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Synthesis
DOI: 10.1055/a-2457-0319
DOI: 10.1055/a-2457-0319
paper
Dual Catalysis
Synergistic Pd/Cu-Catalyzed Asymmetric Csp3–Csp3 Coupling of 1,3-Dienes with 2-Acylimidazoles
We gratefully acknowledge the National Key Research and Development Program of China (2022YFA1503700), the National Natural Science Foundation of China (22071118, 22271162, and 22188101), the Natural Science Foundation of Tianjin Municipality (21JCZDJC00350), and the Haihe Laboratory of Sustainable Chemical Transformations and Frontiers Science Center for New Organic Matter, Nankai University for financial support.
Abstract
The catalytic asymmetric coupling of 1,3-dienes with carbon nucleophiles is an important process for forming Csp3–Csp3 bonds. Here, we describe a synergistic Pd/Cu-catalyzed coupling of 1,3-dienes with 2-acylimidazoles. This reaction produces 2-acylimidazole derivatives that have α,β-adjacent stereocenters in moderate yields with good to excellent stereoselectivity.
Key words
synergistic catalysis - palladium - copper - Csp3–Csp3 coupling - 2-acylimidazoles - 1,3-dienesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2457-0319.
- Supporting Information
- CIF File
Publication History
Received: 20 September 2024
Accepted after revision: 29 October 2024
Accepted Manuscript online:
29 October 2024
Article published online:
03 December 2024
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References
- 1 Adamson NJ, Malcolmson SJ. ACS Catal. 2020; 10: 1060
- 2 Cheng L, Li M.-M, Xiao L.-J, Xie J.-H, Zhou Q.-L. J. Am. Chem. Soc. 2018; 140: 11627
- 3 Adamson NJ, Wilbur KC. E, Malcolmson SJ. J. Am. Chem. Soc. 2018; 140: 2761
- 4 Shao W, Besnard C, Guénée L, Mazet C. J. Am. Chem. Soc. 2020; 142: 16486
- 5 Wang H, Zhang Q, Zi W. Acc. Chem. Res. 2024; 57: 468
- 6 Zhang Q, Yu H, Shen L, Tang T, Dong D, Chai W, Zi W. J. Am. Chem. Soc. 2019; 141: 14554
- 7 Wang H, Zhang R, Zhang Q, Zi W. J. Am. Chem. Soc. 2021; 143: 10948
- 8 Zhang Q, Zhu M, Zi W. Chem 2022; 8: 2784
- 9 Han J, Liu R, Lin Z, Zi W. Angew. Chem. Int. Ed. 2023; 62: e202215714
- 10 Lauberteaux J, Pichon D, Baslé O, Mauduit M, de Figueiredo RM, Campagne J.-M. ChemCatChem 2019; 11: 5705
- 11 Xiong P, Hemming M, Ivlev SI, Meggers E. J. Am. Chem. Soc. 2022; 144: 6964
- 12 Simpson A, Lam H. Org. Lett. 2013; 15: 2586
- 13 Hou X, Ma H, Zhang Z, Xie L, Qin Z, Fu B. Chem. Commun. 2016; 52: 1470
- 14 Xu G, Liang H, Fang J. Chem. Asian J. 2016; 11: 3355
- 15 Huo H, Wang C, Harms K, Meggers E. J. Am. Chem. Soc. 2015; 137: 9551
- 16 Tan Y, Yuan W, Gong L, Meggers E. Angew. Chem. Int. Ed. 2015; 54: 13045
- 17 Wu F, Li Z, Fu C, Wang G, Zheng C, Wu X. Org. Lett. 2023; 25: 5448
- 18 Lu R, Zhang Q, Guo C. Nat. Commun. 2023; 14: 8118
- 19 Wei L, Chang X, Wang C.-J. Acc. Chem. Res. 2020; 53: 1084
- 20 Wu Y, Huo X, Zhang W. Chem. Eur. J. 2020; 26: 4895
- 21 Wei L, Wang C.-J. Chem Catal. 2023; 3: 100455
- 22 Wei L, Fu C, Wang Z.-F, Tao H.-Y, Wang C.-J. ACS Catal. 2024; 14: 3812
- 23 Huo X, He R, Fu J, Zhang J, Yang G, Zhang W. J. Am. Chem. Soc. 2017; 139: 9819
- 24 Wei L, Xu S.-M, Zhu T, Che C, Wang C.-J. Angew. Chem. Int. Ed. 2017; 56: 12312
- 25 Zhu M, Zhang Q, Zi W. Angew. Chem. Int. Ed. 2021; 60: 6545
- 26 Yang S.-Q, Wang Y.-F, Zhao W.-C, Lin G.-Q, He Z.-T. J. Am. Chem. Soc. 2021; 143: 7285
- 27 Yu H, Zhang Q, Zi W. Angew. Chem. Int. Ed. 2022; 61: e202208411
- 28 Chai W, Guo B, Zhang Q, Zi W. Chem Catal. 2022; 2: 1428
- 29 Chang X, Ran J.-D, Liu X.-T, Wang C.-J. Org. Lett. 2022; 24: 2573
- 30 Wang H, Zhang R, Zi W. Angew. Chem. Int. Ed. 2024; 63: e202402843
- 31 Li P, Zheng E, Li G, Luo Y, Huo X, Ma S, Zhang W. Science 2024; 385: 972
- 32 Zhu W, Han C, Yang G, Huo X, Zhang W. J. Am. Chem. Soc. 2024; 146: 26121
- 33 Li P, Liu Z, Huo X, Zhang W. Angew. Chem. Int. Ed. 2024; 63: e202407498
- 34 Zhang J, Luo Y, Zheng E, Huo X, Ma S, Zhang W. J. Am. Chem. Soc. 2024; 146: 9241
- 35 Zhang Q, Dong D, Zi W. J. Am. Chem. Soc. 2020; 142: 15860
- 36 Sun S, Zhang Q, Zi W. ACS Catal. 2023; 13: 12952
- 37 Huo X, Li G, Wang X, Zhang W. Angew. Chem. Int. Ed. 2022; 61: e202210086
- 38 CCDC 2356293 [(2S,3R)-3af] contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures