Nickel-Catalyzed Allylic Defluorinative Cross-Electrophile Coupling of Trifluoromethyl-Substituted Alkenes with Alkyl Mesylates

doi:10.6023/cjoc202603041

Abstract

A nickel-catalyzed reductive system that enables an intermolecular allylic defluorinative cross-electrophile coupling between trifluoromethyl-substituted alkenes and secondary alkyl mesylates is developed. It provides a direct and efficient method for constructing gem-difluoroalkenes, using alcohol-derived substrates as electrophilic alkyl sources. The reaction proceeds via an in situ (pseudo)halide-exchange strategy, in which sodium iodide converts alkyl mesylates into highly reactive alkyl iodide species, thereby enabling their smooth participation in the subsequent catalytic cycle.

Key words: C—F bond cleavage, C—O bond cleavage, gem-difluoroalkene, cross-electrophile coupling, nickel catalysis

Cite this article

Yi Fang, Chuan Wang. Nickel-Catalyzed Allylic Defluorinative Cross-Electrophile Coupling of Trifluoromethyl-Substituted Alkenes with Alkyl Mesylates[J]. Chinese Journal of Organic Chemistry, 2026, 46(7): 2743-2750.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 4

References 14

[1]	(a) Meanwell, N. A. J. Med. Chem. 2011, 54, 2529. doi: 10.1021/jm1013693 pmid: 19530698
	(b) Bobek, M.; Kavai, I.; De Clercq, E. J. Med. Chem. 1987, 30, 1494. pmid: 19530698
	(c) Pan, Y.; Qiu, J.; Silverman, R. B. J. Med. Chem. 2003, 46, 5292. doi: 10.1021/jm034162s pmid: 19530698
	(d) Altenburger, J.-M.; Lassalle, G. Y.; Matrougui, M.; Galtier, D.; Jetha, J.-C.; Bocskei, Z.; Berry, C. N.; Lunven, C.; Lorrain, J.; Herault, J.-P.; Schaeffer, P.; O'Connor, S. E.; Herbert, J.-M. Bioorg. Med. Chem. 2004, 12, 1713. doi: 10.1016/j.bmc.2004.01.016 pmid: 19530698
	(e) Magueur, G.; Crousse, B.; Ourévitch, M.; Bonnet-Delpon, D.; Bégué, J.-P. J. Fluorine Chem. 2006, 127, 637. doi: 10.1016/j.jfluchem.2005.12.013 pmid: 19530698
	(f) Messaoudi, S.; Treguier, B.; Hamze, A.; Provot, O.; Peyrat, J.-F.; De Losada, J. R.; Liu, J.-M.; Bignon, J.; Wdzieczak-Bakala, J.; Thoret, S.; Dubois, J.; Brion, J.-D.; Alami, M. J. Med. Chem. 2009, 52, 4538. doi: 10.1021/jm900321u pmid: 19530698
[2]	(a) Chelucci, G. Chem. Rev. 2012, 112, 1344. doi: 10.1021/cr200165q pmid: 22085400
	(b) Zhang, X.; Cao, S. Tetrahedron Lett. 2017, 58, 375. doi: 10.1016/j.tetlet.2016.12.054 pmid: 22085400
[3]	(a) Tian, F.; Yan, G.; Yu, J. Chem. Commun. 2019, 55, 13486. doi: 10.1039/C9CC06465F
	(b) Fujita, T.; Fuchibe, K.; Ichikawa, J. Angew. Chem., Int. Ed. 2019, 58, 390. doi: 10.1002/anie.v58.2
	(c) Zhao, F.; Zhou, W.; Zuo, Z. Adv. Synth. Catal. 2022, 364, 234. doi: 10.1002/adsc.v364.2
	(d) Li, S.; Shu, W. Chem. Commun. 2022, 58, 1066. doi: 10.1039/D1CC06446K
	(e) Song, S.-Y.; Xu, S.-M. Chin. J. Org. Chem. 2023, 43, 411 (in Chinese).
