Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (5): 1576-1583.DOI: 10.6023/cjoc202310026 Previous Articles Next Articles
ARTICLES
张娟a, 王奕森a, 田钰a, 徐晶a, 高文超a, 常宏宏a,b,*(), 孟凡会c,*(), 杨朋d,*()
收稿日期:
2023-10-26
修回日期:
2023-12-24
发布日期:
2024-01-18
基金资助:
Juan Zhanga, Yisen Wanga, Yu Tiana, Jing Xua, Wenchao Gaoa, Honghong Changa,b(), Fanhui Mengc(), Peng Yangd()
Received:
2023-10-26
Revised:
2023-12-24
Published:
2024-01-18
Contact:
*E-mail: Supported by:
Share
Juan Zhang, Yisen Wang, Yu Tian, Jing Xu, Wenchao Gao, Honghong Chang, Fanhui Meng, Peng Yang. Regioselective C(2) Methylthiolation and d3-Methylthiolation of Indoles Based on Dimethyl Sulfoxide (DMSO-d6) Reagents[J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1576-1583.
Entry | [Cu] | Ligand | Oxidant | Yieldb/% |
---|---|---|---|---|
1 | CuI | dppp | TBPB | N.D. |
2 | CuBr | dppp | TBPB | N.D. |
3 | Cu(acac)2 | dppp | TBPB | Trace |
4 | Cu(OTf)2 | dppp | TBPB | N.D. |
5 | CuTc | dppp | TBPB | 36 |
6 | CuOAc | dppp | TBPB | 42 |
7 | Cu(OAc)2 | dppp | TBPB | 75 (62)c |
8 | Cu(OAc)2 | BINAP | TBPB | 35 |
9 | Cu(OAc)2 | PCy3 | TBPB | 43 |
10 | Cu(OAc)2 | dtbpy | TBPB | 38 |
11 | Cu(OAc)2 | dppp | MnO2 | Trace |
12 | Cu(OAc)2 | dppp | DTBP | 30 |
13 | Cu(OAc)2 | dppp | TBHP | 40 |
14 | dppp | TBPB | N.D. | |
15 | Cu(OAc)2 | TBPB | 23 | |
16 | Cu(OAc)2 | dppp | Trace |
Entry | [Cu] | Ligand | Oxidant | Yieldb/% |
---|---|---|---|---|
1 | CuI | dppp | TBPB | N.D. |
2 | CuBr | dppp | TBPB | N.D. |
3 | Cu(acac)2 | dppp | TBPB | Trace |
4 | Cu(OTf)2 | dppp | TBPB | N.D. |
5 | CuTc | dppp | TBPB | 36 |
6 | CuOAc | dppp | TBPB | 42 |
7 | Cu(OAc)2 | dppp | TBPB | 75 (62)c |
8 | Cu(OAc)2 | BINAP | TBPB | 35 |
9 | Cu(OAc)2 | PCy3 | TBPB | 43 |
10 | Cu(OAc)2 | dtbpy | TBPB | 38 |
11 | Cu(OAc)2 | dppp | MnO2 | Trace |
12 | Cu(OAc)2 | dppp | DTBP | 30 |
13 | Cu(OAc)2 | dppp | TBHP | 40 |
14 | dppp | TBPB | N.D. | |
15 | Cu(OAc)2 | TBPB | 23 | |
16 | Cu(OAc)2 | dppp | Trace |
[1] |
(a) Jiang, X. Sulfur Chemistry, Springer, Switzerland, 2019, p. 475.
pmid: 28418240 |
(b) Feng, M.; Tang, B.; Liang, H. S.; Jiang, X. Curr. Top. Med. Chem. 2016, 16, 1200.
pmid: 28418240 |
|
(c) Dunbar, K. L.; Scharf, D. H.; Litomska, A.; Hertweck, C. Chem. Rev. 2017, 117, 5521.
