Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (5): 431-434.DOI: 10.6023/A23030103 Previous Articles Next Articles
Special Issue: 庆祝《化学学报》创刊90周年合辑
Communication
王瑞祥a, 赵庆如b, 顾庆b,*(), 游书力a,b,*()
投稿日期:
2023-03-30
发布日期:
2023-05-08
作者简介:
基金资助:
Wang Rui-Xianga, Zhao Qing-Rub, Gu Qingb(), You Shu-Lia,b()
Received:
2023-03-30
Published:
2023-05-08
Contact:
*E-mail: qinggu@sioc.ac.cn; slyou@sioc.ac.cn
About author:
Supported by:
Share
Wang Rui-Xiang, Zhao Qing-Ru, Gu Qing, You Shu-Li. Gold/Iridium Catalyzed Alkynylamide Cyclization/Asymmetric Allylic Benzylation Cascade Reaction★[J]. Acta Chimica Sinica, 2023, 81(5): 431-434.
Entry | [Au] (x mol%) | L | Solvent | Yield of 3ab | ee of 3ac |
---|---|---|---|---|---|
1e | Au1 | (Sa)-L1 | DCE | 60% | >99% |
2 | Au1 | (Sa)-L1 | DCE | 95% (87%d) | >99% |
3f | Au1 | (Sa)-L1 | DCE | 94% | >99% |
4 | AuCl3 | (Sa)-L1 | DCE | 68% | >99% |
5 | Ph3PAuCl | (Sa)-L1 | DCE | 50% | >99% |
6 | Me2SAuCl | (Sa)-L1 | DCE | 75% | 49% |
7g | Ph3PAuMe | (Sa)-L1 | DCE | trace | N.D. h |
8 | Au1 | (Sa)-L2 | DCE | 36% | 52% |
9 | Au1 | (Sa)-L3 | DCE | 66% | 96% |
10 | Au1 | (Sa)-L1 | dioxane | 54% | >99% |
11 | Au1 | (Sa)-L1 | THF | 20% | N.D. h |
12 | Au1 | (Sa)-L1 | toluene | 52% | >99% |
13 | Au1 | (Sa)-L1 | MeCN | trace | N.D. h |
14 | Au1 | (Sa)-L1 | CHCl3 | 70% | >99% |
Entry | [Au] (x mol%) | L | Solvent | Yield of 3ab | ee of 3ac |
---|---|---|---|---|---|
1e | Au1 | (Sa)-L1 | DCE | 60% | >99% |
2 | Au1 | (Sa)-L1 | DCE | 95% (87%d) | >99% |
3f | Au1 | (Sa)-L1 | DCE | 94% | >99% |
4 | AuCl3 | (Sa)-L1 | DCE | 68% | >99% |
5 | Ph3PAuCl | (Sa)-L1 | DCE | 50% | >99% |
6 | Me2SAuCl | (Sa)-L1 | DCE | 75% | 49% |
7g | Ph3PAuMe | (Sa)-L1 | DCE | trace | N.D. h |
8 | Au1 | (Sa)-L2 | DCE | 36% | 52% |
9 | Au1 | (Sa)-L3 | DCE | 66% | 96% |
10 | Au1 | (Sa)-L1 | dioxane | 54% | >99% |
11 | Au1 | (Sa)-L1 | THF | 20% | N.D. h |
12 | Au1 | (Sa)-L1 | toluene | 52% | >99% |
13 | Au1 | (Sa)-L1 | MeCN | trace | N.D. h |
14 | Au1 | (Sa)-L1 | CHCl3 | 70% | >99% |
[1] |
(a) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921.
doi: 10.1021/cr020027w |
(b) Lu, Z.; Ma, S. Angew. Chem. Int. Ed. 2008, 47, 258.
|
|
(c) Weaver, J. D.; Recio, A., III; Grenning, A. J.; Tunge, J. A. Chem. Rev. 2011, 111, 1846.
doi: 10.1021/cr1002744 |
|
For a book, see:
|
|
(d) Transition Metal Catalyzed Enantioselective Allylic Substitution: Organic Synthesis, Ed.: Kazmaier, U., Springer,eidelberg, 2012.
|
|
[2] |
(a) Heterocycles in Natural Product Synthesis, Eds.: Majumdar, K. C.; Chattopadhyay, S. K., Wiley-VCH,Weinheim, 2011.
