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Synlett
DOI: 10.1055/a-2579-3319
DOI: 10.1055/a-2579-3319
letter
Nickel-Catalyzed Nucleophilic Substitution of Cyclopropenes by Secondary Phosphines
We thank the National Natural Science Foundation of China (NSFC; grant numbers 22071224 and 22471251), and the Chinese Academy of Sciences (CAS) Project for Young Scientists in Basic Research (YSBR-098) for financial support.

Abstract
Research on the efficient synthesis of allylphosphine compounds is of crucial significance. Herein, a nickel-catalyzed ring-opening of cyclopropenes is described to synthesize allylphosphine compounds. This transformation enables a mild and efficient preparation of allylphosphine compounds in good yields, with 100% atom efficiency.
Key words
nickel catalysis - hydrophosphination - secondary phosphines - allylphosphine - C–P constructionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2579-3319.
- Supporting Information
Publication History
Received: 26 February 2025
Accepted after revision: 09 April 2025
Accepted Manuscript online:
09 April 2025
Article published online:
03 June 2025
© 2025. Thieme. All rights reserved
Georg Thieme Verlag KG
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References
- 1a Quin LD. A Guide to Organophosphorus Chemistry . Wiley-VCH; New York: 2000
- 1b Organophosphorus Reagents . Murphy PJ. Oxford University Press; Oxford: 2004
- 1c Zhou QL. In Privileged Chiral Ligands and Catalysts . Wiley-VCH; Weinheim: 2011
- 2a Dutartre M, Bayardon J, Juge S. Chem. Soc. Rev. 2016; 45: 5771
- 2b Horsman GP, Zechel DL. Chem. Rev. 2017; 117: 5704
- 2c Zhang Y, Han DR, Ye D, Lu H, Wei H. Chin. Chem. Lett. 2024; 35: 108529
- 2d Li YB, Li Y, Yin L. Chin. Chem. Lett. 2024; 35: 109294
- 2e Zhu S, Chen MJ, Shen HC, Ding HM, Li WB, Zhang JL. Chin. Chem. Lett. 2024; 35: 109879
- 3a Ni HZ, Chan WL, Lu YX. Chem. Rev. 2018; 118: 9344
- 3b Iaroshenko V. In Organophosphorus Chemistry: From Molecules to Applications. Wiley-VCH; Weinheim: 2019
- 3c Wang BW, Sun LW, Cao QQ, Li XZ, Chen JN, Wang SZ, Ke ML, Chen FE. Chin. Chem. Lett. 2024; 35: 109617
- 4a Binger P, Buch HM. Top. Curr. Chem. 1987; 135: 77
- 4b Fox JM, Yan N. Curr. Org. Chem. 2005; 9: 719
- 4c Rubin M, Rubina M, Gevorgyan V. Synthesis 2006; 1221
- 4d Rubin M, Rubina M, Gevorgyan V. Chem. Rev. 2007; 107: 3117
- 4e Marek I, Simaan S, Masarwa A. Angew. Chem. Int. Ed. 2007; 46: 7364
- 4f Zhu ZB, Wei Y, Shi M. Chem. Soc. Rev. 2011; 40: 5534
- 4g Archambeau A, Miege F, Meyer C, Cossy J. Acc. Chem. Res. 2015; 48: 1021
- 4h Dian LY, Marek I. Chem. Rev. 2018; 118: 8415
