Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (7): 2492-2498.DOI: 10.6023/cjoc202212025 Previous Articles Next Articles
ARTICLES
范威*(
)
收稿日期:2022-12-19
修回日期:2023-01-22
发布日期:2023-03-17
通讯作者:
范威
基金资助:
Wei Fan()
Received:2022-12-19
Revised:2023-01-22
Published:2023-03-17
Contact:
Wei Fan
Supported by:Share
Wei Fan. O2-Enabled C—H Imination of Five-Membered Cyclic Enamines[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2492-2498.
| Entry | Solvent | Temp./℃ | Yieldb/% |
|---|---|---|---|
| 1 | EA | 100 | 27 |
| 2 | EtOH | 100 | 29 |
| 3 | DCE | 100 | 33 |
| 4 | Benzene | 100 | Trace |
| 5 | 1,4-Dioxane | 100 | 43 |
| 6 | THF | 100 | 58 |
| 7 | MeCN | 100 | 68 |
| 8 | MeCN | 110 | 70 |
| 9 | MeCN | 115 | 71 |
| 10 | MeCN | 120 | 73 |
| 11 | MeCN | 125 | 72 |
| 12 | MeCN | 130 | 71 |
| 13 | MeCN | 120 | 73c |
| 14 | MeCN | 120 | NDd |
| Entry | Solvent | Temp./℃ | Yieldb/% |
|---|---|---|---|
| 1 | EA | 100 | 27 |
| 2 | EtOH | 100 | 29 |
| 3 | DCE | 100 | 33 |
| 4 | Benzene | 100 | Trace |
| 5 | 1,4-Dioxane | 100 | 43 |
| 6 | THF | 100 | 58 |
| 7 | MeCN | 100 | 68 |
| 8 | MeCN | 110 | 70 |
| 9 | MeCN | 115 | 71 |
| 10 | MeCN | 120 | 73 |
| 11 | MeCN | 125 | 72 |
| 12 | MeCN | 130 | 71 |
| 13 | MeCN | 120 | 73c |
| 14 | MeCN | 120 | NDd |
| [1] |
(a) Hadjipavlou-Litina, D. J.; Geronikaki, A. A. Drug Des. Discovery 1998, 15, 199.
pmid: 18850749 |
|
(b) Adams, J. P. J. Chem. Soc., Perkin Trans. 1 2000, 125.
pmid: 18850749 |
|
|
(c) Gawronski, J.; Wascinska, N.; Gajewy, J. Chem. Rev. 2008, 108, 5227.
doi: 10.1021/cr800421c pmid: 18850749 |
|
|
(d) Patil, R. D.; Adimurthy, S. Asian J. Org. Chem. 2013, 2, 726.
doi: 10.1002/ajoc.v2.9 pmid: 18850749 |
|
| [2] |
(a) Eguchi, S. ARKIVOC 2005, 2005, 98.
|
|
(b) Palacios, F.; Alonso, C.; Aparicio, D.; Rubiales, G.; de los Santos, J. M. Tetrahedron 2007, 63, 523.
doi: 10.1016/j.tet.2006.09.048 |
|
|
(c) Palacios, F.; Aparicio, D.; Rubiales, G.; Alonso, C.; de los Santos, J. M. Curr. Org. Chem. 2009, 13, 810.
doi: 10.2174/138527209788167196 |
|
| [3] |
Li, H.; Lupp, D.; Das, P. K.; Yang, L.; Gonçalves, T. P.; Huang, M.-H.; Hajoui, M. E.; Liang, L.-C.; Huang, K.-W. ACS Catal. 2021, 11, 4071.
doi: 10.1021/acscatal.1c00379 |
| [4] |
(a) Ell, A. H.; Samec, J. S. M.; Brasse, C.; Baeckvall, J.-E. Chem. Commun. 2002, 1144.
pmid: 17992680 |
|
(b) Largeron, M.; Chiaroni, A.; Fleury, M.-B. Chem.-Eur. J. 2008, 14, 996.