pmid: 25255204 |
(b) Metalation of Azoles and Related Five-Membered Ring Heterocycles: Topics in Heterocyclic Chemistry, Vol. 29, Ed.: Gribble, G. W., Springer, Heidelberg, 2012.
pmid: 25255204 |
|
(c) Heteroocyclic Chemistry in Drug Discovery, Ed.: Li, J.-J., Wiley, Hoboken, 2013.
pmid: 25255204 |
|
(d) Roughley, S. D.; Jordan, A. M. J. Med. Chem. 2011, 54, 3451.
doi: 10.1021/jm200187y pmid: 25255204 |
|
(e) Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257.
doi: 10.1021/jm501100b pmid: 25255204 |
|
[3] |
(a) Trost, B. M.; Thaisrivongs, D. A. J. Am. Chem. Soc. 2008, 130, 14092.
doi: 10.1021/ja806781u |
(b) Trost, B. M.; Thaisrivongs, D. A. J. Am. Chem. Soc. 2009, 131, 12056.
doi: 10.1021/ja904441a |
|
(c) Trost, B. M.; Thaisrivongs, D. A.; Hartwig, J. J. Am. Chem. Soc. 2011, 133, 12439.
doi: 10.1021/ja205523e |
|
[4] |
(a) Sha, S.-C.; Jiang, H.; Mao, J.; Bellomo, A.; Jeong, S. A.; Walsh, P. J. Angew. Chem. Int. Ed. 2016, 55, 1070.
doi: 10.1002/anie.v55.3 |
(b) Mao, J.; Zhang, J.; Jiang, H.; Bellomo, A.; Zhang, M.; Gao, Z.; Dreher, S. D.; Walsh, P. J. Angew. Chem. Int. Ed. 2016, 55, 2526.
doi: 10.1002/anie.v55.7 |
|
[5] |
(a) Mosrin, M.; Knochel, P. Org. Lett. 2009, 11, 1837.
doi: 10.1021/ol900342a pmid: 19317432 |
(b) Duez, S.; Steib, A. K.; Manolikakes, S. M.; Knochel, P. Angew. Chem. Int. Ed. 2011, 50, 7686.
doi: 10.1002/anie.201103074 pmid: 19317432 |
|
(c) Haas, D.; Hammann, J. M.; Greiner, R.; Knochel, P. ACS Catal. 2016, 6, 1540.
doi: 10.1021/acscatal.5b02718 pmid: 19317432 |
|
[6] |
(a) Liu, X.-J.; You, S.-L. Angew. Chem. Int. Ed. 2017, 56, 4002.
doi: 10.1002/anie.201700433 |
(b) Liu, X.-J.; Zhang, W.-Y.; Zheng, C.; You, S.-L. Angew. Chem. Int. Ed. 2022, e202200164.
|
|
[7] |
For selected reviews on Ir-catalyzed asymmetric allylic substitution reactions, see: a Hartwig, J. F.; Stanley, L. M. Acc. Chem. Res. 2010, 43, 1461.
pmid: 28649462 |
(b) Liu, W.-B.; Xia, J.-B.; You, S.-L. Top. Organomet. Chem. 2012, 38, 155.
pmid: 28649462 |
|
(c) Zhuo, C.-X.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2014, 47, 2558.
doi: 10.1021/ar500167f pmid: 28649462 |
|
(d) Hethcox, J. C.; Shockley, S. E.; Stoltz, B. M. ACS Catal. 2016, 6, 6207.
doi: 10.1021/acscatal.6b01886 pmid: 28649462 |
|
(e) Qu, J.; Helmchen, G. Acc. Chem. Res. 2017, 50, 2539.
doi: 10.1021/acs.accounts.7b00300 pmid: 28649462 |
|
(f) Rössler, S. L.; Petrone, D. A.; Carreira, E. M. Acc. Chem. Res. 2019, 52, 2657.
doi: 10.1021/acs.accounts.9b00209 pmid: 28649462 |
|
(g) Cheng, Q.; Tu, H.-F.; Zheng, C.; Qu, J.-P.; Helmchen, G.; You, S.-L. Chem. Rev. 2019, 119, 1855.
doi: 10.1021/acs.chemrev.8b00506 pmid: 28649462 |
|
[8] |
(a) Singha, S.; Serrano, E.; Mondal, S.; Daniliuc, C. G.; Glorius, F. Nat. Catal. 2020, 3, 48.
doi: 10.1038/s41929-019-0387-3 pmid: 35476460 |
(b) Butcher, T. W.; Yang, J. L.; Amberg, W. M.; Watkins, N. B.; Wilkinson, N. D.; Hartwig, J. F. Nature 2020, 583, 548.