doi: 10.1021/acs.chemrev.6b00697 pmid: 28418240 |
|
(d) Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832.
pmid: 28418240 |
|
[2] |
(a) Wang, N.; Saidhareddy, P.; Jiang, X. Nat. Prod. Rep. 2020, 37, 246.
|
(b) Li, X.; Wang, X.; Li, Y.; Xiao, J.; Du, Y. Org. Biomol. Chem. 2022, 20, 4471.
|
|
[3] |
(a) Shen, C.; Qiao, J.; Zhao, L.; Zheng, K.; Jin, J.; Zhang, P. Catal. Commun. 2017, 92, 114.
|
(b) Li, H. L.; Kuninobu, Y.; Kanai, M. Angew. Chem., Int. Ed. 2017 129, 1517.
|
|
(c) Chen, S.; Guo, X.; Hou, H.; Geng, S.; Liu, Z.; He, Y.; Xue, X.; Feng, Z. Angew. Chem., Int. Ed. 2023, 62, e202303470.
|
|
[4] |
(a) Zhang, C.; Zhou, Y.; Huang, J.; Tu, C.; Zhou, X.; Yin, G. Org. Biomol. Chem. 2018, 16, 6316.
|
(b) Hu, L.; Wang, D.; Chen, X.; Yu, L.; Yu, Y.; Tan, Z.; Zhu, G. Org. Biomol. Chem. 2017, 15, 5674.
|
|
(c) Wang, M.; Qiao, Z.; Zhao, J.; Jiang, X. Org. Lett. 2018, 20, 6193.
|
|
(d) Zhang, B.; Li, X.; Li, X.; Sun, F.; Du, Y. Chin. J. Chem. 2020, 39, 887.
|
|
[5] |
(a) Chen, X.; Hao, X. S.; Goodhue, C. E.; Yu, J. Q. J. Am. Chem. Soc. 2006, 128, 6790.
|
(b) Dai, C.; Xu, Z.; Huang, F.; Yu, Z.; Gao, Y.-F. J. Org. Chem. 2012, 77, 4414.
|
|
(c) Chu, L.; Yue, X.; Qing, F.-L. Org. Lett. 2010, 12, 1644.
|
|
(d) Liu, F. Org. Biomol. Chem. 2023, 21, 1153.
|
|
[6] |
(a) Wu, X.-F.; Natteb, K. Adv. Synth. Catal. 2016, 358, 336.
|
(b) Tashrifi, Z.; Khanaposhtani, M. M.; Larijani, B.; Mahdavi, M. Adv. Synth. Catal. 2020, 362, 65.
doi: 10.1002/adsc.201901021 |
|
(c) Lu, H.; Tong, Z.; Peng, L.; Wang, Z.; Yin, S.-F.; Kambe, N.; Qiu, R. Top Curr. Chem. 2022, 380, 55.
|
|
[7] |
(a) Tian, Y.; Zhang, J. ; Gao, W.; Chang, H. Chin. J. Org. Chem. 2023, 43, 2391 (in Chinese).
|
( 田钰, 张娟, 高文超, 常宏宏, 有机化学, 2023, 43, 2391.)
|
|
(b) Sun, Q.; Soule, J.-F. Chem. Soc. Rev. 2021, 50, 10806.
|
|
[8] |
For review see: Li, X.; Wang, X.; Li, Y.; Xiao, J.; Du, Y. Org. Biomol. Chem. 2022, 20, 4471.
|
[9] |
(a) Zhang, Z.; Chen, P.; Liu, G. Chem. Soc. Rev. 2022, 51, 1640.
|
(b) Li, Z.-L. Fang, G.-C.; Gu, Q.-S.; Liu, X.-Y. Chem. Soc. Rev. 2020, 49, 32.
|
|
[10] |
(a) Zheng. C.; You. S.-L. Nat. Prod. Rep. 2019, 36, 1589.