pmid: 17992680 |
|
|
(c) Jiang, G.; Chen, J.; Huang, J.-S.; Che, C.-M. Org. Lett. 2009, 11, 4568.
doi: 10.1021/ol9018166 pmid: 17992680 |
|
|
(d) Su, F.; Mathew, S. C.; Moehlmann, L.; Antonietti, M.; Wang, X.; Blechert, S. Angew. Chem., Int. Ed. 2011, 50, 657.
pmid: 17992680 |
|
|
(e) Chen, B.; Wang, L.; Gao, S. ACS Catal. 2015, 5, 5851.
doi: 10.1021/acscatal.5b01479 pmid: 17992680 |
|
|
(f) Ray, R.; Chandra, S.; Yadav, V.; Mondal, P.; Maiti, D.; Lahiri, G. K. Chem. Commun. 2017, 53, 4006.
doi: 10.1039/C6CC10200J pmid: 17992680 |
|
| [5] |
(a) Blackburn, L.; Taylor, R. J. K. Org. Lett. 2001, 3, 1637.
pmid: 26924231 |
|
(b) Gnanaprakasam, B.; Zhang, J.; Milstein, D. Angew. Chem., Int. Ed. 2010, 49, 1468.
doi: 10.1002/anie.200907018 pmid: 26924231 |
|
|
(c) Maggi, A.; Madsen, R. Organometallics 2012, 31, 451.
doi: 10.1021/om201095m pmid: 26924231 |
|
|
(d) Zhang, G.; Hanson, S. K. Org. Lett. 2013, 15, 650.
doi: 10.1021/ol303479f pmid: 26924231 |
|
|
(e) Saha, B.; Wahidur Rahaman, S. M.; Daw, P.; Sengupta, G.; Bera, J. K. Chem.-Eur. J. 2014, 20, 6542.
doi: 10.1002/chem.v20.21 pmid: 26924231 |
|
|
(f) Tamura, M.; Tomishige, K. Angew. Chem., Int. Ed. 2015, 54, 864.
doi: 10.1002/anie.201409601 pmid: 26924231 |
|
|
(g) Mukherjee, A.; Nerush, A.; Leitus, G.; Shimon, L. J. W.; Ben-David, Y.; Espinosa Jalapa, N. A.; Milstein, D. J. Am. Chem. Soc. 2016, 138, 4298.
doi: 10.1021/jacs.5b13519 pmid: 26924231 |
|
|
(h) Esteruelas, M. A.; Lezaun, V.; Martinez, A.; Olivan, M.; Onate, E. Organometallics 2017, 36, 2996.
doi: 10.1021/acs.organomet.7b00521 pmid: 26924231 |
|
| [6] |
(a) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923.
pmid: 11456996 |
|
(b) Li, Y.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2004, 126, 1794.
doi: 10.1021/ja038320g pmid: 11456996 |
|
|
(c) Ryken, S. A.; Schafer, L. L. Acc. Chem. Res. 2015, 48, 2576.
doi: 10.1021/acs.accounts.5b00224 pmid: 11456996 |
|
|
(d) Mir, R.; Dudding, T. J. Org. Chem. 2016, 81, 2675.
doi: 10.1021/acs.joc.6b00241 pmid: 11456996 |
|
| [7] |
Srimani, D.; Feller, M.; Ben-David, Y.; Milstein, D. Chem. Commun. 2012, 48, 11853.
doi: 10.1039/c2cc36639h |
| [8] |
(a) Lee, S.-H.; Nikonov, G. I. ChemCatChem 2015, 7, 107.
doi: 10.1002/cctc.v7.1 |
|
(b) Kim, D.; Kang, B.; Hong, S. H. Org. Chem. Front. 2016, 3, 475.
doi: 10.1039/C5QO00378D |
|
| [9] |
(a) Zerecero-Silva, P.; Jimenez-Solar, I.; Crestani, M. G.; Arevalo, A.; Barrios-Francisco, R.; Garcia, J. J. Appl. Catal. A 2009, 363, 230.
