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DOI: 10.1055/a-2204-8921
Phosphine Ligand Effects in Nickel-Catalyzed Alkene Migratory Hydroalkylation
Financial support was received from the National Science Foundation of Anhui Province (2208085J26 and 2208085QB36) and the China Postdoctoral Science Foundation (2023TQ0343)
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Abstract
Catalytic alkene hydroalkylation has provided to be an efficient method for synthesizing C(sp3) centers, from readily available and inexpensive alkene starting materials through alkene hydrometallation followed by cross-coupling. One of the major tasks in this field is to develop diverse ligands to achieve regioselective control. Herein, we report the investigation of nickel–triphenylphosphine-catalyzed remote hydroalkylation of alkenyl amides to access α-branched amines. Various alkenes and alkyl iodides are suitable substrates to deliver the desired products with excellent regioselectivities (>20:1 regioisomeric ratio). Density functional theory calculations reveal the reaction mechanism.
Key words
alkene hydroalkylation - nickel catalysis - phosphine ligand effects - migratory hydroalkylation - alkenyl amides - α-branched aminesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2204-8921.
- Supporting Information
Publication History
Received: 12 October 2023
Accepted after revision: 06 November 2023
Accepted Manuscript online:
06 November 2023
Article published online:
04 December 2023
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References
- 1a Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011; 111: 1417
- 1b Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299
- 1c Cherney AH, Kadunce NT, Reisman SE. Chem. Rev. 2015; 115: 9587
- 1d Lu X, Xiao B, Shang R, Liu L. Chin. Chem. Lett. 2016; 27: 305
- 1e Juliá-Hernández F, Moragas T, Cornella J, Martin R. Nature 2017; 545: 84
- 1f Choi J, Fu GC. Science 2017; 356: eaaf7230
- 1g Lu X, He S.-J, Cheng W.-M, Shi J. Chin. Chem. Lett. 2018; 29: 1001
- 1h Lv X.-Y, Fan C, Xiao L.-J, Xie J.-H, Zhou Q.-L. CCS Chem. 2019; 1: 328
- 1i Zhang G, Liu Y, Zhao J, Li Y, Zhang Q. Sci. China: Chem. 2019; 62: 1476
- 1j Liu RY, Buchwald SL. Acc. Chem. Res. 2020; 53: 1229
- 1k Wu X, Ren J, Shao Z, Yang X, Qian D. ACS Catal. 2021; 11: 6560
- 1l Wang B, Zhang T, Xiao L.-J, Zhou Q.-L. ACS Catal. 2023; 13: 8692
- 2a Li W, Boon JK, Zhao Y. Chem. Sci. 2018; 9: 600
- 2b Belal M, Li Z, Lu X, Yin G. Sci. China: Chem. 2021; 64: 513
- 2c Wickham LM, Giri R. Acc. Chem. Res. 2021; 54: 3415
- 3a Maksymowicz RM, Roth PM. C, Fletcher SP. Nat. Chem. 2012; 4: 649
- 3b Wang X.-X, Lu X, Li Y, Wang J.-W, Fu Y. Sci. China: Chem. 2020; 63: 1586
- 3c Sun X.-Y, Yao B.-Y, Xuan B, Xiao L.-J, Zhou Q.-L. Chem Catal. 2022; 2: 3140
- 3d He Y, Chen J, Jiang X, Zhu S. Chin. J. Chem. 2022; 40: 651
- 3e Zhang Z, Bera S, Fan C, Hu X. J. Am. Chem. Soc. 2022; 144: 7015
- 3f Yang P.-F, Shu W. Chem Catal. 2023; 3: 100508
- 4a Vasseur A, Bruffaerts J, Marek I. Nat. Chem. 2016; 8: 209
- 4b Sommer H, Juliá-Hernández F, Martin R, Marek I. ACS Cent. Sci. 2018; 4: 153
- 4c Qian D, Hu X. Angew. Chem. Int. Ed. 2019; 58: 18519
- 4d Janssen-Müller D, Sahoo B, Sun S.-Z, Martin R. Isr. J. Chem. 2020; 60: 195