doi: 10.1039/c8np00098k pmid: 25255204 |
(b) Leitch. J. A.; Bhonoah. Y.; Frost. C. G. ACS Catal. 2017, 7, 5618.
pmid: 25255204 |
|
(c) Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257.
doi: 10.1021/jm501100b pmid: 25255204 |
|
[11] |
(a) Ankade, S. B.; Shabade, A. B.; Soni, V.; Punji, B. ACS Catal. 2021, 11, 3268.
|
(b) Sandtorv, A. H. Adv. Synth. Catal. 2015, 357, 2403.
|
|
(c) Joucla, L.; Djakovitch, L. Adv. Synth. Catal. 2009, 351, 673.
|
|
(d) Wen, J.; Shi, Z. Acc. Chem. Res. 2021, 54, 1723.
|
|
(e) Liu, Y.-H.; Xie, P.-P.; Liu, L.; Fan, J.; Zhang, Z.-Z.; Hong, X.; Shi, B.-F. J. Am. Chem. Soc. 2021, 143, 19112.
|
|
[12] |
(a) Gensch, T.; Klauck, F. J. R.; Glorius, F. Angew. Chem., Int. Ed. 2016, 55, 11287.
|
(b) Zou, J.-F.; Huang, W.-S.; Li, L.; Xu, Z.; Zheng, Z.-J.; Yang, K.-F.; Xu, L.-W. RSC Adv. 2015, 5, 30389.
|
|
[13] |
Wu, Y.; Ding, H.; Zhao, M.; Ni, Z.-H.; Cao, J.-P. Green Chem. 2020, 22, 4906.
|
[14] |
Zhang, L.-Y.; Wu, Y.-H.; Wang, N.-X.; Gao, X.-W.; Yan, Z.; Xu, B.-C.; Liu, N.; Wang, B.-Z.; Xing, Y. Eur. J. Org. Chem. 2021, 2021, 1446.
|
[15] |
Sharma, P.; Rohilla, S.; Jain, N. J. Org. Chem. 2015, 80, 4116.
|
[16] |
Huang, J.; Sun, W.-W.; Li, J.-Q.; Ma, A.-D.; Liu, J.-K.; Wu, B. Org. Lett. 2023, 25, 528.
doi: 10.1021/acs.orglett.2c04270 pmid: 36646633 |
[17] |
(a) Barreiro, E. J.; Kümmerle, A. E.; Fraga, C. A. M. Chem. Rev. 2011, 111, 5215.
doi: 10.1021/cr200060g pmid: 24151256 |
(b) Schönherr, H.; Cernak, T. Angew. Chem., Int. Ed. 2013, 52, 12256.
doi: 10.1002/anie.201303207 pmid: 24151256 |
|
[18] |
Goyal, V.; Sarki, N.; Narani, A.; Naik, G.; Natte, K.; Jagadeesh, R. V. Coord. Chem. Rev. 2023, 474, 214827.
|
[19] |
Schmidt, C. Nat. Biotechnol. 2017, 35, 493.
|
[20] |
(a) Gao, Q.; Shang, Y.; Song, F.; Ye, J.; Liu, Z.-S.; Li, L.; Cheng, H.-G.; Zhou, Q. J. Am. Chem. Soc. 2019, 141, 15986.
|
(b) Wang, M.; Zhao, Y.; Zhao, Y.; Shi, Z. Sci. Adv. 2020, 6, eaba0946.
|
|
[21] |
(a) Cui, X.; Liu, X.; Wang, X.; Tian, W.; Wei, D.; Huang, G. ChemistrySelect 2017, 2, 8607.
|
(b) Dighe, S. U.; Samanta, S. K.; Kolle, S.; Batra, S. Tetrahedron 2017, 73, 2455.
|
|
[22] |
(a) Chen, Z.; Cao, G.; Zhang, F.; Li, H.; Xu, J.; Miao, M.; Ren, H. Synlett 2017, 28, 1795.