	(宋树勇, 徐森苗, 有机化学, 2023, 43, 411.)
	(f) Jin, Y.; Ren, B.; Liang, F. Chin. J. Org. Chem. 2023, 44, 85 (in Chinese). doi: 10.6023/cjoc202307004
	(金玉坤, 任保轶, 梁福顺, 有机化学, 2024, 44, 85.) doi: 10.6023/cjoc202307004
	(g) Liu, F.; Wu, Q.; Wang, X.; Dong, Q.; Sun, K. Org. Chem. Front. 2025, 12, 3725. doi: 10.1039/D5QO00306G
[4]	(a) Faqua, S. A.; Duncan, W. G.; Silverstein, R. M. Tetrahedron Lett. 1964, 5, 1461. doi: 10.1016/S0040-4039(01)89512-5
	(b) Nowak, R.; Robins, M. J. Org. Lett. 2005, 7, 721. doi: 10.1021/ol047416s
	(c) Zhao, Y.; Huang, W.; Zhu, L.; Hu, J. Org. Lett. 2010, 12, 1444. doi: 10.1021/ol100090r
	(d) Zheng, J.; Lin, J.-H.; Cai, J.; Xiao, J.-C. Chem. Eur. J. 2013, 19, 15261. doi: 10.1002/chem.v19.45
	(e) Aikawa, K.; Toya, W.; Nakamura, Y.; Mikami, K. Org. Lett. 2015, 17, 4996. doi: 10.1021/acs.orglett.5b02439
	(f) Krishnamoorthy, S.; Kothandaraman, J.; Saldana, J.; Prakash, G. K. S. Eur. J. Org. Chem. 2016, 2016, 4965. doi: 10.1002/ejoc.v2016.29
[5]	(a) Hu, M.; He, Z.; Gao, B.; Li, L.; Ni, C.; Hu, J. J. Am. Chem. Soc. 2013, 135, 17302. doi: 10.1021/ja409941r pmid: 26636182
	(b) Zheng, J.; Lin, J.-H.; Yu, L.-Y.; Wei, Y.; Zheng, X.; Xiao, J.-C. Org. Lett. 2015, 17, 6150. doi: 10.1021/acs.orglett.5b03159 pmid: 26636182
	(c) Zhang, Z.; Yu, W.; Wu, C.; Wang, C.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2016, 55, 273. doi: 10.1002/anie.v55.1 pmid: 26636182
[6]	(a) Nenajdenko, V. G.; Varseev, G. N.; Korotchenko, V. N.; Shastin, A. V.; Balenkova, E. S. J. Fluorine Chem. 2003, 124, 115. doi: 10.1016/S0022-1139(03)00199-4
	(b) Wang, S.; Cheng, B.-Y.; Sršen, M.; König, B. J. Am. Chem. Soc. 2020, 142, 7524. doi: 10.1021/jacs.0c00629
[7]	(a) Kendrick, D. A.; Kolb, M. J. Fluorine Chem. 1989, 45, 265. doi: 10.1016/S0022-1139(00)84151-2 pmid: 31245895
	(b) Bégué, J.-P.; Bonnet-Delpon, D.; Rock, M. H. Tetrahedron Lett. 1995, 36, 5003. pmid: 31245895
	(c) Fuchikami, T.; Shibata, Y.; Suzuki, Y. Tetrahedron Lett. 1986, 27, 3173. doi: 10.1016/S0040-4039(00)84746-2 pmid: 31245895
	(d) Fujita, M.; Obayashi, M.; Hiyama, T. Tetrahedron 1988, 44, 4135. doi: 10.1016/S0040-4020(01)86661-8 pmid: 31245895
