Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 276-283.DOI: 10.6023/cjoc202007046 Previous Articles Next Articles
Article
收稿日期:
2020-07-19
修回日期:
2020-08-17
发布日期:
2020-09-09
通讯作者:
高先池, 杨勇
作者简介:
基金资助:
Jianing Chea, Tao Songb, Xianchi Gaoa,*(), Yong Yangb,*()
Received:
2020-07-19
Revised:
2020-08-17
Published:
2020-09-09
Contact:
Xianchi Gao, Yong Yang
Supported by:
Share
Jianing Che, Tao Song, Xianchi Gao, Yong Yang. Borrowing Hydrogen Reductive Coupling of Nitroarenes with Benzyl Alcohols to Imines Catalyzed by Pd Nanoparticles on N Doped Carbon Materials[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 276-283.
Entry | Solvent | Base (equiv.) | Conv. b /% | 3a b /% | 4a b /% |
---|---|---|---|---|---|
1 | Toluene | t-BuOK (2.5) | 59 | 59 | 60 |
2 | Toluene | t-BuOK (3.0) | 100 | >99 | 0 |
3 c | Toluene | t-BuOK (3.0) | 100 | >99 | 0 |
4 c | Toluene | t-BuOK (4.0) | 100 | 0 | >99 |
5 | Toluene | KHMDS (3.0) | 100 | 40 | 60 |
6 | Toluene | NaOH (3.0) | 32 | 24 | 8 |
7 | Toluene | Na2CO3(3.0) | 0 | 0 | 0 |
8 d | Toluene | t-BuOK (3.0) | 100 | >99 | 0 |
9 e | Toluene | t-BuOK (3.0) | 100 | >99 | 0 |
10 f 11 g | Toluene Toluene | t-BuOK (3.0) t-BuOK (3.0) | 63 40 | 63 40 | 0 0 |
12 d | 2-Methyl-THF | t-BuOK (3.0) | 86 | 9 | 1 |
13 d | Dioxane | t-BuOK (3.0) | 38 | 17 | 0 |
13 d | CH3CN | t-BuOK (3.0) | 100 | 0 | 0 |
14 d | n-Hexane | t-BuOK (3.0) | 51 | 23 | 0 |
Entry | Solvent | Base (equiv.) | Conv. b /% | 3a b /% | 4a b /% |
---|---|---|---|---|---|
1 | Toluene | t-BuOK (2.5) | 59 | 59 | 60 |
2 | Toluene | t-BuOK (3.0) | 100 | >99 | 0 |
3 c | Toluene | t-BuOK (3.0) | 100 | >99 | 0 |
4 c | Toluene | t-BuOK (4.0) | 100 | 0 | >99 |
5 | Toluene | KHMDS (3.0) | 100 | 40 | 60 |
6 | Toluene | NaOH (3.0) | 32 | 24 | 8 |
7 | Toluene | Na2CO3(3.0) | 0 | 0 | 0 |
8 d | Toluene | t-BuOK (3.0) | 100 | >99 | 0 |
9 e | Toluene | t-BuOK (3.0) | 100 | >99 | 0 |
10 f 11 g | Toluene Toluene | t-BuOK (3.0) t-BuOK (3.0) | 63 40 | 63 40 | 0 0 |
12 d | 2-Methyl-THF | t-BuOK (3.0) | 86 | 9 | 1 |
13 d | Dioxane | t-BuOK (3.0) | 38 | 17 | 0 |
13 d | CH3CN | t-BuOK (3.0) | 100 | 0 | 0 |
14 d | n-Hexane | t-BuOK (3.0) | 51 | 23 | 0 |
Entry | [Pd] | Con./% | 3a/% | 4a/% |
---|---|---|---|---|
1 | Pd/AC | 66 | 6 | 60 |
2 | Pd/Al2O3 | 21 | 18 | 3 |
3 | Pd/TiO2 | 100 | 69 | 31 |
4 | Pd/ZrO2 | 81 | 72 | 9 |
5 | Pd/CeO2 | 68 | 55 | 13 |
6 | Pd/MgO | 30 | 28 | 2 |
7 | Pd/g-C3N4 | 89 | 73 | 16 |
Entry | [Pd] | Con./% | 3a/% | 4a/% |
---|---|---|---|---|
1 | Pd/AC | 66 | 6 | 60 |
2 | Pd/Al2O3 | 21 | 18 | 3 |
3 | Pd/TiO2 | 100 | 69 | 31 |
4 | Pd/ZrO2 | 81 | 72 | 9 |
5 | Pd/CeO2 | 68 | 55 | 13 |
6 | Pd/MgO | 30 | 28 | 2 |
7 | Pd/g-C3N4 | 89 | 73 | 16 |
[1] |
Adams, J.P. J. Chem. Soc., Perkin Trans. 1 2000, 125.