doi: 10.1038/s41586-020-2399-1 pmid: 35476460 |
|
(c) Chen, P.; Li, Y.; Chen, Z.-C.; Du, W.; Chen, Y.-C. Angew. Chem. Int. Ed. 2020, 59, 7083.
doi: 10.1002/anie.v59.18 pmid: 35476460 |
|
(d) Han, M.; Yang, M.; Wu, R.; Li, Y.; Jia, T.; Gao, Y.; Ni, H.-L.; Hu, P.; Wang, B.-Q.; Cao, P. J. Am. Chem. Soc. 2020, 142, 13398.
doi: 10.1021/jacs.0c01766 pmid: 35476460 |
|
(e) Tu, H.-F.; Yang, P.; Lin, Z.; Zheng, C.; You, S.-L. Nat. Chem. 2020, 12, 838.
doi: 10.1038/s41557-020-0489-1 pmid: 35476460 |
|
(f) Rossi-Ashton, J. A.; Clarke, A. K.; Donald, J. R.; Zheng, C.; Taylor, R. J. K.; Unsworth, W. P.; You, S.-L. Angew. Chem. Int. Ed. 2020, 59, 7598.
doi: 10.1002/anie.202001956 pmid: 35476460 |
|
(g) Wang, J.; Qi, X.; Min, X.-L.; Yi, W.; Liu, P.; He, Y. J. Am. Chem. Soc. 2021, 143, 10686.
doi: 10.1021/jacs.1c04400 pmid: 35476460 |
|
(h) Davis, C. R.; Luvaga, I. K.; Ready, J. M.; J. Am. Chem. Soc. 2021, 143, 4921.
doi: 10.1021/jacs.1c01242 pmid: 35476460 |
|
(i) Jiang, R.; Ding, L.; Zheng, C.; You, S.-L. Science 2021, 371, 380.
doi: 10.1126/science.abd6095 pmid: 35476460 |
|
(j) Crisenza, G. E. M.; Faraone, A.; Gandolfo, E.; Mazzarella, D.; Melchiorre, P. Nat. Chem. 2021, 13, 575.
doi: 10.1038/s41557-021-00683-5 pmid: 35476460 |
|
(k) Xiao, L.; Wei, L.; Wang, C.-J. Angew. Chem. Int. Ed. 2021, 60, 24930.
doi: 10.1002/anie.v60.47 pmid: 35476460 |
|
(l) Peng, Y.; Huo, X.; Luo, Y.; Wu, L.; Zhang, W. Angew. Chem. Int. Ed. 2021, 60, 24941.
doi: 10.1002/anie.v60.47 pmid: 35476460 |
|
(m) Zhang, M.-M.; Chen, P.; Xiong, W.; Hui, X.-S.; Lu, L.-Q.; Xiao, W.-J. CCS Chem. 2021, 3, 3383.
pmid: 35476460 |
|
(n) Deng, Y.; Liang, X.; Wei, K.; Yang, Y.-R. J. Am. Chem. Soc. 2021, 143, 20622.
doi: 10.1021/jacs.1c11265 pmid: 35476460 |
|
(o) Zhao, Q.-R.; Jiang, R.; You, S.-L. Acta Chim. Sinica 2021, 79, 1107. (in Chinese)
doi: 10.6023/A21070320 pmid: 35476460 |
|
(赵庆如, 蒋茹, 游书力, 化学学报, 2021, 79, 1107.)
doi: 10.6023/A21070320 pmid: 35476460 |
|
(p) Yang, P.-S.; Liu, C.-X.; Zhang, W.-W.; You, S.-L. Acta Chim. Sinica 2021, 79, 742. (in Chinese)
doi: 10.6023/A21050198 pmid: 35476460 |
|
(杨普苏, 刘晨旭, 张文文, 游书力, 化学学报, 2021, 79, 742.)
doi: 10.6023/A21050198 pmid: 35476460 |
|
(q) Ding, L.; Song, H.; Zheng, C.; You, S.-L. J. Am. Chem. Soc. 2022, 144, 4770.
doi: 10.1021/jacs.2c01103 pmid: 35476460 |
|
(r) Liu, X.-J.; Zhang, W.-Y.; Zheng, C.; You, S.-L. Angew. Chem. Int. Ed. 2022, 61, e2022001.
