Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (9): 2889-2897.DOI: 10.6023/cjoc202404018 Previous Articles Next Articles
ARTICLES
杜佳言a,b, 刘俊涛b,c, 刘桂霞b,*(), 黄正b,c,*()
收稿日期:
2024-04-12
修回日期:
2024-05-06
发布日期:
2024-05-10
通讯作者:
刘桂霞, 黄正
作者简介:
基金资助:
Jiayan Dua,b, Juntao Liub,c, Guixia Liub(), Zheng Huangb,c()
Received:
2024-04-12
Revised:
2024-05-06
Published:
2024-05-10
Contact:
Guixia Liu, Zheng Huang
About author:
Supported by:
Share
Jiayan Du, Juntao Liu, Guixia Liu, Zheng Huang. Cobalt-Catalyzed Regio- and Stereoselective Isomerization of Terminal Alkenes to trans-2-Alkenes[J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2889-2897.
Entry | [Co] | Solvent | Time/h | Conv./% | Yield/% of 2a (E∶Z) | Yield/% of 3- or 4-octene |
---|---|---|---|---|---|---|
1 | 3a | THF | 1 | 42 | 41 (9∶1) | 1 |
2 | 3a | Hexane | 1 | 97 | 92 (4∶1) | 5 |
3 | 3a | Toluene | 1 | 97 | 88 (6∶1) | 9 |
4 | 3a | CH3CN | 1 | 0 | ||
5 | 3a | Diethyl ether | 1 | 67 | 65 (11∶1) | 2 |
6 | 3a | Diethyl ether | 2 | 78 | 76 (11∶1) | 2 |
7 | 3a | Diethyl ether | 2.75 | 98 | 93 (11∶1) | 5 |
8 | 3a | Diethyl ether | 3 | 98 | 80 (8∶1) | 18 |
9 | 3a | Diethyl ether | 24 | 99 | 69 (6∶1) | 30 |
10 | 3b | Diethyl ether | 2.75 | 45 | 45 (10∶1) | 0 |
11 | 3c | Diethyl ether | 2.75 | 0 |
Entry | [Co] | Solvent | Time/h | Conv./% | Yield/% of 2a (E∶Z) | Yield/% of 3- or 4-octene |
---|---|---|---|---|---|---|
1 | 3a | THF | 1 | 42 | 41 (9∶1) | 1 |
2 | 3a | Hexane | 1 | 97 | 92 (4∶1) | 5 |
3 | 3a | Toluene | 1 | 97 | 88 (6∶1) | 9 |
4 | 3a | CH3CN | 1 | 0 | ||
5 | 3a | Diethyl ether | 1 | 67 | 65 (11∶1) | 2 |
6 | 3a | Diethyl ether | 2 | 78 | 76 (11∶1) | 2 |
7 | 3a | Diethyl ether | 2.75 | 98 | 93 (11∶1) | 5 |
8 | 3a | Diethyl ether | 3 | 98 | 80 (8∶1) | 18 |
9 | 3a | Diethyl ether | 24 | 99 | 69 (6∶1) | 30 |
10 | 3b | Diethyl ether | 2.75 | 45 | 45 (10∶1) | 0 |
11 | 3c | Diethyl ether | 2.75 | 0 |
[1] |
Wang, E.-J. Stereoselective Alkene Synthesis, Springer-Verlag, 2012.
|
[2] |
Takeda, T.; Tsubouchi, A. Org. React. 2013, 82, 1.
|
[3] |
Holland, P. L. Acc. Chem. Res. 2015, 48, 1696.
|
[4] |
Hilt, G. ChemCatChem 2014, 6, 2484.
|
[5] |
Yu, X.; Zhao, H.; Li, P.; Koh, M. J. J. Am. Chem. Soc. 2020, 142, 18223.
|
[6] |
Kapat, A.; Sperger, T.; Guven, S.; Schoenebeck, F. Science 2019, 363, 391.
doi: 10.1126/science.aav1610 pmid: 30679370 |
[7] |
Garhwal, S.; Kaushansky, A.; Fridman, N.; De Ruiter, G. Chem Catal. 2021, 1, 631.
|
[8] |
(a) Ge, Q.; Meng, J.; Liu, H.; Yang, Z.; Wu, Z.; Zhang, W. Chin. J. Chem. 2022, 40, 2269.
