Three-component alkenylcarboxylation of two distinct alkenes with CO2 via photoinduced palladium catalysis
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* Corresponding authors.
E-mail addresses: junxu@hfut.edu.cn (J. Xu), hjxu@hfut.edu.cn (H. Xu).
Citation:
Jie Zhou, Luping Hu, Rui Wang, Ruijie Wang, Jun Xu, Huajian Xu. Three-component alkenylcarboxylation of two distinct alkenes with CO2 via photoinduced palladium catalysis[J]. Chinese Chemical Letters,
;2026, 37(4): 111304.
doi:
10.1016/j.cclet.2025.111304
S.H. Cho, J.Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 40 (2011) 5068–5083.
doi: 10.1039/c1cs15082k
C.J. Li, Acc. Chem. Res. 42 (2009) 335–344.
doi: 10.1021/ar800164n
T. Koike, M. Akita, Org. Chem. Front. 3 (2016) 1345–1349.
doi: 10.1039/C6QO00139D
G. Yin, X. Mu, G.S. Liu, Acc. Chem. Res. 49 (2016) 2413–2423.
doi: 10.1021/acs.accounts.6b00328
W. Ge, J.X. Wang, M.C. Fu, Y. Fu, Chin. J. Chem. (2024) 1203–120842.
doi: 10.1002/cjoc.202300740
A.H. Hoveyda, A.R. Zhugralin, Nature 450 (2007) 243–251.
doi: 10.1038/nature06351
O.M. Ogba, N.C. Warner, D.J. O’Leary, R.H. Grubbs, Chem. Soc. Rev. 47 (2018) 4510–4544.
doi: 10.1039/c8cs00027a
C.Y. Ho, C.W. Chan, L. He, Angew. Chem. Int. Ed. 54 (2015) 4512–4516.
doi: 10.1002/anie.201411882
T.V. RajanBabu, Chem. Rev. 103 (2003) 2845–2860.
doi: 10.1021/cr020040g
S. Sarkar, S. Ghosh, D. Kurandina, Y. Noffel, V. Gevorgyan, J. Am. Chem. Soc. 145 (2023) 12224–12232.
doi: 10.1021/jacs.3c02410
Z.K. Wen, Y.H. Xu, T.P. Loh, Chem. Sci. 4 (2013) 4520–4524.
doi: 10.1039/c3sc52275j
Q.J. Liang, C. Yang, F.F. Meng, et al., Angew. Chem. Int. Ed. 56 (2017) 5091–5095.
doi: 10.1002/anie.201700559
B. Jiang, M. Zhao, S.S. Li, Y.H. Xu, T.P. Loh, Angew. Chem. Int. Ed. 57 (2018) 555–559.
doi: 10.1002/anie.201710601
K. Meng, Y. Sun, J. Zhang, et al., Org. Lett. 21 (2019) 8219–8224.
doi: 10.1021/acs.orglett.9b02935
J.C. Lo, J. Gui, Y. Yabe, C.M. Pan, P.S. Baran, Nature 516 (2014) 343–348.
doi: 10.1038/nature14006
J. Streuff, Chem. Eur. J. 17 (2011) 5507–5510.
doi: 10.1002/chem.201100501
M. Kong, Y. Tan, X. Zhao, et al., J. Am. Chem. Soc. 143 (2021) 4024–4031.
doi: 10.1021/jacs.1c01073
Z.G. Wu, M.Y. Wu, K. Zhu, J. Wu, Y.X. Lu, Chem 9 (2023) 978–988.
doi: 10.1016/j.chempr.2022.12.013
B.H. Rotstein, S. Zaretsky, V. Rai, A.K. Yudin, Chem. Rev. 114 (2014) 8323–8359.
