Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (10): 4007-4013.DOI: 10.6023/cjoc202105050 Previous Articles Next Articles
Special Issue: 南开大学化学学科创立100周年; 热点论文虚拟合集
ARTICLES
收稿日期:
2021-05-29
修回日期:
2021-07-31
发布日期:
2021-08-17
通讯作者:
贾义霞
基金资助:
Jun Lu, Renxiao Liang, Yixia Jia()
Received:
2021-05-29
Revised:
2021-07-31
Published:
2021-08-17
Contact:
Yixia Jia
Supported by:
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Jun Lu, Renxiao Liang, Yixia Jia. Copper-Catalyzed Intramolecular Dearomative Arylation of Naphthylamines[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4007-4013.
Entry | Solvent | Base | Ligand | Yieldb/% |
---|---|---|---|---|
1 | THF | tBuOLi | 1,10-Phen | 20 |
2 | Dioxane | tBuOLi | 1,10-Phen | 50 |
3 | Toluene | tBuOLi | 1,10-Phen | 23 |
4 | DMSO | tBuOLi | 1,10-Phen | 92 |
5 | DMSO | Et3N | 1,10-Phen | NR |
6 | DMSO | K3PO4 | 1,10-Phen | 85 |
7 | DMSO | K2CO3 | 1,10-Phen | 89 |
8 | DMSO | tBuOLi | IMes | 27 |
9 | DMSO | tBuOLi | L-Proline | 29 |
10 | DMSO | tBuOLi | — | 25 |
11c | DMSO | tBuOLi | 1,10-Phen | 66 |
12d | DMSO | tBuOLi | 1,10-Phen | 72 |
13e | DMSO | tBuOLi | 1,10-Phen | NR |
Entry | Solvent | Base | Ligand | Yieldb/% |
---|---|---|---|---|
1 | THF | tBuOLi | 1,10-Phen | 20 |
2 | Dioxane | tBuOLi | 1,10-Phen | 50 |
3 | Toluene | tBuOLi | 1,10-Phen | 23 |
4 | DMSO | tBuOLi | 1,10-Phen | 92 |
5 | DMSO | Et3N | 1,10-Phen | NR |
6 | DMSO | K3PO4 | 1,10-Phen | 85 |
7 | DMSO | K2CO3 | 1,10-Phen | 89 |
8 | DMSO | tBuOLi | IMes | 27 |
9 | DMSO | tBuOLi | L-Proline | 29 |
10 | DMSO | tBuOLi | — | 25 |
11c | DMSO | tBuOLi | 1,10-Phen | 66 |
12d | DMSO | tBuOLi | 1,10-Phen | 72 |
13e | DMSO | tBuOLi | 1,10-Phen | NR |
[1] |
(a) Zheng, C.; You, S.-L. ACS Cent. Sci. 2021, 7, 432.
doi: 10.1021/acscentsci.0c01651 |
(b) Sharma, U. K.; Ranjan, P.; Van der Eycken, E. V.; You, S.-L. Chem. Soc. Rev. 2020, 49, 8721.
doi: 10.1039/D0CS00128G |
|
(c) Huang, G.; Yin, B. Adv. Synth. Catal. 2019, 361, 405.
doi: 10.1002/adsc.v361.3 |
|
(d) Wu, W.-T.; Zhang, L.; You, S.-L. Chem. Soc. Rev. 2016, 45, 1570.
doi: 10.1039/C5CS00356C |
|
(e) Zheng, C.; You, S.-L. Chem 2016, 1, 830.
doi: 10.1016/j.chempr.2016.11.005 |
|
(f) Zhuo, C.-X.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2014, 47, 2558.
doi: 10.1021/ar500167f |
|
(g) Zhuo, C.-X.; Zhang, W.; You, S.-L. Angew. Chem., Int. Ed. 2012, 51, 1266.
|
|
(h) Li, K.; Bai, L.; Luan, X. Chin. J. Org. Chem. 2019, 39, 2211. (in Chinese)
doi: 10.6023/cjoc201903065 |
|
(李锟雨, 白璐, 栾新军, 2019, 39, 2211.)