|
(b) Ren, W.; Sun, F.; Chu, J.; Shi, Y. Org. Lett. 2020, 22, 1868.
|
|
(c) Thiery, E.; Chevrin, C.; Le Bras, J.; Harakat, D.; Muzart, J. J. Org. Chem. 2007, 72, 1859.
|
|
(d) Gauthier, D.; Lindhardt, A. T.; Olsen, E. P. K.; Overgaard, J.; Skrydstrup, T. J. Am. Chem. Soc. 2010, 132, 7998.
|
|
(e) Chen, C.; Hou, C.; Chen, P.; Liu, G. Chin. J. Chem. 2020, 38, 346.
|
|
[9] |
(a) Wang, Y.; Qin, C.; Jia, X.; Leng, X.; Huang, Z. Angew. Chem. Int. Ed. 2017, 56, 1614.
|
(b) Camp, A. M.; Kita, M. R.; Blackburn, P. T.; Dodge, H. M.; Chen, C.-H.; Miller, A. J. M. J. Am. Chem. Soc. 2021, 143, 2792.
|
|
[10] |
(a) Larsen, C. R.; Grotjahn, D. B. J. Am. Chem. Soc. 2012, 134, 10357.
doi: 10.1021/ja3036477 pmid: 24422470 |
(b) Larsen, C. R.; Erdogan, G.; Grotjahn, D. B. J. Am. Chem. Soc. 2014, 136, 1226.
doi: 10.1021/ja411438d pmid: 24422470 |
|
(c) Donohoe, T. J.; O'riordan, T. J. C.; Rosa, C. P. Angew. Chem. Int. Ed. 2009, 48, 1014.
pmid: 24422470 |
|
(d) Trost, B. M.; Cregg, J. J.; Quach, N. J. Am. Chem. Soc. 2017, 139, 5133.
pmid: 24422470 |
|
(e) Lai, Y.; Dai, W.-M. Chin. J. Chem. 2021, 39, 69.
pmid: 24422470 |
|
(f) Zhao, L.; Wang, X.; Qiang, Q.; Zhao, X.; Liu, F.; Lu, S.; Rong, Z.-Q. Chin. J. Chem. 2024, 42, 1828.
pmid: 24422470 |
|
[11] |
(a) Tanaka, K.; Qiao, S.; Tobisu, M.; Lo, M. M. C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 9870.
pmid: 26756445 |
(b) Martínez, J. I.; Smith, J. J.; Hepburn, H. B.; Lam, H. W. Angew. Chem. Int. Ed. 2016, 55, 1108.
doi: 10.1002/anie.201508964 pmid: 26756445 |
|
(c) Qin, A.; Zhang, Q.; Qian, H.; Han, Y.; Ma, S. Chin. J. Chem. 2021, 39, 559.
pmid: 26756445 |
|
[12] |
(a) Liu, X.; Li, B.; Liu, Q. Synthesis 2019, 51, 1293.
|
(b) Xu, S.; Liu, G.; Huang, Z. Chin. J. Chem. 2021, 39, 585.
|
|
(c) Zhang, M.; Ji, Y.; Zhang, C. Chin. J. Chem. 2022, 40, 1608.
|
|
(d) Zhang, Z.; Butt, N. A.; Zhou, M.; Liu, D.; Zhang, W. Chin. J. Chem. 2018, 36, 443.
|
|
(e) Chen, J.; Guo, J.; Lu, Z. Chin. J. Chem. 2018, 36, 1075.
|
|
(f) Li, Y.; Lu, X.; Fu, Y. CCS Chem. 2024, 6, 1130.
|
|
(g) Wu, L.; We, H.-L.; Shen, J.-F.; Chen, J.-Z.; Zhang, W.-B. Acta Chim. Sinica 2021, 79, 1331 (in Chinese).
|
|
(吴良, 魏瀚林, 申杰峰, 陈建中, 张万斌, 化学学报, 2021, 79, 1331.)
doi: 10.6023/A21070338 |
|
[13] |
(a) Crossley, S. W. M.; Barabé, F.; Shenvi, R. A. J. Am. Chem. Soc. 2014, 136, 16788.