doi: 10.1021/cr400615v
A. Dömling, W. Wang, K. Wang, Chem. Rev. 112 (2012) 3083–3135.
doi: 10.1021/cr100233r
G. Tan, F. Paulus, A. Petti, et al., Chem. Sci. 14 (2023) 2447–2454.
doi: 10.1039/d2sc06497a
F. Paulus, C. Stein, C. Heusel, et al., J. Am. Chem. Soc. 145 (2023) 23814–23823.
doi: 10.1021/jacs.3c08898
D. Wu, W. Kong, Y. Bao, et al., Nat. Catal. 6 (2023) 1030–1041.
doi: 10.1038/s41929-023-01032-0
Y. Chen, J. Wu, Y. Ding, H.M. Huang, Org. Chem. Front. 12 (2025) 85–89.
doi: 10.1039/D4QO01312C
Y. Zhang, K.D. Li, C.Q. Zhou, Z.X. Xing, H.M. Huang, Green Chem. 26 (2024) 10434–10440.
doi: 10.1039/d4gc02879a
X.B. Lu, W.M. Ren, G.P. Wu, Acc. Chem. Res. 45 (2012) 1721–1735.
doi: 10.1021/ar300035z
Q. Liu, L.P. Wu, R. Beller, M. Jackstell, Nat. Commun. 6 (2015) 5933.
doi: 10.1038/ncomms6933
M.Y. He, Y.H. Sun, B.X. Han, Angew. Chem. Int. Ed. 61 (2022) e202112835.
doi: 10.1002/anie.202112835
Q.Y. Meng, S. Wang, G.S. Huff, B. König, J. Am. Chem. Soc. 140 (2018) 3198–3201.
doi: 10.1021/jacs.7b13448
H. Huang, J.H. Ye, D.G. Yu, et al., C–C S Chem. 3 (2021) 1746–1756.
doi: 10.31635/ccschem.020.202000374
Y. Jin, J. Caner, S. Nishikawa, N. Toriumi, N. Iwasawa, Nat. Commun. 13 (2022) 7584.
doi: 10.1038/s41467-022-35293-3
B. Yu, Y. Liu, H.Z. Xiao, et al., Chem 10 (2024) 938–951.
doi: 10.1016/j.chempr.2023.12.005
V.R. Yatham, Y.Y. Shen, R. Martin, Angew. Chem. Int. Ed. 56 (2017) 10915–10919.
doi: 10.1002/anie.201706263
H. Wang, Y.Z. Gao, C.L. Zhou, G. Li, J. Am. Chem. Soc. 142 (2020) 8122–8129.
doi: 10.1021/jacs.0c03144
L.L. Liao, G.M. Cao, Y.X. Jiang, et al., J. Am. Chem. Soc. 143 (2021) 2812–2821.
doi: 10.1021/jacs.0c11896
J. Hou, A. Ee, H. Cao, et al., Angew. Chem. Int. Ed. 57 (2018) 17220–17224.
doi: 10.1002/anie.201811266
J.H. Ye, M. Miao, H. Huang, et al., Angew. Chem. Int. Ed. 56 (2017) 15416–15420.
doi: 10.1002/anie.201707862
Q. Fu, Z.Y. Bo, J.H. Ye, et al., Nat. Commun. 10 (2019) 3592.
doi: 10.1038/s41467-019-11528-8
W. Zhang, Z. Chen, Y.X. Jiang, et al., Nat. Commun. 14 (2023) 3529.
doi: 10.1038/s41467-023-39240-8
T. Ju, Y.Q. Zhou, K.G. Cao, et al., Nat. Catal. 4 (2021) 304–311.
doi: 10.1038/s41929-021-00594-1
J.P. Yue, J.C. Xu, H.T. Luo, et al., Nat. Catal. 6 (2023) 959–968.
doi: 10.1038/s41929-023-01029-9
B. Zhang, T.T. Li, Z.C. Mao, et al., J. Am. Chem. Soc. 146 (2024) 1410–1422.
doi: 10.1021/jacs.3c10439
J.C. Xu, J.P. Yue, M. Pan, et al., Nat. Commun. 16 (2025) 1850.
doi: 10.1038/s41467-025-57060-w
S. Sarkar, K.P.S. Cheung, V. Gevorgyan, Angew. Chem. Int. Ed. 63 (2024) e202311972.
doi: 10.1002/anie.202311972
M. Parasram, P. Chuentragool, D. Sarkar, V. Gevorgyan, J. Am. Chem. Soc. 138 (2016) 6340–6343.
doi: 10.1021/jacs.6b01628
Y.C. Luo, F.F. Tong, Y. Zhang, C.Y. He, X.G. Zhang, J. Am. Chem. Soc. 143 (2021) 13971–13979.