|
|
(i) Yan, Q.; Fan, R.; Liu, B.; Su, S.; Wang, B.; Yao, T.; Tan, J. Chin. J. Org. Chem. 2021, 41, 455. (in Chinese)
doi: 10.6023/cjoc202009009 |
|
(闫强, 范荣, 刘斌斌, 苏帅松, 王勃, 姚团利, 谭嘉靖, 有机化学, 2021, 41, 455.)
doi: 10.6023/cjoc202009009 |
|
[2] |
(a) Bai, Y.; Liu, A.; Wu, X.-X.; Chen, S.; Wang, J. J. Org. Chem. 2020, 85, 6687.
doi: 10.1021/acs.joc.0c00710 pmid: 21612204 |
(b) Hu, J.; Pan, S.; Zhu, S.; Yu, P.; Xu, R; Zhong, G.; Zeng, X. J. Org. Chem. 2020, 85, 7896.
doi: 10.1021/acs.joc.0c00582 pmid: 21612204 |
|
(c) Wu, X.-X.; Liu, A.; Mou, M.; Chen, H.; Chen, S. J. Org. Chem. 2018, 83, 14181.
doi: 10.1021/acs.joc.8b02363 pmid: 21612204 |
|
(d) Fan, L.; Liu, J.; Bai, L.; Wang, Y.; Luan, X. Angew. Chem., Int. Ed. 2017, 56, 14257.
doi: 10.1002/anie.201708310 pmid: 21612204 |
|
(e) Luo, L.; Zheng, H.; Liu, J.; Wang, H.; Wang, Y.; Luan, X. Org. Lett. 2016, 18, 2082.
doi: 10.1021/acs.orglett.6b00710 pmid: 21612204 |
|
(f) Nemoto, T., Nozaki, T.; Yoshida, M.; Hamada, Y. Adv. Synth. Catal. 2013, 355, 2693.
doi: 10.1002/adsc.201300326 pmid: 21612204 |
|
(g) Nemoto, T.; Zhao, Z. D.; Yokosaka, T.; Suzuki, Y.; Wu, R.; Hamada, Y. Angew. Chem., Int. Ed. 2013, 52, 2217.
doi: 10.1002/anie.201209317 pmid: 21612204 |
|
(h) Yoshida, M.; Nemoto, T.; Zhao, Z.; Ishige, Y.; Hamada, Y. Tetrahedron: Asymmetry 2012, 23, 859.
doi: 10.1016/j.tetasy.2012.05.026 pmid: 21612204 |
|
(i) Rousseaux, S.; Fortanet, J. G.; Sanchez, M. A. D. A.; Buchwald, S. L. J. Am. Chem. Soc. 2011, 133, 9282.
doi: 10.1021/ja203644q pmid: 21612204 |
|
(j) Wu, Q.-F.; Liu, W.-B.; Zhuo, C.-X.; Rong, Z.-Q.; Ye, K.-Y.; You, S.-L. Angew. Chem., Int. Ed. 2011, 50, 4455.
doi: 10.1002/anie.201100206 pmid: 21612204 |
|
(k) Nemoto, T.; Ishige, Y.; Yoshida, M.; Kohno, Y.; Kanematsu, M.; Hamada, Y. Org. Lett. 2010, 12, 5020.
doi: 10.1021/ol102190s pmid: 21612204 |
|
[3] |
(a) Bedford, R. B.; Fey, N.; Haddow, M. F.; Sankey, R. F. Chem. Commun. 2011, 47, 3649.
doi: 10.1039/c0cc05033d |
(b) Bedford, R. B.; Butts, C. P.; Haddow, M. F.; Osborne, R.; Sankey, R. F. Chem. Commun. 2009, 4832.
|
|
[4] |
(a) Fu, Z.; Zhu, J.; Guo, S.; Lin, A. Chem. Commun. 2021, 57, 1262.
doi: 10.1039/D0CC07529A pmid: 23427905 |
(b) Yamaguchi, M.; Fujiwara, S.; Manabe, K. Org. Lett. 2019, 21, 6972.
doi: 10.1021/acs.orglett.9b02559 pmid: 23427905 |
|
(c) Ding, L.; Gao, R.-D.; You, S. L. Chem. Eur. J. 2019, 25, 4330.