pmid: 35476460 |
|
(s) Moghadam, F. A.; Hicks, E. F.; Sercel, Z. P.; Cusumano, A. Q.; Bartberger, M. D.; Stoltz, B. M. J. Am. Chem. Soc. 2022, 144, 7983.
doi: 10.1021/jacs.2c02960 pmid: 35476460 |
|
(t) Yang, P.; Wang, R.-X.; Cheng, Y.-Z.; Zheng, C.; You, S.-L. Angew. Chem. Int. Ed. 2022, 61, e202213520.
pmid: 35476460 |
|
(u) Yang, W.-L.; Shang, X.-Y.; Luo, X.; Deng, W.-P. Angew. Chem. Int. Ed. 2022, 61, e202203661.
pmid: 35476460 |
|
(v) Jiang, R.; Zhao, Q.-R.; Zheng, C.; You, S.-L. Nat. Catal. 2022, 5, 1089.
doi: 10.1038/s41929-022-00879-z pmid: 35476460 |
|
(w) Zhang, J.; Yang, W.-L.; Zheng, H.; Wang, Y.; Deng, W.-P. Angew. Chem. Int. Ed. 2022, 61, e202117079.
pmid: 35476460 |
|
(x) Wu, Z.-H.; Wang, H.-Y.; Yang, H.-L.; Wei, L.-H.; Hayashi, T.; Duan, W.-L. Angew. Chem. Int. Ed. 2022, 61, e202213904.
pmid: 35476460 |
|
(y) Yang, W.-L.; Shang, X.-Y.; Ni, T.; Yan, H.; Luo, X.; Zhen, H.; Li, Z.; Deng, W.-P. Angew. Chem. Int. Ed. 2022, 61, e202210207.
pmid: 35476460 |
|
(z) Fu, C.; Xiong, Q.; Xiao, L.; He, L.; Bai, T.; Zhang, Z.; Dong, X.-Q.; Wang, C.-J. Chin. J. Chem. 2022, 40, 1059.
doi: 10.1002/cjoc.v40.9 pmid: 35476460 |
|
(aa) Tang, X.; Su, Z.; Lin, Q.; Lin, L.; Dong, S.; Feng, X. Chin. J. Chem. 2022, 40, 1793.
doi: 10.1002/cjoc.v40.15 pmid: 35476460 |
|
(ab) Jia, S.-H.; Chen, S.-Y.; Liu, Z.-S.; Cheng, H.-G.; Zhou, Q.-H. Chin. J. Org. Chem. 2022, 42, 3373. (in Chinese)
doi: 10.6023/cjoc202209002 pmid: 35476460 |
|
(贾仕虎, 陈思元, 刘泽水, 程鸿刚, 周强辉, 有机化学, 2022, 42, 3373.)
doi: 10.6023/cjoc202209002 pmid: 35476460 |
|
(ac) Xie, J.-H.; Hou, Y.-M.; Feng, Z.; You, S.-L. Angew. Chem. Int. Ed. 2023, 63, e202216396.
pmid: 35476460 |
|
[9] |
Liu, X.-J.; Zheng, C.; Yang, Y.-H.; Jin, S.; You, S.-L. Angew. Chem. Int. Ed. 2019, 58, 10493.
doi: 10.1002/anie.v58.31 |
[10] |
(a) Seppanen, O.; Aikonen, S.; Muuronen, M.; Alamillo-Ferrer, C.; Bures, J.; Helaja, J. Chem. Commun. 2020, 56, 14697.
doi: 10.1039/D0CC05999D |
(b) Yang, G.; Ke, Y.-M.; Zhao., Y. Angew. Chem. Int. Ed. 2021, 60, 12775.
doi: 10.1002/anie.v60.23 |
|
(c) Ma, Y.; Ali, H. S.; Hussein, A. A. Catal. Sci. Technol. 2022, 12, 674.
doi: 10.1039/D1CY01617B |
|
[11] |
(a) Kim, U. B.; Jung, D. J.; Jeon, H. J.; Rathwell, K.; Lee, S. Chem. Rev. 2020, 120, 13382.
doi: 10.1021/acs.chemrev.0c00245 |
(b) Wei, L.; Wang, C.-J. Chem Catal. 2023, 3, 100455.