doi: 10.1021/ja5105602 pmid: 25398144 |
(b) Li, G.; Kuo, J. L.; Han, A.; Abuyuan, J. M.; Young, L. C.; Norton, J. R.; Palmer, J. H. J. Am. Chem. Soc. 2016, 138, 7698.
pmid: 25398144 |
|
(c) Liu, X.; Zhang, W.; Wang, Y.; Zhang, Z. X.; Jiao, L.; Liu, Q. J. Am. Chem. Soc. 2018, 140, 6873.
pmid: 25398144 |
|
(d) Zhang, S.; Bedi, D.; Cheng, L.; Unruh, D. K.; Li, G.; Findlater, M. J. Am. Chem. Soc. 2020, 142, 8910.
pmid: 25398144 |
|
(e) Zhao, J.; Cheng, B.; Chen, C.; Lu, Z. Org. Lett. 2020, 22, 837.
pmid: 25398144 |
|
(f) Liu, H.; Cai, C.; Ding, Y.; Chen, J.; Liu, B.; Xia, Y. ACS Omega 2020, 5, 11655.
pmid: 25398144 |
|
[14] |
(a) Pünner, F.; Schmidt, A.; Hilt, G. Angew. Chem. Int. Ed. 2012, 51, 1270.
pmid: 24386941 |
(b) Schmidt, A.; Nödling, A. R.; Hilt, G. Angew. Chem. Int. Ed. 2015, 54, 801.
pmid: 24386941 |
|
(c) Chen, C.; Dugan, T. R.; Brennessel, W. W.; Weix, D. J. Holland, P. L. J. Am. Chem. Soc. 2014, 136, 945.
doi: 10.1021/ja408238n pmid: 24386941 |
|
(d) Kim, D.; Pillon, G.; Diprimio, D. J.; Holland, P. L. J. Am. Chem. Soc. 2021, 143, 3070.
pmid: 24386941 |
|
[15] |
Kobayashi, T.; Yorimitsu, H.; Oshima, K. Chem. Asian. J. 2009, 4, 1078.
|
[16] |
Meng, Q.-Y.; Schirmer, T. E.; Katou, K.; König, B. Angew. Chem. Int. Ed. 2019, 58, 5723.
|
[17] |
Liu, J.; Du, J.; Yu, F.; Gan, L.; Liu, G.; Huang, Z. ACS Catal. 2023, 13, 7995.
|
[18] |
Molloy, J. J.; Morack, T.; Gilmour, R. Angew. Chem. Int. Ed. 2019, 58, 13654.
doi: 10.1002/anie.201906124 pmid: 31233259 |
[19] |
Massad, I.; Marek, I. ACS Catal. 2020, 10, 5793.
|
[20] |
Biswas, S.; Huang, Z.; Choliy, Y.; Wang, D. Y.; Brookhart, M.; Krogh-Jespersen, K.; Goldman, A. S. J. Am. Chem. Soc. 2012, 134, 13276.
|
[21] |
Iwasaki, K.; Wan, K. K.; Oppedisano, A.; Crossley, S. W. M.; Shenvi, R. A. J. Am. Chem. Soc. 2014, 136, 1300.
doi: 10.1021/ja412342g pmid: 24428640 |
[22] |
Obradors, C.; Martinez, R. M.; Shenvi, R. A. J. Am. Chem. Soc. 2016, 138, 4962.
doi: 10.1021/jacs.6b02032 pmid: 26984323 |
[23] |
Rubel, C. Z.; Ravn, A. K.; Ho, H. C.; Yang, S.; Li, Z.-Q.; Engle, K. M.; Vantourout, J. C. Angew. Chem. Int. Ed. 2024, e202320081.
|
[24] |
(a) Li, X.-R.; Zhang, R.-J.; Xiao, Y.; Tong, Q.-X.; Zhong, J.-J. Org. Chem. Front. 2024, 11, 646.
|
(b) Zhang, R.-J.; Li, X.-R.; Liang, R.-B.; Xiao, Y.; Tong, Q.-X.; Zhong, J.-J.; Wu, L.-Z. Org. Lett. 2024, 26, 591.
|
|
[25] |
Kawamura, K. E.; Chang, A. S.-M.; Martin, D. J.; Smith, H. M.; Morris, P. T.; Cook, A. K. Organometallics 2022, 41, 486.