doi: 10.1016/j.apcata.2009.05.027 |
|
(b) Chakraborty, S.; Berke, H. ACS Catal. 2014, 4, 2191.
doi: 10.1021/cs5004646 |
|
|
(c) Choi, J.-H.; Prechtl, M. H. G. ChemCatChem 2015, 7, 1023.
doi: 10.1002/cctc.201403047 |
|
|
(d) Chakraborty, S.; Milstein, D. ACS Catal. 2017, 7, 3968.
doi: 10.1021/acscatal.7b00906 |
|
| [10] |
(a) For selected reviews, see: a Elassara, A.-Z., A.; El-Khairb, A. A. Tetrahedron 2003, 59, 8463.
doi: 10.1016/S0040-4020(03)01201-8 pmid: 15137796 |
|
(b) Stanovnik, B.; Svete, J. Chem. Rev. 2004, 104, 2433.
pmid: 15137796 |
|
|
(c) Cao, S.; Jing, Y.; Liu, Y.; Wan, J.-P. Chin. J. Org. Chem. 2014, 34, 876 (in Chinese).
doi: 10.6023/cjoc201312016 pmid: 15137796 |
|
|
(曹硕, 景艳锋, 刘云云, 万结平, 有机化学, 2014, 34, 876.)
doi: 10.6023/cjoc201312016 pmid: 15137796 |
|
|
(d) Wan, J.-P.; Gao, Y. Chem. Rec. 2016, 16, 1164.
doi: 10.1002/tcr.201500296 pmid: 15137796 |
|
|
(e) Gaber, H. M.; Bagley, M. C.; Muhammada, Z. A.; Gomha, S. M. RSC Adv. 2017, 7, 14562.
doi: 10.1039/C7RA00683G pmid: 15137796 |
|
|
(f) Fu, L.; Wan, J.-P. Asian J. Org. Chem. 2019, 8, 767.
doi: 10.1002/ajoc.v8.6 pmid: 15137796 |
|
|
(g) Wang, Z.; Zhao, B.; Liu, Y.; Wan, J.-P. Adv. Synth. Catal. 2022, 364, 1508.
doi: 10.1002/adsc.v364.9 pmid: 15137796 |
|
| [11] |
(a) Liu, X.; Cheng, R.; Zhao, F.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. Org. Lett. 2012, 14, 5480.
doi: 10.1021/ol3025583 pmid: 29419306 |
|
(b) Wang, F.; Sun, W.; Wang, Y.; Jiang, Y.; Loh, T.-P. Org. Lett. 2018, 20, 1256.
doi: 10.1021/acs.orglett.8b00222 pmid: 29419306 |
|
|
(c) Guo, Y.; Xiang, Y.; Wei, L.; Wan, J.-P. Org. Lett. 2018, 20, 3971.
doi: 10.1021/acs.orglett.8b01536 pmid: 29419306 |
|
| [12] |
(a) Sun, J.; Zhang-Negrerie, D.; Du, Y. Adv. Synth. Catal. 2016, 358, 2035.
doi: 10.1002/adsc.v358.13 pmid: 31457578 |
|
(b) Rafique, J.; Saba, S.; Schneider, A. R.; Franco, M. S.; Silva, S. M.; Braga, A. L. ACS Omega 2017, 2, 2280.
doi: 10.1021/acsomega.7b00445 pmid: 31457578 |
|
|
(c) Shang, Z.; Chen, Q.; Xing, L.; Zhang, Y.; Wait, L.; Du, Y. Adv. Synth. Catal. 2019, 361, 4926.
doi: 10.1002/adsc.v361.21 pmid: 31457578 |
|
| [13] |
(a) C—H Arylation: Ge, H.; Niphakis, M. J.; Georg, G. I. J. Am. Chem. Soc. 2008, 130, 3708.
doi: 10.1021/ja710221c |
|
(b) Wurtz, S.; Rakshit, S.; Neumann, J. J.; Droge, T.; Glorius, F. Angew. Chem., Int. Ed. 2008, 47, 7230.
