有机化学 ›› 2019, Vol. 39 ›› Issue (11): 3154-3161.DOI: 10.6023/cjoc201904062 上一篇 下一篇
所属专题: 碳氢活化合辑2018-2019
研究论文
收稿日期:
2019-04-25
发布日期:
2019-06-19
Xing Lihao, Shao Lingyan*(), Fu Xiaopan, Deng Kezuan, Yang Jinyue, Ji Yafei*()
Received:
2019-04-25
Published:
2019-06-19
Contact:
Shao Lingyan,Ji Yafei
E-mail:shaoly520@163.com;jyf@ecust.edu.cn
Supported by:
文章分享
发展了一种钯催化,4-芳基噻唑化合物邻位C(sp2)-H键碘化的反应体系.通过定位基筛选以及反应条件优化得到最高效的单选择性邻位碘化反应条件,并应用于一系列含不同取代基的4-(2-碘代芳基)噻唑的合成中.该催化体系呈现出良好的底物适应性.通过简单的后续衍生化即可将碘化产物转化为多种基团取代产物,为该方法学研究提供了更高的应用价值.通过氘代动力学研究以及自由基抑制实验,提出了合理的催化循环机理.
. 钯催化噻唑定位基导向的单选择性C(sp2)-H键碘化反应[J]. 有机化学, 2019, 39(11): 3154-3161.
Xing Lihao, Shao Lingyan, Fu Xiaopan, Deng Kezuan, Yang Jinyue, Ji Yafei. Palladium-Catalyzed Thiazole-Directed mono-Selective C(sp2)-H Bond Iodination Reaction[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3154-3161.
Entry | Catalyst | NIS (equiv.) | Solvent | Yieldb/% | |
1 | None | 2.0 | DCE/HFIP | (V:V=4:1) | 0 |
2 | Pd(OAc)2 | 2.0 | DCE/HFIP | (V:V=4:1) | 76 |
3 | Pd(CH3CN)2Cl2 | 2.0 | DCE/HFIP | (V:V=4:1) | 64 |
4 | Pd(TFA)2 | 2.0 | DCE/HFIP | (V:V=4:1) | 57 |
5 | PdCl2 | 2.0 | DCE/HFIP | (V:V=4:1) | 38 |
6 | Pd(PPh3)2Cl2 | 2.0 | DCE/HFIP | (V:V=4:1) | 27 |
7c | Pd(OAc)2 | 2.0 | DCE/HFIP | (V:V=4:1) | 58 |
8d | Pd(OAc)2 | 2.0 | DCE/HFIP | (V:V=4:1) | 75 |
9 | Pd(OAc)2 | 2.0 | DCE | 86 | |
10 | Pd(OAc)2 | 2.0 | HFIP | 69 | |
11 | Pd(OAc)2 | 2.0 | DMF | 85 | |
12 | Pd(OAc)2 | 2.0 | DCM | 62 | |
13 | Pd(OAc)2 | 2.0 | TCM | 21 | |
14 | Pd(OAc)2 | 1.5 | DCE | 76 | |
15 | Pd(OAc)2 | 2.5 | DCE | 93 | |
16 | Pd(OAc)2 | 3.0 | DCE | 92 | |
17e | Pd(OAc)2 | 2.5 | DCE | 78 | |
18f | Pd(OAc)2 | 2.5 | DCE | 90 |
Entry | Catalyst | NIS (equiv.) | Solvent | Yieldb/% | |
1 | None | 2.0 | DCE/HFIP | (V:V=4:1) | 0 |
2 | Pd(OAc)2 | 2.0 | DCE/HFIP | (V:V=4:1) | 76 |
3 | Pd(CH3CN)2Cl2 | 2.0 | DCE/HFIP | (V:V=4:1) | 64 |
4 | Pd(TFA)2 | 2.0 | DCE/HFIP | (V:V=4:1) | 57 |
5 | PdCl2 | 2.0 | DCE/HFIP | (V:V=4:1) | 38 |
6 | Pd(PPh3)2Cl2 | 2.0 | DCE/HFIP | (V:V=4:1) | 27 |
7c | Pd(OAc)2 | 2.0 | DCE/HFIP | (V:V=4:1) | 58 |
8d | Pd(OAc)2 | 2.0 | DCE/HFIP | (V:V=4:1) | 75 |
9 | Pd(OAc)2 | 2.0 | DCE | 86 | |
10 | Pd(OAc)2 | 2.0 | HFIP | 69 | |
11 | Pd(OAc)2 | 2.0 | DMF | 85 | |
12 | Pd(OAc)2 | 2.0 | DCM | 62 | |
13 | Pd(OAc)2 | 2.0 | TCM | 21 | |
14 | Pd(OAc)2 | 1.5 | DCE | 76 | |
15 | Pd(OAc)2 | 2.5 | DCE | 93 | |
16 | Pd(OAc)2 | 3.0 | DCE | 92 | |
17e | Pd(OAc)2 | 2.5 | DCE | 78 | |
18f | Pd(OAc)2 | 2.5 | DCE | 90 |
[1] |
Gribble G. W. Acc. Chem. Res. 1998 31 141.