	(e) Fuchibe, K.; Takahashi, M.; Ichikawa, J. Angew. Chem., Int. Ed. 2012, 51, 12059. doi: 10.1002/anie.v51.48 pmid: 31245895
	(f) Coates, G.; Tan, H. Y.; Kalff, C.; White, A. J. P.; Crimmin, M. R. Angew. Chem. Int. Ed. 2019, 58, 12514. doi: 10.1002/anie.201906825 pmid: 31245895
	(g) Chen, X.-L.; Wu, C.-Y.; Yang, D.-S.; Tang, B.-C.; Wang, H.-Y.; Yu, Z.-C.; Li, A.; Wu, Y.-D.; Wu, A.-X. Chin. J. Chem. 2024, 42, 1360. doi: 10.1002/cjoc.v42.12 pmid: 31245895
[8]	(a) Xiao, T.; Li, L.; Zhou, L. J. Org. Chem. 2016, 81, 7908. doi: 10.1021/acs.joc.6b01620
	(b) Lang, S.; Wiles, R. J.; Kelly, C. B.; Molander, G. A. Angew. Chem. Int. Ed. 2017, 56, 15073. doi: 10.1002/anie.v56.47
	(c) Guo, Y.-Q.; Wang, R.; Song, H.; Liu, Y.; Wang, Q. Org. Lett. 2020, 22, 709. doi: 10.1021/acs.orglett.9b04504
	(d) Yue, F.; Liu, J.; Ma, H.; Liu, Y.; Dong, J.; Wang, Q. Org. Lett. 2022, 24, 4019. doi: 10.1021/acs.orglett.2c01448
	(e) Tang, M.; Feng, B.; Bao, Y.; Xu, Z.; Huang, C.; Zheng, H.; Zhu, G.; Wang, Y.; Yuan, Z. Chin. J. Chem. 2024, 42, 2203. doi: 10.1002/cjoc.v42.18
	(f) Chen, M.-X.; Fan, X.-L.; Wang, Z.-Y.; Zhu, Y.-L.; Zhao, X.; Jia, Z.; Hu, X.-H. Org. Chem. Front. 2025, 12, 4476. doi: 10.1039/D5QO00369E
[9]	(a) Gao, X.-T.; Zhang, Z.; Wang, X.; Tian, J.-S.; Xie, S.-L.; Zhou, F.; Zhou, J. Chem. Sci. 2020, 11, 10414. doi: 10.1039/D0SC04091F
	(b) Liu, Y.; Tao, X.; Mao, Y.; Yuan, X.; Qiu, J.; Kong, L.; Ni, S.; Guo, K.; Wang, Y.; Pan, Y. Nat. Commun. 2021, 12, 6745. doi: 10.1038/s41467-021-27060-7
	(c) Zhang, H.; Liang, M.; Zhang, X.; He, M.; Yang, C.; Guo, L.; Xia, W. Org. Chem. Front. 2022, 9, 95. doi: 10.1039/D1QO01460A
[10]	(a) Fuchibe, K.; Hatta, H.; Oh, K.; Oki, R.; Ichikawa, J. Angew. Chem., Int. Ed. 2017, 56, 5890. doi: 10.1002/anie.v56.21
	(b) Liu, Z.; Tu, X.-H.; Guo, L.-T.; Wang, X.-C. Chem. Sci. 2020, 11, 11548. doi: 10.1039/D0SC03883K
[11]	(a) Ichitsuka, T.; Fujita, T.; Ichikawa, J. ACS Catal. 2015, 5, 5947. doi: 10.1021/acscatal.5b01463 pmid: 34162201
	(b) Hayashi, T.; Huang, Y. J. Am. Chem. Soc. 2016, 138, 12340. doi: 10.1021/jacs.6b07844 pmid: 34162201