|
Hadjipavlou-Litina, D.J.; Geronikaki, A.A. Drug Des. Discovery 1998, 15, 199.
|
|
[2] |
Su, F.; Mathew, S.C.; Mohlmann, L.; Antonietti, M; Wang, X.; Blechert, S. Angew. Chem., Int. Ed. 2012, 51, 657.
|
Largeron, M.; Feury, M.-B. Angew. Chem., Int. Ed. 2011, 50, 5409.
|
|
Schümperli, M.T.; Hammond, C.; Hermans, I. ACS Catal. 2012, 2, 1108.
|
|
Biswas, S.; Dutta, B.; Mullick, K.; Kuo, C.H.; Poyraz, A.S.; Suib, S.L. ACS Catal. 2015, 5, 4394.
|
|
Yuan, H.; Yoo, W.-J.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc. 2012, 134, 13970.
|
|
Chen, B.; Wang, L.-Y.; Gao, S. ACS. Catal. 2015, 5, 5851.
|
|
Geng, L.L.; Song, J.J.; Zheng, B.; Wu, S.J.; Zhang, W.X.; Jia, M.J.; Liu, G. Chin. J. Catal. 2016, 37, 1451.
|
|
Tamura, M.; Tomishige, K. Angew. Chem., Int. Ed. 2015, 54, 864.
|
|
Liu, D; Zhang, C.H.; Du, M.M.; Zhang, X.L.; Zhao, P.S.; Yang, P. Chin. J. Org. Chem. 2018, 38, 1350.
|
|
(刘迪, 张成慧, 韩楠, 杜萌萌, 张效露, 赵朋杉, 杨萍, 有机化学, 2018, 38, 1350.).
|
|
[3] |
Corma, A.; Navas, J.; Sabater, M.J. Chem. Rev. 2018, 118, 1410.
|
Obora, Y. ACS Catal. 2014, 4, 3972.
|
|
Guillena, G.; Ramon, D.; Yus, M. Chem. Rev. 2010, 110, 1611.
|
|
[4] |
Das, K.; Shibuya, R.; Nakahara, Y.; Germain, N.; Ohshima, T.; Mashima, K. Angew. Chem., Int. Ed. 2012, 51, 150.
|
Dang, T.T.; Ramalingam, B.; Shan, S.P.; Seayad, A.M. ACS Catal. 2013, 3, 2536.
|
|
Maji, M.; Chakrabarti, K.; Paul, B.; Roy, B.C.; Kundu, S. Adv. Synth. Catal. 2018, 360, 722.
|
|
Imm, S.; Bahn, S.; Neubert, L.; Neumann, H.; Beller M.Angew. Chem. Int. Ed. 2010, 49, 8126.
|
|
Pingen, D.; Müller, C.; Vogt, D. Angew. Chem., Int. Ed. 2010, 49, 8130.
|
|
Cano, R.; Ramon, D.J.; Yus, M. J. Org. Chem. 2011, 76, 5547.
|
|
Hamid, M.H.S. A.; Allen, C.L.; Lamb, G.W.; Maxwell, A.C.; Maytum, H.C.; Watson, A.J.A.; Williams, J.M.J.J. Am. Chem. Soc. 2009, 131, 1766.
|
|
Kawahara, R.; Fujita, K.-I.; Yama-guchi, R. J. Am. Chem. Soc. 2010, 132, 15108.
|
|
Ruch, S.; Irrgang, T.; Kempe, R. Chem. -Eur. J. 2014, 20, 13279.
|
|
Saidi, O.; Blacker, A.J.; Farah, M.M.; Marsden, S.P.; Williams, J.M.J. Chem. Commun. 2010, 46, 1541.
|
|
Gunanathan, C.; Milstein, D. Angew. Chem., Int. Ed. 2008, 47, 8661.
|
|
Yan, T.; Feringa, B.L.; Barta, K. Nat. Commun. 2014, 5, 5602.