|
[1] | Peng Tao, Xiaokang Zheng, Guoliang Wang, Xinghao Sheng, He Jiang, Wentao Li, Jibiao Jin, Sui-Hung Wong, Yanqin Miao, Hua Wang, Wai-Yeung Wong. Novel Bipolar Orange Emissive Iridium(III) Complexes: Design, Synthesis, and Electroluminescence★ [J]. Acta Chimica Sinica, 2023, 81(8): 891-897. |
[2] | Jianghao Luo, Haowen Ma, Jiehao Zhang, Wei Zhou, Qian Cai. Synthesis of Pyrrolo[3,2-d]pyrimidin-4-ones via Cascade Alkyne−isocyanide [3+2] Cycloaddition/Boulton-Katritzky Rearrangement/Ring Expansion Process★ [J]. Acta Chimica Sinica, 2023, 81(8): 898-904. |
[3] | Xinpu Fu, Xiuling Wang, Weiwei Wang, Rui Si, Chunjiang Jia. Fabrication and Mechanism Study of Clustered Au/CeO2 Catalyst for the CO Oxidation Reaction★ [J]. Acta Chimica Sinica, 2023, 81(8): 874-883. |
[4] | Zhanglong Yu, Zhongliang Li, Changjiang Yang, Qiangshuai Gu, Xinyuan Liu. Research Progress on Copper-Catalyzed Enantioselective Desymmetrization of Diols★ [J]. Acta Chimica Sinica, 2023, 81(8): 955-966. |
[5] | Shuang Yang, Ningyi Wang, Qingqing Hang, Yuchen Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Involving o-Hydroxyphenyl Substituted p-Quinone Methides★ [J]. Acta Chimica Sinica, 2023, 81(7): 793-808. |
[6] | Qingduan Meng, Jiahong Han, Yixiao Pan, Wei Hao, Qing-Hua Fan. Asymmetric Synthesis of C1-Symmetric Chiral N-Heterocyclic Carbene (NHC) Ligands and Their Applications in Asymmetric Catalysis★ [J]. Acta Chimica Sinica, 2023, 81(10): 1271-1279. |
[7] | Lai Zhang, Jian Xiao, Yawen Wang, Yu Peng. Recent Advances on the Construction of Chiral Dihydrobenzofurans by Asymmetric [3+2] Cyclization Reactions of Phenols (Quinones) and Alkenes [J]. Acta Chimica Sinica, 2022, 80(8): 1152-1164. |
[8] | Jinyue Ma, Lufei Huang, Baowen Zhou, Lin Yao. Construction and Catalysis Advances of Inorganic Chiral Nanostructures [J]. Acta Chimica Sinica, 2022, 80(11): 1507-1523. |
[9] | Qing-Ru Zhao, Ru Jiang, Shu-Li You. Ir-catalyzed Sequential Asymmetric Allylic Substitution/Olefin Isomerization for the Synthesis of Axially Chiral Compounds [J]. Acta Chimica Sinica, 2021, 79(9): 1107-1112. |
[10] | Pusu Yang, Chen-Xu Liu, Wen-Wen Zhang, Shu-Li You. Ir-Catalyzed Enantioselective Friedel-Crafts Type Allylic Substitution of Indolizines [J]. Acta Chimica Sinica, 2021, 79(6): 742-746. |
[11] | Bo-Shuai Mu, Zhi-Hao Zhang, Wen-Biao Wu, Jin-Sheng Yu, Jian Zhou. Recent Advances in Synthesis of Chiral 1,2-Dihydropyridines [J]. Acta Chimica Sinica, 2021, 79(6): 685-693. |
[12] | Yijun Guo, Bing Wei, Xiang Zhou, Dongbao Yao, Haojun Liang. DNA Walker-Programmed Nanoparticle Superlattice [J]. Acta Chimica Sinica, 2021, 79(2): 192-199. |
[13] | Yi Li, Ming-Hua Xu. Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines [J]. Acta Chimica Sinica, 2021, 79(11): 1345-1359. |
[14] | Jinhua Li, Qingde Zhuo, Kaiyue Zhuo, Dafa Chen, Haiping Xia. Synthesis and Reactivity Studies of Irida-carbolong Complexes [J]. Acta Chimica Sinica, 2021, 79(1): 71-80. |
[15] | Jin Fengming, Dong Hongwei, Zhao Yan, Zhuang Shengli, Liao Lingwen, Yan Nan, Gu Wanmiao, Zha Jun, Yuan Jinyun, Li Jin, Deng Haiteng, Gan Zibao, Yang Jinlong, Wu Zhikun. Module Replacement of Gold Nanoparticles by a Pseudo-AGR Process [J]. Acta Chimica Sinica, 2020, 78(5): 407-411. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||