	(c) Liu, Y.; Zhou, Y.; Zhao, Y.; Qu, J. Org. Lett. 2017, 19, 946. doi: 10.1021/acs.orglett.7b00168 pmid: 34162201
	(d) Dai, W.; Lin, Y.; Wan, Y.; Cao, S. Org. Chem. Front. 2018, 5, 55. doi: 10.1039/C7QO00716G pmid: 34162201
	(e) Wang, M.; Pu, X.; Zhao, Y.; Wang, P.; Li, Z.; Zhu, C.; Shi, Z. J. Am. Chem. Soc. 2018, 140, 9061. doi: 10.1021/jacs.8b04902 pmid: 34162201
	(f) Kojima, R.; Akiyama, S.; Ito, H. Angew. Chem. In. Ed. 2018, 57, 7196. doi: 10.1002/anie.v57.24 pmid: 34162201
	(g) Paioti, P. H. S.; Pozo, J.; Mikus, M. S.; Lee, J.; Koh, M. J.; Romiti, F.; Hoveyda, A. H. J. Am. Chem. Soc. 2019, 141, 19917. doi: 10.1021/jacs.9b11382 pmid: 34162201
	(h) Chen, F.; Xu, X.; He, Y.; Huang, G.; Zhu, S. Angew. Chem., Int. Ed. 2020, 59, 5398. doi: 10.1002/anie.v59.13 pmid: 34162201
	(i) Yao, C.; Wang, S.; Norton, J.; Hammond, M. J. Am. Chem. Soc. 2020, 142, 4793. doi: 10.1021/jacs.9b13757 pmid: 34162201
	(j) Zhu, C.; Liu, Z.-Y.; Tang, L.; Zhang, H.; Zhang, Y.-F.; Walsh, P. J.; Feng, C. Nat. Commun. 2020, 11, 4860. doi: 10.1038/s41467-020-18658-4 pmid: 34162201
	(k) Chen, R.; Sang, Y.; Gao, X.; Zhang, S.; Xue, X.-S.; Zhang, X. Angew. Chem., Int. Ed. 2021, 60, 12386. doi: 10.1002/anie.v60.22 pmid: 34162201
	(l) Pan, Q.; Ping, Y.; Wang, Y.; Guo, Y.; Kong, W. J. Am. Chem. Soc. 2021, 143, 10282. doi: 10.1021/jacs.1c03827 pmid: 34162201
	(m) Yan, X.; Wang, S.; Liu, Z.; Luo, Y.; Wang, P.; Shi, W.; Qi, X.; Huang, Z.; Lei, A. Sci. China Chem. 2022, 65, 762. doi: 10.1007/s11426-021-1210-y pmid: 34162201
	(n) Wang, K.; Chen, J.; Liu, W.; Kong, W. Angew. Chem. Int. Ed. 2022, 61, e202212664. doi: 10.1002/anie.v61.46 pmid: 34162201
	(o) Shinde, P. S.; Shinde, V. S.; Zhu, C.; Rueping, M. ACS Catal. 2025, 15, 17198. doi: 10.1021/acscatal.5c05140 pmid: 34162201
	(p) Li, Z.; Luo, M.; Zeng, X. Org. Biomol. Chem. 2025, 23, 5293. doi: 10.1039/D5OB00547G pmid: 34162201
[12]	(a) Lan, Y.; Yang, F.; Wang, C. ACS Catal. 2018, 8, 9245. doi: 10.1021/acscatal.8b02784
	(b) Lin, Z.; Lan, Y.; Wang, C. ACS Catal. 2019, 9, 775. doi: 10.1021/acscatal.8b04348
	(c) Lin, Z.; Lan, Y.; Wang, C. Org. Lett. 2019, 21, 8316. doi: 10.1021/acs.orglett.9b03102