|
|
Rawlings, A.J.; Diorazio, L.J.; Wills, M. Org. Lett. 2015, 17, 1086.
|
|
Mukherjee, A.; Nerush, A.; Leitus, G.; Shimon, L.J.W.; David, Y.B.; Jalapa, N.A.E.; Milstein, D. J. Am. Chem. Soc. 2016, 138, 4298.
|
|
Elangovan, S.; Neumann, J.; Sortais, J.-B.; Junge, K.; Darce, C.; Beller M.Nat. Commun. 2016, 7, 12641.
|
|
Rosler, S.; Ertl, M.; Irrgang, T.; Kempe, R. Angew. Chem., Int. Ed. 2015, 54, 15046.
|
|
Mastalir, M.; Tomsu, G.; Pittenauer, E.; Allmaier, G.; Kirchner, K. Org. Lett. 2016, 18, 3462.
|
|
Lu, X.L.; Zhang, L.; Gu, X.L.; Liu, Y.X. Fine Chem. 2013, 44, 29.
|
|
(r) Yang, P.; Liu, M.; Zhang, H.; Guo, W.; Lv, C.; Liu, D. Prog. Chem. 2020, 32, 72.
|
|
[5] |
Tang, L.; Sun, H.; Li, Y.; Zha, Z.; Wang, Z. Green Chem. 2012, 14, 3423.
|
Chen, J.; Huang, S.; Lin, J.; Su, W. Appl. Catal. A 2014, 470, 1.
|
|
[6] |
J. J. G. J.; Duan, Y. N.; Zhang, S. C.; Fei, B. H.; Chen, X. F.; Yang, Y.ChemSusChem 2017, 10, 3427.
|
Duan, Y. N.; Ji, G. J.; Zhang, S. C.; Chen, X. F.; Yang, Y.Catal. Sci. Technol. 2018, 8, 1039.
|
|
[7] |
Ji, G.J. ; Duan, Y.N. ; Zhang, S.C. Yang, Y. Catal. Today 2019 , 15 , 101.
|
[8] |
Song, T. ; Duan, Y. ; Yang, Y. Catal. Commun . 2019 , 120 , 80.
|
[9] |
Yu, L.; Huang, Y.; Wei, Z.; Ding, Y.; Su, C.; Xu, Q. J. Org. Chem. 2015, 80, 8677.
|
Zhang, D.; Wei, Z.; Yu, L. Sci. Bull. 2017, 62, 1325.
|
|
[10] |
Chen, Y.; Jing, X.; Yu, L. Chin. J. Org. Chem. , 2020, 40, 2570.
|
(陈颖, 景崤壁, 俞磊, 有机化学, 2020, 40, 2570.).
|
|
Chen, Y.; Zhang, Q.; Jing, X.; Han, J.; Yu, L. Mater. Lett. 2019, 242, 170.
|
|
Zhang, D.; Deng, X.; Zhang, Q.; Yu, L. Mater. Lett. 2019, 234, 216.
|
|
[11] |
Song, T. ; Duan, Y. ; Chen, X. ; Yang, Y. Catalysts 2019 , 9 , 116.
|
[12] |
Mohamad, T. ; Moomen, B. ; Fawaz, E. ; Amer, E. ; Mazen, E. ; Valerie, R. Asian J. Chem . 2006 , 18 , 1771.
|
[13] |
Roe, A. ; Montgomery, J.A. J. Am. Chem. Soc . , 1953 , 75 , 910.
|
[14] |
Torregros, R. ; Pastor, I.M. ; Yus, M. Tetrahedron 2005 , 61 , 11148.
|
[15] |
Benington, F. ; Morin, R.D. ; Clark, Leland, C., Jr. J. Org. Chem . 1958 , 23 , 19.
|
[16] |
Maginnity, P.M. ; Eisenmann, J.L. J. Am. Chem. Soc . 1952 , 74 , 6119.
|
[17] |
Hartley, J.H. ; Phillips, M.D. ; James, T.D. New J. Chem . , 2002 , 26 , 1228.
|
[18] |
Bennett, J.S. ; Charles, K.L. ; Miner, M.R. ; Heuberger, C.F. ; Spina, E.J. ; Bartels, M.F. ; Foreman, T. Green Chem . 2009 , 11 , 166.