- 4i Li PH, Zhang XY, Shi M. Chem. Commun. 2020; 56: 5457
- 5a Hong L, Sun WS, Liu CX, Zhao DP, Wang R. Chem. Commun. 2010; 46: 2856
- 5b Sun WS, Hong L, Liu CX, Wang R. Org. Lett. 2010; 12: 3914
- 5c Dai Q, Li WB, Li ZM, Zhang JL. J. Am. Chem. Soc. 2019; 141: 20556
- 5d Liu XT, Zhang YQ, Han XY. Sun Y. P, Zhang QW. J. Am. Chem. Soc. 2019; 141: 16584
- 5e Wang CY, Yue CD, Yuan J, Zheng JL, Zhang Y, Yu H, Chen J, Meng SX, Yu Y, Yu GA, Che CM. Chem. Commun. 2020; 56: 11775
- 5f Wu ZH, Cheng AQ, Yuan M, Zhao Y.-X, Yang HL, Wei LH, Wang HY, Wang T, Zhang ZT, Duan WL. Angew. Chem. Int. Ed. 2021; 60: 27241
- 5g Zhang S, Xiao JZ, Li YB, Shi CY, Yin L. J. Am. Chem. Soc. 2021; 143: 9912
- 5h Zhang X, Wang J, Yang SD. ACS Catal. 2021; 11: 14008
- 5i Liu SY, Tanabe Y, Kuriyama S, Sakata K, Nishibayashi Y. Angew. Chem. Int. Ed. 2021; 60: 11231
- 5j Zhang Q, Liu XT, Wu Y, Zhang QW. Org. Lett. 2021; 23: 8683
- 6 Alnasleh BK, Sherrill WM, Rubin M. Org. Lett. 2008; 10: 3231
- 7a Li SF, Lu ZW, Meng L, Wang J. Org. Lett. 2016; 18: 5276
- 7b Lu ZW, Zhang HY, Yang ZP, Ding N, Meng L, Wang J. ACS Catal. 2019; 9: 1457
- 7c Li SF, Yang Q, Bian ZX, Wang J. Org. Lett. 2020; 22: 2781
- 7d Yang ZP, Wang J. Angew. Chem. Int. Ed. 2021; 60: 27288
- 8 Zhang YL, Jiang YX, Li ML, Huang ZX, Wang J. Chem Catal. 2022; 2: 3163
- 9a Zhang S, Jiang N, Xiao JZ, Lin GQ, Yin L. Angew. Chem. Int. Ed. 2023; 62: e202218798
- 9b Daniels BS, Hou XT, Corio SA, Weissman LM, Dong VM, Hirschi JS, Nie SZ. Angew. Chem. Int. Ed. 2023; 62: e202306511
- 10 Lin XB, An K, Zhuo QD, Nishiura M, Cong XF, Hou ZM. Angew. Chem. Int. Ed. 2023; 62: e202308488
- 11a Iffland L, Petuker A, Gastel MV, Apfel UP. Inorganics 2017; 5: 78
- 11b Gisbertz S, Reischauer S, Pieber B. Nat. Catal. 2020; 3: 611
- 11c Xue WC, Jia X, Wang X, Tao XH, Yin ZG, Gong HG. Chem. Soc. Rev. 2021; 50: 4162
- 11d Pang XB, Su PF, Shu XZ. Acc. Chem. Res. 2022; 55: 2491
- 12a Liu XT, Han XY, Wu Y, Sun YY, Gao L, Huang Z, Zhang QW. J. Am. Chem. Soc. 2021; 143: 11309
- 12b Wang WH, Wu Y, Wang HT, Qi PJ, Lan WN, Zhang QW. Nat. Synth. 2022; 1: 738
- 12c Zhang YQ, Han XY, Wu Y, Qi PJ, Zhang Q, Zhang QW. Chem. Sci. 2022; 13: 4095
- 12d Cai WQ, Wei Q, Zhang QW. Org. Lett. 2022; 24: 1258
- 12e Zhang Q, Cui RR, Zhang QW. Synlett 2023; 34: 1819
- 12f Wang WH, Wu Y, Qi PJ, Zhang QW. ACS Catal. 2023; 13: 6994
- 12g Huang Z, Liu XT, Cui RR, Zhang QW. Org. Biomol. Chem. 2023; 21: 3096
- 12h Cui RR, Wang YQ, Yuwen LY, Huang Z, Wang WH, Zhang QW. Org. Lett. 2023; 25: 6139
- 12i Li ZY, Peng GC, Zhao JB, Zhang Q. Org. Lett. 2016; 18: 4840
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