Cobalt-catalyzed regiodivergent hydroalkenylation of alkenes
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* Corresponding authors.
E-mail addresses: feipan@sicnu.edu.cn (F. Pan), linxing.zhang@hubu.edu.cn (L. Zhang), yef@ccnu.edu.cn (F. Ye).
Citation:
Jianyi Shi, Chengyi Peng, Jiali Qiu, Shuanglong Li, Wenyan Zhao, Xiang Sun, Shikai Xiang, Yandong Wu, Wenhan Xu, Fei Pan, Linxing Zhang, Fei Ye. Cobalt-catalyzed regiodivergent hydroalkenylation of alkenes[J]. Chinese Chemical Letters,
;2026, 37(9): 112824.
doi:
10.1016/j.cclet.2026.112824
B. Fu, Y. Zhao, X.P. Yuan, et al., Chin. Chem. Lett. 35 (2024) 108372.
doi: 10.1016/j.cclet.2023.108372
T.V. RajanBabu, Chem. Rev. 103 (2003) 2845–2860.
doi: 10.1021/cr020040g
J. Zhou, L.P. Hu, R. Wang, et al., Chin. Chem. Lett. 37 (2026) 111304.
doi: 10.1016/j.cclet.2025.111304
M. Hirano, ACS Catal. 9 (2019) 1408–1430.
doi: 10.1021/acscatal.8b04676
Y.L. Liu, D. Xu, Y.Y. Ping, et al., Chin. Chem. Lett. 37 (2026) 111893.
doi: 10.1016/j.cclet.2025.111893
R.H. Liu, J.S. Chen, N. Zhou, et al., Chin. Chem. Lett. 37 (2026) 112156.
doi: 10.1016/j.cclet.2025.112156
D.P. Wang, J. Dong, W.J. Fan, et al., Angew. Chem. Int. Ed. 59 (2020) 8430–8434.
doi: 10.1002/anie.201916305
A.W. Schuppe, J.L. Knippel, J. Am. Chem. Soc. 143 (2021) 5330–5335.
doi: 10.1021/jacs.1c02117
J.D. Liu, H.G. Gong, S.L. Zhu, Angew. Chem. Int. Ed. 60 (2021) 4060–4064.
doi: 10.1002/anie.202012614
L.H. Xiong, L. Chen, Z.T. He, Chin. Chem. Lett. 37 (2026) 111921.
doi: 10.1016/j.cclet.2025.111921
B.C. Wang, J.J. Zhao, J.L. Ying, et al., Angew. Chem. Int. Ed. 64 (2025) e202421500.
doi: 10.1002/anie.202421500
C.Y. Zhao, C. Dong, W.X. Ma, et al., ACS Catal. 14 (2024) 14475–14485.
doi: 10.1021/acscatal.4c03917
C.Y. Zhao, Y. Li, Y.J. Dong, et al., Nat. Commun. 13 (2022) 6297.
doi: 10.1038/s41467-022-33996-1
B. Yang, X. Ren, X.Z. Shen, et al., Chin. J. Chem. 36 (2018) 1017–1023.
doi: 10.1002/cjoc.201800320
Z.Q. Li, O. Apolinar, R.H. Deng, et al., Chem. Sci. 12 (2021) 11038–11044.
doi: 10.1039/D1SC03121J
D.M. Wang, L.Q. She, Y.C. Wu, et al., Nat. Commun. 13 (2022) 6878.
doi: 10.1038/s41467-022-34675-x
Y.M. Du, J.N. Lin, Y.L. Li, et al., J. Am. Chem. Soc. 147 (2025) 18944–18952.
doi: 10.1021/jacs.5c03451
M. Gu, Y.J. Cao, Q.Q. Zhao, et al., Chin. J. Chem. 44 (2026) 171–176.
doi: 10.1002/cjoc.70285
C.Y. Ho, L. He, Angew. Chem. Int. Ed. 49 (2010) 9182–9186.