- 4e Yu R, Rajasekar S, Fang X. Angew. Chem. Int. Ed. 2020; 59: 21436
- 4f Chen J, Zhu S. J. Am. Chem. Soc. 2021; 143: 14089
- 4g Ding C, Ren Y, Sun C, Long J, Yin G. J. Am. Chem. Soc. 2021; 143: 20027
- 4h Wang Y, He Y, Zhu S. Acc. Chem. Res. 2022; 55: 3519
- 4i Zhao L, Zhu Y, Liu M, Xie L, Liang J, Shi H, Meng X, Chen Z, Han J, Wang C. Angew. Chem. Int. Ed. 2022; 61: e202204716
- 4j Cui K, Li Y.-L, Li G, Xia J.-B. J. Am. Chem. Soc. 2022; 144: 23001
- 4k Wang X, Xue J, Rong Z.-Q. J. Am. Chem. Soc. 2023; 145: 15456
- 5a Chen J, Guo J, Lu Z. Chin. J. Chem. 2018; 36: 1075
- 5b Sun S.-Z, Börjesson M, Martin-Montero R, Martin R. J. Am. Chem. Soc. 2018; 140: 12765
- 5c Diccianni JB, Diao T. Trends Chem. 2019; 1: 830
- 5d Sun S.-Z, Romano C, Martin R. J. Am. Chem. Soc. 2019; 141: 16197
- 5e Yang Z.-P, Fu GC. J. Am. Chem. Soc. 2020; 142: 5870
- 5f Cuesta-Galisteo S, Schörgenhumer J, Wei X, Merino E, Nevado C. Angew. Chem. Int. Ed. 2021; 60: 1605
- 5g Gao J, Jiao M, Ni J, Yu R, Cheng G.-J, Fang X. Angew. Chem. Int. Ed. 2021; 60: 1883
- 5h Qian D, Bera S, Hu X. J. Am. Chem. Soc. 2021; 143: 1959
- 5i Wang S, Zhang J.-X, Zhang T.-Y, Meng H, Chen B.-H, Shu W. Nat. Commun. 2021; 12: 2771
- 5j Bera S, Fan C, Hu X. Nat. Catal. 2022; 5: 1180
- 5k Chen J, Ying J, Lu Z. Nat. Commun. 2022; 13: 4518
- 5l Huang Q, Chen Y, Zhou X, Dai L, Lu Y. Angew. Chem. Int. Ed. 2022; 61: e202210560
- 5m Zeng M, Yu C, Wang Y, Wang J, Wang J, Liu H. Angew. Chem. Int. Ed. 2023; 62: e202300424
- 5n Ke Y, Li W, Liu W, Kong W. Sci. China: Chem. 2023; 66: 2951
- 5o Rodrigalvarez J, Wang H, Martin R. J. Am. Chem. Soc. 2023; 145: 3869
- 6 Lu X, Xiao B, Zhang Z, Gong T, Su W, Yi J, Fu Y, Liu L. Nat. Commun. 2016; 7: 11129
- 7 He Y, Cai Y, Zhu S. J. Am. Chem. Soc. 2017; 139: 1061
- 8 Wang Z, Yin H, Fu GC. Nature 2018; 563: 379
- 9 Bera S, Mao R, Hu X. Nat. Chem. 2021; 13: 270
- 10 Li Y, Nie W, Chang Z, Wang J.-W, Lu X, Fu Y. Nat. Catal. 2021; 4: 901
- 11a Lee C, Seo H, Jeon J, Hong S. Nat. Commun. 2021; 12: 5657
- 11b Zhang Y, He J, Song P, Wang Y, Zhu S. CCS Chem. 2020; 2: 2259
- 12 Chen X, Rao W, Yang T, Koh MJ. Nat. Commun. 2020; 11: 5857
- 13a Lu X, Zhang Z.-Q, Yu L, Zhang B, Wang B, Gong T.-J, Tian C.-L, Xiao B, Fu Y. Chin. J. Chem. 2019; 37: 11
- 13b He S.-J, Wang J.-W, Li Y, Xu Z.-Y, Wang X.-X, Lu X, Fu Y. J. Am. Chem. Soc. 2020; 142: 214
- 13c Wang J.-W, Li Y, Nie W, Chang Z, Yu Z.-A, Zhao Y.-F, Lu X, Fu Y. Nat. Commun. 2021; 12: 1313
- 13d Li Z, Wang J, Lu X, Fu Y. JUSTC 2022; 52: 1
- 13e Wang X.-X, Yu L, Lu X, Zhang Z.-L, Liu D.-G, Tian C, Fu Y. CCS Chem. 2022; 4: 605
- 13f Wang X.-X, Xu Y.-T, Zhang Z.-L, Lu X, Fu Y. Nat. Commun. 2022; 13: 1890
- 13g Li Y, Liu D, Wan L, Zhang J.-Y, Lu X, Fu Y. J. Am. Chem. Soc. 2022; 144: 13961
- 13h Wang J.-W, Liu D.-G, Chang Z, Li Z, Fu Y, Lu X. Angew. Chem. Int. Ed. 2022; 61: e202205537
- 13i Wang J.-W, Li Z, Liu D, Zhang J.-Y, Lu X, Fu Y. J. Am. Chem. Soc. 2023; 145: 10411
- 13j Liu B, Liu D, Rong X, Lu X, Fu Y, Liu Q. Angew. Chem. Int. Ed. 2023; 62: e202218544
- 13k Zhang Z.-L, Li Z, Xu Y.-T, Yu L, Kuang J, Li Y, Wang J.-W, Tian C, Lu X, Fu Y. Angew. Chem. Int. Ed. 2023; 62: e202306381
- 14 Li Y, Luo Y, Peng L, Li Y, Zhao B, Wang W, Pang H, Deng Y, Bai R, Lan Y, Yin G. Nat. Commun. 2020; 11: 417