doi: 10.1002/chem.v25.17 pmid: 23427905 |
|
(d) Fang, X.; Li, Q.; Shi, R.; Yao, H.; Lin, A. Org. Lett. 2018, 20, 6084.
doi: 10.1021/acs.orglett.8b02481 pmid: 23427905 |
|
(e) Trost, B. M.; Bai, W.-J.; Hohn, C.; Bai, Y.; Cregg, J. J. Am. Chem. Soc. 2018, 140, 6710.
doi: 10.1021/jacs.8b03656 pmid: 23427905 |
|
(f) Gao, R.-D.; Ding, L.; Zheng, C.; Dai, L.-X.; You, S.-L. Org. Lett. 2018, 20, 748.
doi: 10.1021/acs.orglett.7b03887 pmid: 23427905 |
|
(g) Gao, S.; Wu, Z.; Fang, X.; Lin, A.; Yao, H. Org. Lett. 2016, 18, 3906.
doi: 10.1021/acs.orglett.6b01947 pmid: 23427905 |
|
(h) Gao, R.-D.; Xu, Q.-L.; Zhang, B.; Gu, Y.; Dai, L.-X.; You, S.-L. Chem. Eur. J. 2016, 22, 11601.
doi: 10.1002/chem.201602691 pmid: 23427905 |
|
(i) Zhang, H.; Hu, R.-B.; Liu, N.; Li, S.-X.; Yang, S.-D. Org. Lett. 2016, 18, 28.
doi: 10.1021/acs.orglett.5b03053 pmid: 23427905 |
|
(j) Zhuo, C.-X.; Cheng, Q.; Liu, W.-B.; Zhao, Q.; You, S.-L. Angew. Chem., Int. Ed. 2015, 54, 8475.
doi: 10.1002/anie.201502259 pmid: 23427905 |
|
(k) Gao, R.-D.; Liu, C.; Dai, L.-X.; Zhang, W.; You, S.-L. Org. Lett. 2014, 16, 3919.
doi: 10.1021/ol501704q pmid: 23427905 |
|
(l) Yang, Z.-P.; Zhuo, C.-X.; You, S.-L. Adv. Synth. Catal. 2014, 356, 1731.
doi: 10.1002/adsc.201301083 pmid: 23427905 |
|
(m) Zhang, X.; Han, L.; You, S.-L. Chem. Sci. 2014, 5, 1059.
doi: 10.1039/c3sc53019a pmid: 23427905 |
|
(n) Zhang, X.; Liu, W.-B.; Wu, Q.-F.; You, S.-L. Org. Lett. 2013, 15, 3746.
doi: 10.1021/ol4016578 pmid: 23427905 |
|
(o) Montgomery, T. D.; Zhu, Y.; Kagawa, N.; Rawal, V. H. Org. Lett. 2013, 15, 1140.
doi: 10.1021/ol400334u pmid: 23427905 |
|
(p) Wu, K.-J.; Dai, L.-X.; You, S.-L. Org. Lett. 2012, 14, 3772.
doi: 10.1021/ol301663h pmid: 23427905 |
|
(q) Wu, Q.-F.; Zheng, C.; You, S.-L. Angew. Chem., Int. Ed. 2012, 51, 1680.
doi: 10.1002/anie.v51.7 pmid: 23427905 |
|
(r) Wu, K.-J.; Dai, L.-X.; You, S.-L. Org. Lett. 2012, 14, 3772.
doi: 10.1021/ol301663h pmid: 23427905 |
|
(s) Trost, B. M.; Quancard, J. J. Am. Chem. Soc. 2006, 128, 6314.
doi: 10.1021/ja0608139 pmid: 23427905 |
|
(t) Kimura, M.; Futamata, M.; Mukai, R.; Tamaru, Y. J. Am. Chem. Soc. 2005, 127, 4592.
doi: 10.1021/ja0501161 pmid: 23427905 |
|
[5] |
(a) Liang, R.-X.; Song, L.-J.; Lu, J.-B.; Xu, W.-Y.; Ding, C.; Jia, Y.-X. Angew. Chem., Int. Ed. 2021, 60, 7412.