	(d) Ding, D.; Lan, Y.; Lin, Z.; Wang, C. Org. Lett. 2019, 21, 2723. doi: 10.1021/acs.orglett.9b00692
	(e) Lin, Z.; Lan, Y.; Wang, C. Org. Lett. 2020, 22, 3509. doi: 10.1021/acs.orglett.0c00960
	(f) Jin, Y.; Wu, J.; Lin, Z.; Lan, Y.; Wang, C. Org. Lett. 2020, 22, 5347. doi: 10.1021/acs.orglett.0c01592
	(g) Zhang, C.; Lin, Z.; Zhu, Y.; Wang, C. J. Am. Chem. Soc. 2021, 143, 11602. doi: 10.1021/jacs.1c04531
	(h) Zhang, C.; Wang, L.; Shi, H.; Lin, Z.; Wang, C. Org. Lett. 2022, 24, 3211. doi: 10.1021/acs.orglett.2c00979
	(i) Dong, H.; Lin, Z.; Wang, C. J. Org. Chem. 2022, 87, 892. doi: 10.1021/acs.joc.1c02674
	(j) Yuan, B.; Zhang, C.; Dong, H.; Wang, C. Org. Lett. 2023, 25, 1883. doi: 10.1021/acs.orglett.3c00398
	(k) Dong, H.; Lin, Z.; Wang, C. Adv. Synth. Catal. 2023, 365, 1165. doi: 10.1002/adsc.v365.8
	(l) Shi, H.; Dong, H.; Wang, C. Org. Chem. Front. 2023, 10, 5843. doi: 10.1039/D3QO01331F
[13]	(a) Liang, Z.; Xue, W.; Lin, K.; Gong, H. Org. Lett. 2014, 16, 5620. doi: 10.1021/ol502682q pmid: 25685312
	(b) Liu, J.-H.; Yang, C.-T.; Lu, X.-Y.; Zhang, Z.-Q.; Xu, L.; Cui, M.; Lu, X.; Xiao, B.; Fu, Y.; Liu, L. Chem. Eur. J. 2014, 20, 15334. doi: 10.1002/chem.v20.47 pmid: 25685312
	(c) Molander, G. A.; Traister, K. M.; O’Neill, B. T. J. Org. Chem. 2015, 80, 29071. pmid: 25685312
	(d) Ackerman, L. K. G.; Anka-Lufford, L. L.; Naodovic, M.; Weix, D. J. Chem. Sci. 2015, 6, 1115. doi: 10.1039/C4SC03106G pmid: 25685312
	(e) Wang, J.; Zhao, J.; Gong, H. Chem. Commun. 2017, 53, 10180. doi: 10.1039/C7CC06106D pmid: 25685312
	(f) Komeyama, K.; Ohata, R.; Kiguchi, S.; Osaka, I. Chem. Commun. 2017, 53, 6401. doi: 10.1039/C7CC01932G pmid: 25685312
	(g) Komeyama, K.; Michiyuki, T.; Osaka, I. ACS Catal. 2019, 9, 9285. doi: 10.1021/acscatal.9b03352 pmid: 25685312
	(h) Ibrahim, M. Y. S.; Cumming, G. R.; Vega, R. G.; Garcia-Losada, P.; Frutos, O.; Kappe, C. O.; Cantillo, D. J. Am. Chem. Soc. 2023, 145, 31, 17023. pmid: 25685312
	(i) Wang, R.; Xu, J.; Li, J.-X.; Wu, B.-B.; Jin, R.-X.; Bi, Y.-X.; Wang, X.-S. Chin. Chem. Lett. 2023, 34, 108490. doi: 10.1016/j.cclet.2023.108490 pmid: 25685312