|
[19] |
Steevens, J.B. ; Pandit, U.K. Tetrahedron 1983 , 39 , 1395.
|
[1] | Hu Ma, Danfeng Huang, Kehu Wang, Duoduo Tang, Yang Feng, Yuanyuan Reng, Junjiao Wang, Yulai Hu. Synthesis of 3-Trifluoromethylpyrazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3257-3267. |
[2] | Yongling Wang, Tiexin Zhang, Xuming Zhang, Hanyang Sun, Jinyao Leng, Yaming Li. Synthesis of Unnatural Amino Acid Derivatives by Visible- Light-Catalyzed Decarboxylative Alkylation of N-Aromatic Glyoxylimines [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4284-4293. |
[3] | Xuechun Zhao, Hui Fan, Yao Xu, Xiaoming Liao, Xiaoxiang Zhang. PPh3-Mediated Synthesis of 3-Hydroxy-2-oxindoles from o-Alkynylnitrobenzenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3997-4002. |
[4] | Limei Xu, Linyan Lu, Jinzhong Cai, Yadong Feng, Xiuling Cui. Construction of Diaminobenzoquinone Imines through Radical Coupling of Aminophenols with Amine under UV-Light [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1210-1215. |
[5] | Jiahao Li, Hongqiang Liu, Bo Zhang, Bingyang Ge, Dawei Wang. Synthesis of Supported Indazolyl-Pyridyl-Quinoline Iridium Catalyst and Its Application to N-Alkylation of 2-Aminobenzothiazoles [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 619-630. |
[6] | Jiahao Li, Yike Yang, Wenkang Hu, Xiaofeng Xia, Dawei Wang. Catalytic Synthesis of Pyrazine and Ketone Derivatives by Unsymmetrical Triazolyl-Naphthyridinyl-Pyridine Copper [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 190-199. |
[7] | Linlin Li, Xiaoyu Chen, Congcong Pei, Jingya Li, Dapeng Zou, Yangjie Wu, Yusheng Wu. Transition Metal-Free Deuteride Reduction of N-tert-Butanesulfinyl Ketimines Derivatives via B2pin2/D2O System [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2319-2325. |
[8] | Zhang Yongna, Duan Hui-Xin, Wang You-Qing. Research Progress in Asymmetric Reactions of Imines Using Chiral Primary Amines as Organocatalysts [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1514-1528. |
[9] | Cao Zhicheng, Liu Jianchao, Chu Youqun, Zhao Fengming, Zhu Yinghong, She Yuanbin. Paired Electro-synthesis of Aryl Nitriles [J]. Chin. J. Org. Chem., 2019, 39(9): 2499-2506. |
[10] | Chen Xun, Bai Lili, Zeng Wei. Recent Advances in C-H Bond Functionalization/Cyclization Involving Imines [J]. Chin. J. Org. Chem., 2018, 38(8): 1859-1871. |
[11] | Wang Yuchao, Ye Qiuxiang, Qiu Guanyinsheng, Liu Jin-Biao. Recent Advances in Transition Metal-Catalyzed Denitration-Coupling of Nitroarenes [J]. Chin. J. Org. Chem., 2018, 38(7): 1650-1655. |
[12] | Liu Di, Zhang Chenghui, Han Nan, Du Mengmeng, Zhang Xiaolu, Zhao Pengshan, Yang Ping. Progress in Oxidative Coupling of Amines to Imines [J]. Chin. J. Org. Chem., 2018, 38(6): 1350-1363. |
[13] | Xu Huan, Zhang Maoyuan, Huang Xiang, Shi Dabin. Palladium Nanoparticles Supported on MIL-101 as an Efficient Heterogeneous Catalyst for Selective C2 Arylation of Benzofuran [J]. Chin. J. Org. Chem., 2018, 38(4): 832-839. |
[14] | Fu Yufang, Zou Zhijuan, Tang Cheng, Song Kunpeng. A Red Bayberry Shape Monodisperse Microsphere Support Pd Nanoparticles for Suzuki-Miyaura Cross-Coupling Reaction at Room Temperature [J]. Chin. J. Org. Chem., 2018, 38(11): 3106-3111. |
[15] | Sokolov Viacheslav I.. Synthesis and Application of N-Cyclopalladated Ferrocene Derivatives [J]. Chin. J. Org. Chem., 2018, 38(1): 75-85. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||