doi: 10.1021/ar9701777 |
[2] |
Lindley J. Tetrahedron 1984 40 1433.
doi: 10.1016/S0040-4020(01)91791-0 |
[3] |
Suzuki A. J. Organomet. Chem. 1999 576 147.
doi: 10.1016/S0022-328X(98)01055-9 |
[4] |
Crisp T. G. Chem. Soc. Rev. 1998 27 427.
doi: 10.1039/a827427z |
[5] |
Sambiagio C. Marsden S. P. Blacker A. J. McGowan P. C. Chem. Soc. Rev. 2014 43 3525.
doi: 10.1039/C3CS60289C |
[6] | Merkushev E. B. Synthesis 1988 923 |
[7] |
(a) Li, B.; Liu, B.; Shi, B. F. Chem. Commun. 2015, 51, 5093.
doi: 10.1039/C5CC00531K |
(b) Pal, P.; Singh, H.; Panda, A. B.; Ghosh, S. C. Asian J. Org. Chem. 2015, 4, 879.
doi: 10.1039/C5CC00531K |
|
(c) Zhan, B. B.; Liu, Y. H.; Hu, F.; Shi, B. F. Chem. Commun. 2016, 52, 4934.
doi: 10.1039/C5CC00531K |
|
(d) Aihara, Y.; Chatani, N. ACS Catal. 2016, 6, 4323.
doi: 10.1039/C5CC00531K |
|
(e) Khan, B.; Kant, R.; Koley, D. Adv. Synth. Catal. 2016, 358, 2352.
doi: 10.1039/C5CC00531K |
|
(f) Kommagalla, Y.; Yamazaki, K.; Yamaguchi, T.; Chatani, N. Chem. Commun. 2018, 54, 1359.
doi: 10.1039/C5CC00531K |
|
(g) Singh, H.; Sen, C.; Sahoo, T.; Ghosh, S. C. Eur. J. Org. Chem. 2018, 34, 4748.
doi: 10.1039/C5CC00531K |
|
(h) Du, Y.; Liu, Y. Y.; Wan, J. P. J. Org. Chem. 2018, 83, 3403.
doi: 10.1039/C5CC00531K |
|
[8] |
Kalyani D. Dick A. R. Anani W. Q. Sanford M. S. Org. Lett. 2006 8 2523.
doi: 10.1021/ol060747f |
[9] |
(a) Giri, R.; Chen, X.; Yu, J. Q. Angew. Chem., Int. Ed. 2005, 44, 2112.
doi: 10.1002/(ISSN)1521-3773 |
(b) Li, J. J.; Mei, T. S.; Yu, J. Q. Angew. Chem., Int. Ed. 2008, 47, 6452.
doi: 10.1002/(ISSN)1521-3773 |
|
(c) Mei, T. S.; Giri, R.; Maugel, N.; Yu, J. Q. Angew. Chem., Int. Ed. 2008, 47, 5215.
doi: 10.1002/(ISSN)1521-3773 |
|
(d) Mei, T. S.; Wang, D. H.; Yu, J. Q. Org. Lett. 2010, 12, 3140.
doi: 10.1002/(ISSN)1521-3773 |
|
(e) Nack, W. A.; Wang, X.; Wang, B.; He, G.; Chen, G. Beilstein J. Org. Chem. 2016, 12, 1243.
doi: 10.1002/(ISSN)1521-3773 |
|
(f) Zhu, R. Y.; Liu, L. Y.; Yu, J. Q. J. Am. Chem. Soc. 2017, 139, 12394.
doi: 10.1002/(ISSN)1521-3773 |
|
(g) Zhu, R. Y.; Saint-Denis, T. G.; Shao, Y.; He, J.; Sieber, J. D.; Senanayake, C. H.; Yu, J. Q. J. Am. Chem. Soc. 2017, 139, 5724.
doi: 10.1002/(ISSN)1521-3773 |
|
[10] |
(a) Dudnik, A. S.; Chernyak, N.; Huang, C.; Gevorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 8729.
doi: 10.1002/anie.201004426 |
(b) Du, B.; Jiang, X.; Sun, P. J. Org. Chem. 2013, 78, 2786.
doi: 10.1002/anie.201004426 |
|
(c) Sadhu, P.; Alla, S. K.; Punniyamurthy, T. J. Org. Chem. 2013, 78, 6104.
doi: 10.1002/anie.201004426 |
|
(d) Pascanu, V.; Carson, F.; Solano, M. V.; Su, J.; Zou, X.; Johansson, M. J.; Martin-Matute, B. Chem. -Eur. J. 2016, 22, 3729.
doi: 10.1002/anie.201004426 |
|
(e) Testa, C.; Gigot, E.; Genc, S.; Decreau, R.; Roger, J.; Hierso, J. C. Angew. Chem., Int. Ed. 2016, 55, 5555.
doi: 10.1002/anie.201004426 |
|
(f) Yang, X.; Sun, Y.; Sun, T. Y.; Rao, Y. Chem. Commun. 2016, 52, 6423.