doi: 10.1021/jacs.1c07459
Y. Liang, T.C. Bian, K. Yadav, et al., ACS Cent. Sci. 10 (2024) 1191–1200.
doi: 10.1021/acscentsci.4c00094
N. Oku, M. Murakami, T. Miura, Org. Lett. 24 (2022) 1616–1619.
doi: 10.1021/acs.orglett.2c00121
H. Xin, L.N. Guo, M. Yang, et al., Org. Chem. Front. 10 (2023) 1147–1152.
doi: 10.1039/d2qo02001g
J. Wang, Q.X. Zhou, L.J. Zhou, Z.X. Zhang, ACS Catal. 14 (2024) 18499–18506.
doi: 10.1021/acscatal.4c06842
K. Yamada, K.P. Cheung, V. Gevorgyan, J. Am. Chem. Soc. 146 (2024) 18218–18223.
doi: 10.1021/jacs.4c06421
N. Kvasovs, J. Fang, F. Kliuev, V. Gevorgyan, J. Am. Chem. Soc. 145 (2023) 18497–18505.
doi: 10.1021/jacs.3c04968
X.Y. Ruan, D.X. Wu, W.A. Li, et al., J. Am. Chem. Soc. 146 (2024) 12053–12062.
doi: 10.1021/jacs.4c01690
Y. Cai, G. Gaurav, T. Ritter, Angew. Chem. Int. Ed. 63 (2024) e202311250.
doi: 10.1002/anie.202311250
S. Maiti, P. Ghosh, D. Raja, et al., Nat. Catal. 7 (2024) 285–294.
doi: 10.1038/s41929-024-01109-4
P.S.K. Cheung, J. Fang, K. Mukherjee, A. Mihranyan, V. Gevorgyan, Science 378 (2022) 1207–1213.
doi: 10.1126/science.abq1274
H.H. Han, W.Q. Yi, S.J. Ding, X.Y. Ren, B.G. Zhao, Angew. Chem. Int. Ed. 64 (2025) e202418910.
doi: 10.1002/anie.202418910
Z.L. Liu, Z.P. Ye, Z.H. Liao, et al., ACS Catal. 14 (2024) 3725–3732.
doi: 10.1021/acscatal.4c00470
H. Yu, Q.L. Zhang, W.W. Zi, Angew. Chem. Int. Ed. 61 (2022) e202208411.
doi: 10.1002/anie.202208411
G.Z. Wang, R. Shang, W.M. Cheng, Y. Fu, J. Am. Chem. Soc. 139 (2017) 18307–18312.
doi: 10.1021/jacs.7b10009
W. Yao, G.Y. Zhao, Y. Wu, et al., J. Am. Chem. Soc. 144 (2022) 3353–3359.
doi: 10.1021/jacs.1c13299
D. Kurandina, M. Parasram, V. Gevorgyan, Angew. Chem. Int. Ed. 56 (2017) 14212–14216.
doi: 10.1002/anie.201706554
T.Z. Zhang, M.Q. Shen, Q. Zhang, M.C. Fu, Org. Lett. 26 (2024) 8890–8898.
doi: 10.1021/acs.orglett.4c03343
Y.J. Du, X.X. Sheng, J.H. Li, et al., Chem. Sci. 14 (2023) 3580–3586.
doi: 10.1039/d2sc06852d
P. Chuentragool, D. Yadagiri, T. Morita, et al., Angew. Chem. Int. Ed. 58 (2019) 1794–1798.
doi: 10.1002/anie.201812398
K.P.S. Cheung, D. Kurandina, T. Yata, V. Gevorgyan, J. Am. Chem. Soc. 142 (2020) 9932–9937.
doi: 10.1021/jacs.0c03993
M. Ratushnyy, N. Kvasovs, S. Sarkar, V. Gevorgyan, Angew. Chem. Int. Ed. 59 (2020) 10316–10320.
doi: 10.1002/anie.201915962
S. Yang, S.S. Cai, J.H. Li, M. Chen, J. Org. Chem. 89 (2024) 7243–7254.
doi: 10.1021/acs.joc.4c00703
W.W. Ding, Y. Zhou, S. Song, Z.Y. Han, Org. Lett. 24 (2022) 7350–7354.