doi: 10.1002/anie.201001849
X. Hong, J.L. Wang, Y.F. Yang, et al., ACS Catal. 5 (2015) 5545–5555.
doi: 10.1021/acscatal.5b01075
G. Hilt, ChemCatChem 7 (2015) 1639–1641.
doi: 10.1002/cctc.201500177
X. Sun, E.Z. Lin, B.J. Li, J. Am. Chem. Soc. 144 (2022) 17351–17358.
doi: 10.1021/jacs.2c07477
J. Dai, J.L. Wu, G.L. Zhao, et al., Chem. Eur. J. 17 (2011) 8290–8293.
doi: 10.1002/chem.201101190
N. Mameda, S. Peraka, S. Kodumuri, et al., RSC Adv. 6 (2016) 1296–1300.
doi: 10.1039/C5RA24948A
M. Liu, J. Zhang, H. Zhou, et al., RSC Adv. 6 (2016) 76780–76784.
doi: 10.1039/C6RA16627J
S. Fehn, S. Schwarz, R. Kempe, ChemistrySelect 2 (2017) 3289–3292.
doi: 10.1002/slct.201700595
P. Liu, H.S. Wang, Y.M. Pan, et al., Chem. Commun. 49 (2013) 5295–5297.
doi: 10.1039/c3cc41742e
S. Ogoshi, T. Haba, M. Ohashi, J. Am. Chem. Soc. 131 (2009) 10350–10351.
doi: 10.1021/ja903510u
T. Alderson, E.L. Jenner, R.V. Lindsey, J. Am. Chem. Soc. 87 (1965) 5638–5645.
doi: 10.1021/ja00952a022
G.M. DiRenzo, P.S. White, M. Brookhart, J. Am. Chem. Soc. 118 (1996) 6225–6234.
doi: 10.1021/ja9602354
M. Hirano, Y. Sakate, N. Komine, et al., Organometallics 28 (2009) 4902–4905.
doi: 10.1021/om9004065
P.K. Maity, J.A. Tunge, ChemCatChem 10 (2018) 3419–3423.
doi: 10.1002/cctc.201800525
S.H. Chen, Z.C. Han, H.S. Hu, et al., Org. Chem. Front. 12 (2025) 2011–2017.
doi: 10.1039/D4QO02344G
A.T. Biju, M. Padmanaban, N.E. Wurz, et al., Angew. Chem. Int. Ed. 50 (2011) 8412–8415.
doi: 10.1002/anie.201103555
S.I. Matsuoka, Y. Ota, A. Washio, et al., Org. Lett. 13 (2011) 3722–3725.
doi: 10.1021/ol201380m
S. Sarkar, S. Ghosh, D. Kurandina, et al., J. Am. Chem. Soc. 145 (2023) 12224–12232.
doi: 10.1021/jacs.3c02410
L.J. Li, Y.L. He, Y.H. Yang, et al., CCS Chem. 6 (2024) 537–584.
doi: 10.31635/ccschem.023.202303412
J.H. Chen, J. Guo, Z. Lu, Chin. J. Chem. 36 (2018) 1075–1109.
doi: 10.1002/cjoc.201800314
J.Y. Shi, Z.H. Dong, J.L. Qiu, et al., J. Am. Chem. Soc. 148 (2026) 13414–13425.
doi: 10.1021/jacs.6c02505
T. Michiyuki, K. Komeyama, Asian J. Org. Chem. 9 (2020) 343–358.
doi: 10.1002/ajoc.201900625
B. Zhang, T.T. Li, Z.C. Mao, et al., J. Am. Chem. Soc. 146 (2024) 1410–1422.
doi: 10.1021/jacs.3c10439
H. Huang, J.H. Ye, L. Zhu, et al., CCS Chem. 2 (2020) 1746–1756.
J.C. Xu, J.P. Yue, M. Pan, et al., Nat. Commun. 16 (2025) 1850.
doi: 10.1038/s41467-025-57060-w
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
W. Zhou, I.A. Dmitriev, P. Melchiorre, J. Am. Chem. Soc. 145 (2023) 25098–25102.
doi: 10.1021/jacs.3c11285
H. Lindner, W.M. Amberg, T. Martini, et al., Angew. Chem. Int. Ed. 63 (2024) e202319515.
doi: 10.1002/anie.202319515
I. Fernández, F.M. Bickelhaupt, Chem. Soc. Rev. 43 (2014) 4953–4967.
doi: 10.1039/C4CS00055B
F.M. Bickelhaupt, K.N. Houk, Angew. Chem. Int. Ed. 56 (2017) 10070–10086.