	(j) Li, Z.-H.; Peng, H.; Zhang, P.; Hu, Y.-A.; Pi, C.; Zhu, C.; Xu, H. Org. Chem. Front. 2024, 11, 5010. doi: 10.1039/D4QO01033G pmid: 25685312
[14]	Lin, P. C.; Joshi, C.; McGinnis, T. M.; Mallojjala, S. C.; Sanford, A. B.; Hirschi, J. S.; Jarvo, E. R. ACS Catal. 2023, 13, 4488. doi: 10.1021/acscatal.3c00257

Entry	Ln	Precatalyst	Solvent (V∶V)	Yield^b/%	Entry	Ln	Precatalyst	Solvent (V∶V)	Yield^b/%
1	L1	Ni(dme)Br₂	THF/DMA (4∶1)	38	11	L7	Ni(dme)Br₂	THF/DMA (1∶1)	49
2	L2	Ni(dme)Br₂	THF/DMA (4∶1)	41	12	L7	Ni(dme)Br₂	THF/DMA (1∶4)	69
3	L3	Ni(dme)Br₂	THF/DMA (4∶1)	24	13	L7	NiBr₂	THF/DMA (1∶4)	58
4	L4	Ni(dme)Br₂	THF/DMA (4∶1)	Trace	14	L7	NiCl₂	THF/DMA (1∶4)	52
5	L5	Ni(dme)Br₂	THF/DMA (4∶1)	40	15	L7	Ni(OTf)₂	THF/DMA (1∶4)	24
6	L6	Ni(dme)Br₂	THF/DMA (4∶1)	Trace	16	L7	Ni(acac)₂	THF/DMA (1∶4)	40
7	L7	Ni(dme)Br₂	THF/DMA (4∶1)	58	17^c	L7	Ni(dme)Br₂	THF/DMA (1∶4)	90
8	L7	Ni(dme)Br₂	THF	47	18^c^,^d	L7	Ni(dme)Br₂	THF/DMA (1∶4)	0
9	L7	Ni(dme)Br₂	DMA	34	19^c^,^e	L7	Ni(dme)Br₂	THF/DMA (1∶4)	81
10	L7	Ni(dme)Br₂	MeCN	23

Entry	Ln	Precatalyst	Solvent (V∶V)	Yield^b/%	Entry	Ln	Precatalyst	Solvent (V∶V)	Yield^b/%
1	L1	Ni(dme)Br₂	THF/DMA (4∶1)	38	11	L7	Ni(dme)Br₂	THF/DMA (1∶1)	49
2	L2	Ni(dme)Br₂	THF/DMA (4∶1)	41	12	L7	Ni(dme)Br₂	THF/DMA (1∶4)	69
3	L3	Ni(dme)Br₂	THF/DMA (4∶1)	24	13	L7	NiBr₂	THF/DMA (1∶4)	58
4	L4	Ni(dme)Br₂	THF/DMA (4∶1)	Trace	14	L7	NiCl₂	THF/DMA (1∶4)	52
5	L5	Ni(dme)Br₂	THF/DMA (4∶1)	40	15	L7	Ni(OTf)₂	THF/DMA (1∶4)	24
6	L6	Ni(dme)Br₂	THF/DMA (4∶1)	Trace	16	L7	Ni(acac)₂	THF/DMA (1∶4)	40
7	L7	Ni(dme)Br₂	THF/DMA (4∶1)	58	17^c	L7	Ni(dme)Br₂	THF/DMA (1∶4)	90
8	L7	Ni(dme)Br₂	THF	47	18^c^,^d	L7	Ni(dme)Br₂	THF/DMA (1∶4)	0
9	L7	Ni(dme)Br₂	DMA	34	19^c^,^e	L7	Ni(dme)Br₂	THF/DMA (1∶4)	81
10	L7	Ni(dme)Br₂	MeCN	23

[1]	Lizhuo Wang, Xinyi Liu, Geyang Song, Xiaoli Shi, Dong Xue. Photoexcitation-Enabled C(sp²)—N Coupling of Aryl Halides with Sulfonamides Catalyzed by Earth-Abundant Nickel [J]. Chinese Journal of Organic Chemistry, 2026, 46(7): 2835-2852.
[2]	Dongping Wang, Yuxin Zhang, Shanshan Wei, Fengjiao Wang, Congjun Zhu. Recent Advances in Photoredox Nickel-Catalyzed Deoxygenative Coupling of Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2026, 46(7): 2669-2682.