doi: 10.1002/anie.201004426 |
|
(g) Das, R.; Kapur, M. J. Org. Chem. 2017, 82, 1114.
doi: 10.1002/anie.201004426 |
|
(h) Dubost, E.; Babin, V.; Benoist, F.; Hebert, A.; Barbey, P.; Chollet, C.; Bouillon, J. P.; Manrique, A.; Pieters, G.; Fabis, F.; Cailly, T. Org. Lett. 2018, 20, 6302.
doi: 10.1002/anie.201004426 |
|
(i) Tang, R. J.; Milcent, T.; Crousse, B. J. Org. Chem. 2018, 83, 930.
doi: 10.1002/anie.201004426 |
|
[11] |
(a) Chu, L.; Wang, X. C.; Moore, C. E.; Rheingold, A. L.; Yu, J. Q. J. Am. Chem. Soc. 2013, 135, 16344.
doi: 10.1021/ja408864c |
(b) Wang, X. C.; Hu, Y.; Bonacorsi, S.; Hong, Y.; Burrell, R.; Yu, J. Q. J. Am. Chem. Soc. 2013, 135, 10326.
doi: 10.1021/ja408864c |
|
(c) Chu, L.; Xiao, K. J.; Yu, J. Q. Science 2014, 346, 451
doi: 10.1021/ja408864c |
|
[12] |
(a) Lu, C.; Zhang, S. Y.; He, G.; Nack, W. A.; Chen, G. Tetrahedron 2014, 70, 4197.
doi: 10.1016/j.tet.2014.02.070 |
(b) Chu, L.; Shang, M.; Tanaka, K.; Chen, Q.; Pissarnitski, N.; Streckfuss, E.; Yu, J. Q. ACS Cent. Sci. 2015, 1, 394.
doi: 10.1016/j.tet.2014.02.070 |
|
(c) Sun, X.; Yao, X.; Zhang, C.; Rao, Y. Chem. Commun. 2015, 51, 10014.
doi: 10.1016/j.tet.2014.02.070 |
|
(d) Fan, X. M.; Guo, Y.; Li, Y. D.; Yu, K. K.; Liu, H. W.; Liao, D. H.; Ji, Y. F. Asian J. Org. Chem. 2016, 5, 499.
doi: 10.1016/j.tet.2014.02.070 |
|
[13] |
(a) Das, R.; Kapur, M. Asian J. Org. Chem. 2018, 7, 1524.
doi: 10.1002/ajoc.201800142 |
(b) Liao, G.; Shi, B. F. Acta Chim. Sinica. 2015, 73, 1283 (in Chinese).
doi: 10.1002/ajoc.201800142 |
|
(廖港, 史炳烽, 化学学报, 2015, 73, 1283.)
doi: 10.1002/ajoc.201800142 |
|
[14] |
Santra S. K. Banerjee A. Khatun N. Samanta A. Patel B. K. RSC Adv. 2015 5 11960.
doi: 10.1039/C4RA15461D |
[15] |
(a) Al-Ghorbani, M.; Alghamdi, H. A.; Khanum, S. A. Eur. J. Biomed. Pharm. Sci. 2018, 5, 1.
doi: 10.3390/molecules23030685 |
(b) Attri, C.; Bhatia, P.; Kumar, P. J. Mod. Chem. Chem. Technol. 2018, 9, 19.
doi: 10.3390/molecules23030685 |
|
(c) Liaras, K.; Fesatidou, M.; Geronikaki, A. Molecules 2018, 23, 685/1.
doi: 10.3390/molecules23030685 |
|
(d) de Siqueira, L. R. P.; de Moraes Gomes, P. A. T.; de Lima Ferreira, L. P.; de Melo Rego, M. J. B.; Leite, A. C. L. Eur. J. Med. Chem. 2019, 170, 237.
doi: 10.3390/molecules23030685 |
|
(e) Scarim, C. B.; Jornada, D. H.; Machado, M. G. M.; Ferreira, C. M. R.; dos Santos, J. L.; Chung, M. C. Eur. J. Med. Chem. 2019, 162, 378.
doi: 10.3390/molecules23030685 |
|
[16] |
Yu K. K. Guo Y. Hu Y. H. Xu Z. Liu H. W. Liao D. H. Ji Y. F. Asian J. Org. Chem. 2016 5 1219.
doi: 10.1002/ajoc.201600304 |
[17] |
Bergstr m M. Suresh G. Naidu V. R. Unelius C. R. Eur. J. Org. Chem. 2017 2017 3234.
doi: 10.1002/ejoc.201700173 |
[18] |
Qiao H. J. Yang F. Wang S. W. Leng Y. T. Wu Y. J. Tetrahedron 2015 71 9258.
doi: 10.1016/j.tet.2015.10.035 |
[19] |
Qiu F. C. Yang W. C. Chang Y. Z. Guan B. T. Asian J. Org. Chem. 2017 6 1361.
doi: 10.1002/ajoc.201700238 |
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