doi: 10.1002/anie.v47:38 |
|
|
(c) Yu, W.; Du, Y.; Zhao, K. Org. Lett. 2009, 11, 2417.
doi: 10.1021/ol900576a |
|
|
(d) Yu, Y.-Y.; Bi, L. Georg, G. I. J. Org. Chem. 2013, 78, 6163.
doi: 10.1021/jo400830t |
|
|
(e) Wan, J.-P.; Tu, Z.; Wang, Y. Chem.-Eur. J. 2019, 25, 6907.
doi: 10.1002/chem.v25.28 |
|
|
(f) Mkrtchyan, S.; Laroshenko, V. O. Chem. Commun. 2020, 56, 2606.
doi: 10.1039/C9CC09945J |
|
| [14] |
(a) Yu, Y.; Niphakis, M. J.; Georg, G. I. Org. Lett. 2011, 13, 5932.
doi: 10.1021/ol202677g |
|
(b) Fu, L.; Xu, Z.; Wan, J.-P.; Liu, Y. Org. Lett. 2020, 22, 9518.
doi: 10.1021/acs.orglett.0c03548 |
|
|
(c) Fu, L.; Liu, Y.; Wan, J.-P. Org. Lett. 2021, 23, 4363.
doi: 10.1021/acs.orglett.1c01301 |
|
| [15] |
(a) Jiang, Y.; Liang, G.; Zhang, C.; Loh, T.-P. Eur. J. Org. Chem. 2016, 2016, 3326.
doi: 10.1002/ejoc.v2016.20 |
|
(b) Wan, J.-P.; Zhong, S.; Xie, L.; Cao, X.; Liu, Y.; Wei, L. Org. Lett. 2016, 18, 584.
doi: 10.1021/acs.orglett.5b03608 |
|
|
(c) Gao, Y.; Hu, C.; Wen, C.; Wan, J.-P. ACS Omega 2017, 2, 7784.
doi: 10.1021/acsomega.7b01422 |
|
|
(d) Gao, Y.; Liu, Y.; Wan, J.-P. J. Org. Chem. 2019, 84, 2243.
doi: 10.1021/acs.joc.8b02981 |
|
| [16] |
(a) Wan, J.-P.; Zhong, S.; Guo, Y.; Wei, L. Eur. J. Org. Chem. 2017, 2017, 4401.
doi: 10.1002/ejoc.v2017.30 |
|
(b) Tian, L.; Wan, J.-P.; Sheng, S. ChemCatChem 2020, 12, 2533.
doi: 10.1002/cctc.v12.9 |
|
|
(c) Yu, Q.; Liu, Y.; Wan, J.-P. Chin. Chem. Lett. 2021, 32, 3514.
doi: 10.1016/j.cclet.2021.04.037 |
|
| [17] |
(a) Jiang, H.; Huang, W.; Yu, Y.; Yi, S.; Li, J.; Wu, W. Chem. Commun. 2017, 53, 7473.
doi: 10.1039/C7CC03125D |
|
(b) Xiang, H.; Zhao, Q.; Tang, Z.; Xiao, J.; Xia, P.; Wang, C.; Yang, C.; Chen, X.; Yang, H. Org. Lett. 2017, 19, 146.
doi: 10.1021/acs.orglett.6b03441 |
|
|
(c) Sun, J.; Zhen, X.; Ge, H.; Zhang, G. An, X.; Du, Y. Beilstein J. Org. Chem. 2018, 14, 1452.
doi: 10.3762/bjoc.14.123 |
|
|
(d) Yu, Q.; Liu, Y.; Wan, J.-P. Org. Chem. Front. 2020, 7, 2770.
doi: 10.1039/D0QO00855A |
|
| [18] |
Zhang, Y.; Zhao, X.; Zhuang, C.; Wang, S.; Zhang-Negrerie, D.; Du, Y. Adv. Synth. Catal. 2018, 360, 2107.
doi: 10.1002/adsc.v360.11 |
| [19] |
(a) Yuan, J.; Zhang, Q.; Yu, M.; Huang, P.; Zhang, R.; Dong, D. Org. Lett. 2015, 17, 5012.