doi: 10.1021/acs.orglett.2c02877
X.X. Sheng, Y.J. Du, J.H. Li, Q.Q. Teng, M. Chen, Org. Lett. 25 (2023) 3664–3669.
doi: 10.1021/acs.orglett.3c01030
W.W. Jin, S.Y. Yu, Org. Lett. 23 (2021) 6931–6935.
doi: 10.1021/acs.orglett.1c02509
Z.Y. Zhang, N. Kvasovs, A. Dubrovina, V. Gevorgyan, Angew. Chem. Int. Ed. 61 (2022) e202110924.
doi: 10.1002/anie.202110924
Z.L. Liu, J.L. Yan, K. Chen, H.Y. Xiang, H. Yang, Org. Lett. 26 (2024) 8762–8767.
doi: 10.1021/acs.orglett.4c03080
N. Kvasovs, V. Gevorgyan, Org. Lett. 24 (2022) 4176–4181.
doi: 10.1021/acs.orglett.2c01409
H.M. Huang, M. Koy, E. Serrano, et al., Nat. Catal. 3 (2020) 393–400.
doi: 10.1038/s41929-020-0434-0
K. Ⅲ. Tanaka, ACS Catal. 14 (2024) 5269–5274.
doi: 10.1021/acscatal.4c00510
M.Z. Lu, J. Goh, M. Maraswami, et al., Chem. Rev. 122 (2022) 17479–17646.
doi: 10.1021/acs.chemrev.2c00032
T.U. Sastry, K.N. Rao, T.A. Reddy, P. Gandhi, Asian J. Org. Chem. 26 (2014) 2417–2421.
doi: 10.14233/ajchem.2014.16137
C.A. Miller, L.M. Long, J. Am. Chem. Soc. 73 (1951) 4895–4898.
doi: 10.1021/ja01154a126
W. Zhou, I.A. Dmitriev, P. Melchiorre, J. Am. Chem. Soc. 145 (2023) 25098–25102.
doi: 10.1021/jacs.3c11285
C.H. Song, X.H. Bai, B. Li, Y.F. Dang, S.Y. Yu, J. Am. Chem. Soc. 146 (2024) 21137–21146.
doi: 10.1021/jacs.4c07126
C.H. Song, S.Y. Yu, ACS Catal. 14 (2024) 15997–16002.
doi: 10.1021/acscatal.4c04956
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
Zixuan Zhu , Xianjin Shi , Yongfang Rao , Yu Huang . Recent progress of MgO-based materials in CO2 adsorption and conversion: Modification methods, reaction condition, and CO2 hydrogenation. Chinese Chemical Letters, 2024, 35(5): 108954-. doi: 10.1016/j.cclet.2023.108954
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
Tianbo Jia , Lili Wang , Zhouhao Zhu , Baikang Zhu , Yingtang Zhou , Guoxing Zhu , Mingshan Zhu , Hengcong Tao . Modulating the degree of O vacancy defects to achieve selective control of electrochemical CO2 reduction products. Chinese Chemical Letters, 2024, 35(5): 108692-. doi: 10.1016/j.cclet.2023.108692
Li Li , Fanpeng Chen , Bohang Zhao , Yifu Yu . Understanding of the structural evolution of catalysts and identification of active species during CO2 conversion. Chinese Chemical Letters, 2024, 35(4): 109240-. doi: 10.1016/j.cclet.2023.109240
Lihui Ou , Zhancheng Liu , Dai-Huo Liu , Zhi Zhang . Cl-adsorbed Cu(111)/H2O interface selectively realizes electrochemical CO2 reduction towards C2H4 product: Mechanistic understanding. Chinese Chemical Letters, 2026, 37(2): 111920-. doi: 10.1016/j.cclet.2025.111920
Honghong Zhang , Zhen Wei , Derek Hao , Lin Jing , Yuxi Liu , Hongxing Dai , Weiqin Wei , Jiguang Deng . 非均相催化CO2与烃类协同催化转化的最新进展. Acta Physico-Chimica Sinica, 2025, 41(7): 100073-0. doi: 10.1016/j.actphy.2025.100073
Ping Wang , Tianbao Zhang , Zhenxing Li . Reconstruction mechanism of Cu surface in CO2 reduction process. Chinese Journal of Structural Chemistry, 2024, 43(8): 100328-100328. doi: 10.1016/j.cjsc.2024.100328