doi: 10.1002/anie.201701486
C.C. Wang, P.S. Lin, C.H. Cheng, Tetrahedron Lett. 45 (2004) 6203–6206.
doi: 10.1016/j.tetlet.2004.04.085
M.E. Weiss, L.M. Kreis, A. Lauber, et al., Angew. Chem. Int. Ed. 50 (2011) 11125–11128.
doi: 10.1002/anie.201105235
G.N. Schrauzer, R.J. Windgassen, J. Am. Chem. Soc. 89 (1967) 1999–2007.
doi: 10.1021/ja00985a006
P. Maillard, C. Cianotti, Can. J. Chem. 60 (1982) 1402–1413.
doi: 10.1139/v82-205
M. Ociepa, A.J. Wierzba, J. Turkowska, et al., J. Am. Chem. Soc. 142 (2020) 5355–5361.
doi: 10.1021/jacs.0c00245
X. Sun, J.T. Chen, T. Ritter, Nat. Chem. 10 (2018) 1229–1233.
doi: 10.1038/s41557-018-0142-4
H. Cao, H.M. Jiang, H.Y. Feng, et al., J. Am. Chem. Soc. 140 (2018) 16360–16367.
doi: 10.1021/jacs.8b11218
W. Zhao, S. Wu, P. Melchiorre, et al., J. Am. Chem. Soc. 144 (2022) 8914– 8919.
doi: 10.1021/jacs.2c03546
S.C. Wang, D.M. Ren, Z. Liu, et al., Nat. Synth. 2 (2023) 1202–1210.
doi: 10.1038/s44160-023-00365-9
T. Qin, G.W. Lv, Q. Meng, et al., Angew. Chem. Int. Ed. 60 (2021) 25949–25957.
doi: 10.1002/anie.202110178
T. Qin, G.W. Lv, H.R. Miao, et al., Angew. Chem. Int. Ed. 61 (2022) e202201967.
doi: 10.1002/anie.202201967
H.R. Miao, M.H. Guan, T. Xiong, et al., Angew. Chem. Int. Ed. 62 (2023) e202213913.
doi: 10.1002/anie.202213913
Y.N. Yin, B.S. Zhao, H.Y. Liu, et al., Chem 10 (2024) 3088–3099.
doi: 10.1016/j.chempr.2024.05.021
Zhen-Qi Wang , Lin-Wen Wei , Zhao-Qing Wang , Yan-Jie Yang , Yu Zhao , Song Liu , Yuan Huang . Modular synthesis of polyfunctionalized axial-chiral 2-arylpyridines via cobalt-catalyzed asymmetric [2 + 2 + 2] cycloaddition of diynes and nitriles. Chinese Chemical Letters, 2026, 37(4): 111377-. doi: 10.1016/j.cclet.2025.111377
Hongping Zhao , Weiming Yuan . Merging catalytic electron donor-acceptor complex and copper catalysis: Enantioselective radical carbocyanation of alkenes. Chinese Chemical Letters, 2025, 36(10): 110894-. doi: 10.1016/j.cclet.2025.110894
Zhihua Wang , Xiang-Zhao Zhu , Xinglei He , Chen-Xu Gong , Wang-Fu Liang , Wenfeng Wang , Yuqi Lin , Ke-Yin Ye . Deoxygenative hydrohalogenation of propargyl alcohols: Regio- and stereoselective synthesis of unsaturated distal dihalides. Chinese Chemical Letters, 2025, 36(12): 111067-. doi: 10.1016/j.cclet.2025.111067
Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp3)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
Minghui Zhang , Na Zhang , Qian Zhao , Chao Wang , Alexander Steiner , Jianliang Xiao , Weijun Tang . Cobalt pincer complex-catalyzed highly enantioselective hydrogenation of quinoxalines. Chinese Chemical Letters, 2025, 36(4): 110081-. doi: 10.1016/j.cclet.2024.110081
Zhenkang Ai , Hui Chen , Xuebin Liao . Nickel-catalyzed decarboxylative difluoromethylation and alkylation of alkenes. Chinese Chemical Letters, 2025, 36(3): 109954-. doi: 10.1016/j.cclet.2024.109954