[3]	Yonglong Zheng, Xinlong Luo, Yumin Xu, Haohua Huo. Metal/Photoredox-Catalyzed C(sp³)—C(sp³) Cross-Electrophile Coupling [J]. Chinese Journal of Organic Chemistry, 2026, 46(7): 2589-2603.
[4]	Xiong She, Hao Cui, Xiao Zhang. Research Progress on Reductive Defluorination of Polytetrafluoroethylene (PTFE) [J]. Chinese Journal of Organic Chemistry, 2026, 46(6): 2241-2248.
[5]	Jingjing Wang, Zihan Yu, Kaihua Yue, Maocong Yi, Andong Zhang, Tonghui Ding, Cuijie Wang, Mingyue Cui, Kechao Liao, Feng Li. Silver-Catalyzed Decarboxylative C—H Alkylation of Cyclic Aldimines with Monoalkyl Oxalates [J]. Chinese Journal of Organic Chemistry, 2026, 46(5): 2096-2103.
[6]	Yunyi Zhang, Hanbing Yan, Xianjin Zhu, Yongjia Shi, Junxin Li, Daoshan Yang, Xufeng Li. Nickel-Catalyzed Reductive Cascade Arylalkylation of Alkenes with Cyclosulfonium Salts [J]. Chinese Journal of Organic Chemistry, 2026, 46(2): 653-663.
[7]	Yuan Liang, Chao Gui, Wenwen Wang, Xueqiang Chu, Hao Xu, Zhiliang Shen. Nickel-Catalyzed Borylation of Aryl Nonaflates for the Efficient Synthesis of Arylboronates via C—O Bond Functionalization [J]. Chinese Journal of Organic Chemistry, 2026, 46(1): 207-214.
[8]	Wen Xu, Meiming Luo, Xiaoming Zeng. Cr-Catalyzed Reductive Cross-Coupling of Trifluoromethyl Alkenes [J]. Chinese Journal of Organic Chemistry, 2025, 45(9): 3401-3411.
[9]	Haichen Ma, Junqian Zhou, Jiali Wang, You Wang, Shaolin Zhu. Recent Advances in Ni-Catalyzed Migratory Cross-Coupling Reactions [J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 1871-1904.
[10]	Shentong Xie, Wenjing Li, Yu Liu, Xi Lu, Renyi Shi. Ni-Catalyzed Reductive Alkylation of Polyfluoroarenes with Alkyl Halides [J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 2121-2127.
[11]	Genwei Gao, Zhen Li, Yan Li, Xi Lu. Recent Progress on the Construction of C(sp²)—C(sp³) Bonds via Photoredox/Nickel Dual Catalysis [J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 1905-1919.
[12]	Fangfang Tan, Mengxin Shi, Wenmin Zhang, Yang Li. Photoinduced Catalysis for Biomass-Related Conversions [J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1523-1547.
[13]	Xiaonan Mu, Minhui Guan, Yulong Niu, Hao Chen, Chuanying Li, Lei Wang. Synthesis of Difluorocyclopropanes via a Photoinduced [1＋2] Cycloaddition of Diazo Esters with gem-Difluoroalkenes [J]. Chinese Journal of Organic Chemistry, 2025, 45(1): 256-266.
[14]	Chao Sun, Quan Zhou, Chuanying Li, Lei Wang. Syntheses and Structural Characterizations of Benzoxazolyl N-Heterocyclic Carbene-Palladium Complexes and Their Applications [J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1957-1966.
[15]	Yunxin Xing, Denghong Yan, Shun Wen, Jie Bu, Kun Shen. Nickel-Catalyzed Reductive anti-Arylative Cyclization of 1,6-Enynes with Aryl Halides [J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1938-1948.

镍催化三氟甲基取代烯烃与烷基甲磺酸酯的烯丙位脱氟交叉亲电偶联