Xueyang Zhao , Bangwei Deng , Hongtao Xie , Yizhao Li , Qingqing Ye , Fan Dong . Recent process in developing advanced heterogeneous diatomic-site metal catalysts for electrochemical CO2 reduction. Chinese Chemical Letters, 2024, 35(7): 109139-. doi: 10.1016/j.cclet.2023.109139
Jiayin Hu , Yafei Guo , Long Li , Tianlong Deng . Teaching Innovation of Salt-Water System Phase Diagrams under the “Dual Carbon” Background: Introducing the Pressurized CO2 Carbonization Phase Equilibria. University Chemistry, 2025, 40(11): 31-36. doi: 10.12461/PKU.DXHX202412031
Mulin Yu , Shuo Liu , Yufeng Tang , Guoqiang Lu , Linbo Liu , Pengfei Sui , Xianzhu Fu , Subiao Liu , Yifei Sun , Jingli Luo . Mediating electron delocalization of surface palladium atoms by diethylamine ligand for efficient CO2 electroreduction. Chinese Chemical Letters, 2026, 37(3): 111958-. doi: 10.1016/j.cclet.2025.111958
Xia Jiang , Yan-Xin Chen , Rui Chen , Hao-Yan Shi , Ke-Xian Li , Wen-Ya Zhong , Jian-Feng Li , Can-Zhong Lu . Thermo-photocatalytic CO2 conversion with H2O to C2 products in a continuous process by ZIF-67/biochar composites. Chinese Chemical Letters, 2026, 37(4): 111781-. doi: 10.1016/j.cclet.2025.111781
Takuya Tanaka , Rikuto Noda , Yuki Sawatari , Riki Iwai , Ben Zhong Tang , Gen-ichi Konishi . Viscosity responsiveness of excited-state dynamics in aggregated-induced emission luminogens. Chinese Chemical Letters, 2025, 36(12): 111495-. doi: 10.1016/j.cclet.2025.111495
Yanjie Li , Chaoqun Qu , Siqi Meng , Jiaqi Hu , Ze Gao , Hongji Xu , Rui Gao , Ming Feng . Revealing electronic state evolution of Co(Ⅱ)/Co(Ⅲ) in CoO (111) plane during OER process through magnetic measurement. Chinese Chemical Letters, 2025, 36(3): 109872-. doi: 10.1016/j.cclet.2024.109872
Yuhao Guo , Na Li , Tingjiang Yan . Tandem catalysis for photoreduction of CO2 into multi-carbon fuels on atomically thin dual-metal phosphochalcogenides. Chinese Journal of Structural Chemistry, 2024, 43(7): 100320-100320. doi: 10.1016/j.cjsc.2024.100320
Pei Xu , Tian-Zi Hao , Zhi-Tao Liu , Yi-Qin Liu , Hui-Xian Jiang , Dong Guo , Xu Zhu . Visible-light-induced dual catalysis for divergent reduction of nitro compounds with CO2 radical anion. Chinese Chemical Letters, 2025, 36(10): 110899-. doi: 10.1016/j.cclet.2025.110899
Zhiwei Zhong , Yanbin Huang , Wantai Yang . A simple photochemical method for surface fluorination using perfluoroketones. Chinese Chemical Letters, 2024, 35(5): 109339-. doi: 10.1016/j.cclet.2023.109339
Mei Peng , Wei-Min He . Photochemical synthesis and group transfer reactions of azoxy compounds. Chinese Chemical Letters, 2024, 35(8): 109899-. doi: 10.1016/j.cclet.2024.109899
Shehla Khalid , Muhammad Bilal , Nasir Rasool , Muhammad Imran . Photochemical reactions as synthetic tool for pharmaceutical industries. Chinese Chemical Letters, 2024, 35(9): 109498-. doi: 10.1016/j.cclet.2024.109498
Zhao Gu , Yunhui Yang , Song Ye , Congyang Wang . 2,3-Arylacylation of allenes through synergetic catalysis of palladium and N-heterocyclic carbene. Chinese Chemical Letters, 2025, 36(5): 110334-. doi: 10.1016/j.cclet.2024.110334