Er-Meng Wang , Ziyi Wang , Xu Ban , Xiaowei Zhao , Yanli Yin , Zhiyong Jiang . Chemoselective photocatalytic sulfenylamination of alkenes with sulfenamides via energy transfer. Chinese Chemical Letters, 2024, 35(12): 109843-. doi: 10.1016/j.cclet.2024.109843
Wenyan Zhao , Tiantian Liang , Dongcheng Zheng , Jiali Qiu , Juan Zheng , Yandong Wu , Wenhan Xu , Liang Liu , Fei Ye . Nickel-catalyzed quantitative deuterated reduction of quinolines and alkenes. Chinese Chemical Letters, 2026, 37(8): 112035-. doi: 10.1016/j.cclet.2025.112035
Fan Chen , Xiaoyu Zhao , Weihang Miao , Yingying Li , Ye Yuan , Lingling Chu . Regio- and enantioselective hydrofluorination of internal alkenes via nickel-catalyzed hydrogen atom transfer. Chinese Chemical Letters, 2025, 36(5): 110239-. doi: 10.1016/j.cclet.2024.110239
Luyun Zhang , Ding Liu , Huri Piao , Zhenhua Jia , Fen-Er Chen . A modified Bis-OPNN phosphorus ligand for Rh-catalyzed linear-selective hydroformylation of alkenes. Chinese Chemical Letters, 2025, 36(7): 110640-. doi: 10.1016/j.cclet.2024.110640
Yaqi Deng , Jian Xue , Xiang Wu , Shunying Liu . Highly regioselective electrochemical oxidative 2,1-azolization of alkenes with azoles and nucleophiles. Chinese Chemical Letters, 2025, 36(9): 110822-. doi: 10.1016/j.cclet.2025.110822
Ruihua Liu , Jiashu Chen , Nan Zhou , Cong Shi , Hongyun Qin , Wenlong Shan , Zemin Wang , Chenxia Gao , Chao Liu , Bokan Wang , Chao Xie , Xiangqian Li , Yuxi Lin , Jiqiang Zhu , Pan Xing , Dayong Shi . Dual photocatalytic access to antiviral alkenyl phosphonates via radical 1,4-difunctionalization across ordinary alkenes and arylacetylenes. Chinese Chemical Letters, 2026, 37(8): 112156-. doi: 10.1016/j.cclet.2025.112156
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
Heng Yang , Zhijie Zhou , Conghui Tang , Feng Chen . Recent advances in heterogeneous hydrosilylation of unsaturated carbon-carbon bonds. Chinese Chemical Letters, 2024, 35(6): 109257-. doi: 10.1016/j.cclet.2023.109257
Zhiqian Chang , Xiaochun He , Xuemei Zhang , Zhong Lian . Stereoconvergent synthesis of chiral sulfonyl phthalide containing two chiral centers from Z/E mixed alkenes via copper catalysis. Chinese Chemical Letters, 2026, 37(5): 111405-. doi: 10.1016/j.cclet.2025.111405
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. Chinese Chemical Letters, 2026, 37(4): 111304-. doi: 10.1016/j.cclet.2025.111304
Yongli Liu , Dan Xu , Yuanyuan Ping , Nengzhong Wang , Wangqing Kong . Enantioselective synthesis of α-aryl ketones via cross-hydroacylation of two distinct alkenes. Chinese Chemical Letters, 2026, 37(3): 111893-. doi: 10.1016/j.cclet.2025.111893
Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
Haitao Liu , Youlin Deng , Dan Ling , Lingzhu Chen , Zhichao Jin . Asymmetric catalysis for the synthesis of planar chiral ferrocene derivatives. Chinese Chemical Letters, 2026, 37(3): 111793-. doi: 10.1016/j.cclet.2025.111793
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