doi: 10.1002/anie.v60.13 pmid: 32873772 |
(b) Zhou, B.; Wang, H.; Cao, Z.-Y.; Zhu, J.-W.; Liang, R.-X.; Jia, Y.-X. Nat. Commun. 2020, 11, 4380.
doi: 10.1038/s41467-020-18137-w pmid: 32873772 |
|
(c) Liang, R.-X.; Wang, K.; Wu, Q.; Sheng, W.-J.; Jia, Y.-X. Organometallics 2019, 38, 3927.
doi: 10.1021/acs.organomet.9b00112 pmid: 32873772 |
|
(d) Weng, J.-Q.; Xing, L.-L.; Hou, W.-R.; Liang, R.-X.; Jia, Y.-X. Org. Chem. Front. 2019, 6, 1577.
doi: 10.1039/C9QO00246D pmid: 32873772 |
|
(e) Marchese, A. D.; Lind, F.; MahonÁ, E.; Yoon, H.; Lautens, M. Angew. Chem., Int. Ed. 2019, 58, 5095.
doi: 10.1002/anie.v58.15 pmid: 32873772 |
|
(f) Liang, R.-X.; Wang, K.; Song, L.-J.; Sheng, W.-J.; Jia, Y.-X. RSC Adv. 2019, 9, 13959.
doi: 10.1039/C9RA02569C pmid: 32873772 |
|
(g) Shen, C.; Zeidan, N.; Wu, Q.; Breuers, C. B. J.; Liu, R.-R.; Jia, Y.-X.; Lautens, M. Chem. Sci. 2019, 10, 3118.
doi: 10.1039/C8SC05737K pmid: 32873772 |
|
(h) Li, X.; Zhou, B.; Yang, R.-Z.; Yang, F.-M.; Liang, R.-X.; Liu, R.-R.; Jia, Y.-X. J. Am. Chem. Soc. 2018, 140, 13945.
doi: 10.1021/jacs.8b09186 pmid: 32873772 |
|
(i) Zeidan, N.; Beisel, T.; Ross, R.; Lautens, M. Org. Lett. 2018, 20, 7332.
doi: 10.1021/acs.orglett.8b03310 pmid: 32873772 |
|
(j) Yang, P.; You, S.-L. Org. Lett. 2018, 20, 7684.
doi: 10.1021/acs.orglett.8b03425 pmid: 32873772 |
|
[6] |
(a) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450.
doi: 10.1021/ar8000298 |
(b) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
doi: 10.1021/cr000664r |
|
[7] |
(a) Gao, D.; Parvez, M.; Back, T. G. Chem. Eur. J. 2010, 16, 14281.
doi: 10.1002/chem.201002628 |
(b) Bernini, R.; Cacchi, S.; Fabrizi, G.; Filisti, E.; Sferrazza, A. Synlett 2009, 1480.
|
|
(c) Yan, S.; Wu, H.; Wu, N.; Jiang, Y. Synlett 2007, 2699.
|
|
(d) Osuka, A.; Mori, Y.; Suzuki, H. Chem. Lett. 1982, 12, 2031.
|
|
[8] |
Fortanet, J. G.; Kessler, F.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 6676.
doi: 10.1021/ja9025193 |
[9] |
(a) Liang, R.-X.; Zhong, C.; Liu, Z.-H.; Yang, M.; Tang, H.-W.; Chen, J.-F.; Yang, Y.-F.; Jia, Y.-X. ACS Catal. 2021, 11, 1827.
doi: 10.1021/acscatal.0c05020 |
(b) Xu, H.-B.; Zhu, Y.-Y.; Dong, L. J. Org. Chem. 2019, 84, 16286.
doi: 10.1021/acs.joc.9b02468 |
|
(c) Jana, N.; Zhou, F.; Driver, T. G. J. Am. Chem. Soc. 2015, 137, 6738.
doi: 10.1021/jacs.5b02946 |
|
(d) Kong, C.; Driver, T. G. Org. Lett. 2015, 17, 802.
doi: 10.1021/ol503541z |
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