|
[26] |
Liu, H.; Xu, M.; Cai, C.; Chen, J.; Gu, Y.; Xia, Y. Org. Lett. 2020, 22, 1193.
|
[27] |
Movassaghi, M.; Ahmad, O. K. Angew. Chem. Int. Ed. 2008, 47, 8909.
doi: 10.1002/anie.200802921 pmid: 18924200 |
[1] | Ping Li, Yin Zhang, Zi-Qi Yang, Wen-Juan Hao, Bo Jiang. Base-Promoted Deconstructive Reaction of Exocyclic 1,3-Dicarbonyls for Accessing Hydrazonylated 1,n-Dicarbonyls and Its Biological Evaluation [J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2777-2784. |
[2] | Longlong Li, Xinyue He, Longsheng Zhou, Hengtong Qu, Chengtao Feng, Kun Xu. NH4SCN-Promoted Formal [3+3] Annulation for the Synthesis of 5-Arylated Pyrazolo[1,5-a]pyrimidines [J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2832-2840. |
[3] | Jie Zhu, Sidan Tang, Xiumei Kan, Shizhu Fan, Pengfei Wang, Peijun Yang. Solvent-Controlled Sc(OTf)3-Catalyzed Ring Opening Reaction of 2-(Hetero)aryl-N-sulfonylazetidines: Synthesis of Allylic Amines/1,3-Oxazinane Derivatives [J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2796-2809. |
[4] | Lingyi Lu, Xiaodong Qiu. Recent Progress in Radical Involved Alkene Dialkylation [J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1701-1718. |
[5] | Yuxuan Yan, Wanqing Lu, Huijun Qian, Leiyang Lv, Zhiping Li. Pd-Catalyzed Ring-Opening of gem-Difluorocyclopropanes for the Mono- and Bis-fluoroallylation of 1,3-Dicarbonyls [J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1630-1640. |
[6] | Xiaoyong Li, Danfeng Huang, Yuxiu Zhou, Xiaokang Liu, Kehu Wang, Junjiao Wang, Yulai Hu. [3+2] Cyclization of Difluoroacetohydrazonoyl Bromides with β-(N,N-Dimethylamino)enones/Enoates/Enamides [J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1226-1239. |
[7] | Yatong Fu, Chaofan Sun, Dan Zhang, Chengguo Jin, Juyou Lu. Recent Progress in B—H Bond Functionalization of nido-Carboranes [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 438-447. |
[8] | Jian Zhang, Wanjie Liang, Yi Yang, Fachao Yan, Hui Liu. Regiocontrollable Difunctionalization of N-Allenamines [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 335-348. |
[9] | Jingrui Wang, Yongkui Feng, Nengzhong Wang, Nianyu Huang, Hui Yao. Pd-Catalyzed Stereoselective Synthesis of Nitroalkyl β-C-Glycosides [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3216-3225. |
[10] | Xiaojing Hu, Feixiang Guo, Runqing Zhu, Bingqi Zhou, Tao Zhang, Lizhen Fang. Synthesis of p-Alkoxy Phenol and Its Application after Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2239-2244. |
[11] | Sida Li, Xing-Zhong Shu, Lipeng Wu. Zirconium and Titanium Mediated Hydroboration of Alkenes and Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1751-1760. |
[12] | Shiquan Gao, Chuangjun Liu, Junfeng Yang, Junliang Zhang. Cobalt-Catalyzed Electrochemical Reductive Coupling of Alkynes and Alkenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1559-1565. |
[13] | Jian Ji, Jinhua Liu, Cong Guan, Xuwen Chen, Yun Zhao, Shunying Liu. High Regioselective Synthesis of N2-Substituted-1,2,3-triazole via N-Sulfonyl-1,2,3-triazole Coupling with Alcohol Catalyzed by in-situ Generated Sulfonic Acid [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1168-1176. |
[14] | Xun Xiang, Zhaolin He, Xiuqin Dong. Recent Advances of Efficient Synthesis of Chiral Molecules Promoted by Pd/Chiral Phosphoric Acid Synergistic Catalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 791-808. |
[15] | Kang Pan, Fan Xu. Lanthanum Silylamide-Catalyzed Synthesis of Enol Phosphates [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4261-4267. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||