Zhipeng Han , Xinlei Zhang , Shixuan Zhu , Cheng Che , Liang Xu , Zhenyu Sun , Leiduan Hao , Zhiyu Yang . Dual Modulation via Ag-Doped CuO Catalyst and Iodide-Containing Electrolyte for Enhanced Electrocatalytic CO2 Reduction to Multi-Carbon Products: A Comprehensive Chemistry Experiment. University Chemistry, 2025, 40(7): 336-344. doi: 10.12461/PKU.DXHX202412070
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Zhen Dai , Linzhi Tan , Yeyu Su , Kerui Zhao , Yushun Tian , Yu Liu , Tao Liu . Site-specific incorporation of reduction-controlled guest amino acids into proteins for cucurbituril recognition. Chinese Chemical Letters, 2024, 35(5): 109121-. doi: 10.1016/j.cclet.2023.109121