doi: 10.1021/acs.orglett.5b02485 pmid: 25658698 |
|
(b) Sun, X.; Lyu, Y.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. Org. Lett. 2013, 15, 6222.
doi: 10.1021/ol4030716 pmid: 25658698 |
|
|
(c) Luo, T.; Wan, J.-P.; Liu, Y. Org. Chem. Front. 2020, 7, 1107.
doi: 10.1039/D0QO00065E pmid: 25658698 |
|
|
(d) Yuan, Y.; Hou, W.; Zhang-Negrerie, D.; Zhao, K.; Du, Y. Org. Lett. 2014, 16, 5410.
doi: 10.1021/ol5026525 pmid: 25658698 |
|
|
(e) Zheng, C.; Wang, Y.; Fan, R. Org. Lett. 2015, 17, 916.
doi: 10.1021/acs.orglett.5b00026 pmid: 25658698 |
|
|
(f) Duan, X.; Li, H.; Li, W.; Wang, J.; Liu, N. ChemistrySelect 2021, 6, 6478.
doi: 10.1002/slct.v6.25 pmid: 25658698 |
|
| [20] |
(a) Zhang, H.; Xu, J.; Ouyang, Y.; Yue, X.; Zhou, C.; Ni, Z.; Li, W. Chin. Chem. Lett. 2022, 33, 2036.
doi: 10.1016/j.cclet.2021.09.069 pmid: 26027938 |
|
(b) Gonzalez-de-Castro, A.; Xiao, J. J. Am. Chem. Soc. 2015, 137, 8206.
doi: 10.1021/jacs.5b03956 pmid: 26027938 |
|
|
(c) Cheng, Z.; Jin, W.; Liu, C. Org. Chem. Front. 2019, 6, 841.
doi: 10.1039/c8qo01412d pmid: 26027938 |
|
|
(d) Xu, J.; Yue, X.; He, L.; Shen, J.; Ouyang, Y.; Liang, C.; Li, W. ACS Sustainable Chem. Eng. 2022, 10, 14119.
doi: 10.1021/acssuschemeng.1c06755 pmid: 26027938 |
|
|
(e) Liu, K.-J.; Deng, J.-H.; Zeng, T.-Y.; Chen, X.-J.; Huang, Y.; Cao, Z.; Lin, Y.-W.; He, W.-M. Chin. Chem. Lett. 2020, 31, 1868.
doi: 10.1016/j.cclet.2020.01.036 pmid: 26027938 |
|
|
(f) Xu, J.; He, L.; Liang, C.; Yue, X.; Ouyang, Y.; Zhang, P. ACS Sustainable Chem. Eng. 2021, 9, 13663.
doi: 10.1021/acssuschemeng.1c05237 pmid: 26027938 |
|
|
(g) Zhang, Y.; Hatami, N.; Lange, N. S.; Ronge, E.; Schilling, W.; Jooss, C.; Das, S. Green Chem. 2020, 22, 4516.
doi: 10.1039/D0GC01187H pmid: 26027938 |
|
|
(h) Xu, J.; Huang, L.; He, L.; Liang, C.; Ouyang, Y.; Shen, J.; Jiang, M.; Li, W. Green Chem. 2021, 23, 6632.
doi: 10.1039/D1GC01899J pmid: 26027938 |
|
|
(i) Huang, L.; Xu, J.; He, L.; Liang, C.; Ouyang, Y.; Yu, Y.; Li, W.; Zhang, P. Chin. Chem. Lett. 2021, 32, 3627.
doi: 10.1016/j.cclet.2021.04.016 pmid: 26027938 |
|
|
(j) Li, W.; Li, S.; Luo, L.; Ge, Y.; Xu, J.; Zheng, X.; Yuan, M.; Li, R.; Chen, H.; Fu, H. Green Chem. 2021, 23, 3649.
doi: 10.1039/D1GC00716E pmid: 26027938 |
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