|
(b) Rastogi, G. K.; Deka, B.; Deb, M. L.; Baruah, P. K. Eur. J. Org. Chem. 2020, 2020, 424.
doi: 10.1002/ejoc.201901415 |
[1] | Yan Liu, Xiaomei Wang, Lin He, Shiwu Li, Zhifei Zhao. N-Heterocyclic Carbene (NHC)-Catalyzed [3+2] Cycloaddition to Highly Diastereoselective Synthesis of Spirooxindole Dihydrofuran Fused Pyrazolone Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1301-1310. |
[2] | Tianfeng Peng, Yuxiang Zhao, Shaojian Pu, Juan Luo, Teng Liu, Yingchun Miao, Xianfu Shen. Recent Advances in Total Synthesis of Prenylated Indole Alkaloids by Transition Metal-Catalyzed Reactions as the Key Step [J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1160-1180. |
[3] | Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408. |
[4] | Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245. |
[5] | Wenfeng Bei, Jian Pan, Dongmei Ran, Yilin Liu, Zhen Yang, Ruokun Feng. Cobalt-Catalyzed [4+2] Annulation of Indole Carboxamide with Diynes and Monoacetylene: Direct Access to γ-Carbolinones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3226-3238. |
[6] | Xiao Song, Jing Qing, Jun Li, Xuelei Jia, Fusong Wu, Junrong Huang, Jian Jin, Hengzhi You. Copper-Catalyzed Asymmetric Allyl Alkylation Using Grignard Reagents under Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3174-3179. |
[7] | Yingke Feng, He Wang, Mengxing Cui, Ran Sun, Xin Wang, Yang Chen, Lei Li. Visible-Light-Induced Difluoroalkylated Cyclization of Novel Functionalized Aromatic Isocyanides [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2913-2925. |
[8] | Yi Wang, Jian Zhang, Yangzi Liu, Xiaoyan Luo, Weiping Deng. Palladium-Catalyzed Asymmetric [3+4] Cycloadditions for the Construction of Cyclohepta[b]indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2864-2877. |
[9] | Yu Tian, Juan Zhang, Wenchao Gao, Honghong Chang. Application of Dimethyl Sulfoxide as Methylating Reagent in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2391-2406. |
[10] | Lixing Sun, Tingting Sun, Haiqing Wang, Shufang Wu, Xiaoye Wang, Tianya Liu, Yuchen Zhang. Lewis Acid-Catalyzed [2+4] Cyclization of 3-Alkyl-2-vinylindoles with α,β-Unsaturated N-Sulfonyl Ketimines [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2178-2188. |
[11] | Zeren Sun, Bingxin Zhai, Guangchao He, Hui Shen, Linya Chen, Shan Zhang, Yi Zou, Qihua Zhu, Yungen Xu. Synthesis and Anti-inflammatory Evaluation of Novel 1,2,3-Triazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2143-2155. |
[12] | Xiaoyu Lu, Xiaomei Sun, Yaqing Niu, Junchao Wang, Wenjing Yin, Mengting Gao, Zi Liu, Zhenghuan Wei, Tinghua Tao. Copper-Catalyzed Decarboxylative Cross-Coupling of α‑Fluoroacrylic Acids with N-Tosyl Oxaziridines [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2110-2119. |
[13] | Zhicheng Bao, Muyao Li, Jianbo Wang. Copper-Catalyzed Cross-Coupling of Aryldiazoacetates with Bis[(pinacolato)boryl]methane [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1808-1814. |
[14] | Chunsheng Li, Xiaoqi Lian, Lianfen Chen. Copper-Catalyzed [4+2] Annulations of Sulfoxonium Ylides and o-Phenylenediamines [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1492-1498. |
[15] | Yang Liu, Xiang Huang, Min Wang, Jian Liao. Enantioselective Copper-Catalyzed Mannich-Type Reaction of Cycic Ketimines and β,γ-Unsaturated N-Acylpyrazoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1499-1509. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||