Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4476-4483.DOI: 10.6023/cjoc202106017 Previous Articles Next Articles
ARTICLES
收稿日期:
2021-06-08
修回日期:
2021-07-13
发布日期:
2021-07-26
通讯作者:
刘丙贤
基金资助:
Yuqian Dai, Xingwei Li, Bingxian Liu()
Received:
2021-06-08
Revised:
2021-07-13
Published:
2021-07-26
Contact:
Bingxian Liu
Supported by:
Share
Yuqian Dai, Xingwei Li, Bingxian Liu. Rh(III)-Catalyzed Efficient Synthesis of Isocoumarins from Cyclohexanediones[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4476-4483.
Entry | Base (2.5 equiv.) | Solvent (1 mL) | Yield/% |
---|---|---|---|
1 | — | HFIP | 65% |
2b | — | HFIP | n.d. |
3 | — | acetone | n.d. |
4 | — | THF | n.d. |
5 | — | DCE | n.d. |
6 | — | EA | n.d. |
7 | — | TFE | n.d. |
8 | — | EtOH | n.d. |
9 | KOH | HFIP | 54% |
10 | NaOAc | HFIP | 32% |
11 | K2CO3 | HFIP | 28% |
12 | LiOH | HFIP | 10% |
13 | NaOMe | HFIP | 28% |
14 | LiOtBu | HFIP | 26% |
15 | K3PO4 | HFIP | 96% |
16c | K3PO4 | HFIP | n.d. |
17 | |
Entry | Base (2.5 equiv.) | Solvent (1 mL) | Yield/% |
---|---|---|---|
1 | — | HFIP | 65% |
2b | — | HFIP | n.d. |
3 | — | acetone | n.d. |
4 | — | THF | n.d. |
5 | — | DCE | n.d. |
6 | — | EA | n.d. |
7 | — | TFE | n.d. |
8 | — | EtOH | n.d. |
9 | KOH | HFIP | 54% |
10 | NaOAc | HFIP | 32% |
11 | K2CO3 | HFIP | 28% |
12 | LiOH | HFIP | 10% |
13 | NaOMe | HFIP | 28% |
14 | LiOtBu | HFIP | 26% |
15 | K3PO4 | HFIP | 96% |
16c | K3PO4 | HFIP | n.d. |
17 | |
[1] |
(a) Schwartz, B. D.; Banwell, M. G.; Cade, I. A. Tetrahedron Lett. 2011, 52, 4526.
doi: 10.1016/j.tetlet.2011.06.050 pmid: 27597418 |
(b) Yang, S.; Banwell, M. G.; Willis, A. C.; Ward, J. S. Aust. J. Chem. 2015, 68, 241.
doi: 10.1071/CH14520 pmid: 27597418 |
|
(c) Ibn-Ahmed, S.; Khaldi, M.; Chrétien, F.; Chapleur, Y. J. Org. Chem. 2004, 69, 6722.
pmid: 27597418 |
|
(d) Ramanan, M.; Sinha, S.; Sudarshan, K.; Aidhen, I. S.; Doble, M. Eur. J. Med. Chem. 2016, 124, 428.
doi: S0223-5234(16)30724-3 pmid: 27597418 |
|
(e) Xu, X.; Li, J.; Zhang, K.; Wei, S.; Lin, R.; Polyak, S. W.; Yang, N.; Song, F. Mar. Drugs 2021, 19, 313.
doi: 10.3390/md19060313 pmid: 27597418 |
|
(f) Zhao, J.-Q.; Wang, Y.-M.; Wang, S.; Dang, J.; Shi, Y.-P.; Mei, L.-J.; Tao, Y.-D. Nat. Prod. Res. 2016, 30, 1746.
doi: 10.1080/14786419.2015.1137574 pmid: 27597418 |
|
[2] |
Akagi, Y.; Yamada, S.; Etomi, N.; Kumamoto, T.; Nakanishi, W.; Ishikawa, T. Tetrahedron Lett. 2010, 51, 1338.
doi: 10.1016/j.tetlet.2010.01.014 |
[3] |
(a) Ashraf, Z. Chem. Heterocycl. Compd. 2016, 52, 149.
doi: 10.1007/s10593-016-1849-z |
(b) Saikia, P.; Gogoi, S. Adv. Synth. Catal. 2018, 360, 2063.
doi: 10.1002/adsc.v360.11 |
|
[4] |
(a) Jiang, Y.; Li, P.; Zhao, J.; Liu, B.; Li, X. Org. Lett. 2020, 22, 7475.
doi: 10.1021/acs.orglett.0c02618 |
(b) Dong, Z.; Li, P.; Li, X.; Liu, B. Chin. J. Chem. 2021, 39, 3489.
|
|
[5] |
(a) Plunkett, S.; DeRatt, L. G.; Kuduk, S. D.; Balsells, J. Org. Lett. 2020, 22, 7662.
doi: 10.1021/acs.orglett.0c02851 pmid: 32969657 |
(b) Bryson, T. A.; Stewart, J. J.; Gibson, J. M.; Thomas, P. S.; Berch, J. K. Green Chem. 2003, 5, 174.
doi: 10.1039/b211966h pmid: 32969657 |
|
(c) Fan, X.; He, Y.; Cui, L.; Guo, S.; Wang, J.; Zhang, X. Eur. J. Org. Chem. 2012, 2012, 673.
pmid: 32969657 |
|
(d) Dong, F.; Liu, J.-Q.; Wang, X.-S. J. Heterocycl. Chem. 2019, 56, 2822.
doi: 10.1002/jhet.v56.10 pmid: 32969657 |
|
[6] |
(a) He, X.; Han, G.; Zuo, Y.; Shang, Y. Tetrahedron 2018, 74, 7082.
doi: 10.1016/j.tet.2018.10.045 |
(b) Yang, C.; He, X.; Zhang, L.; Han, G.; Zuo, Y.; Shang, Y. J. Org. Chem. 2017, 82, 2081.
doi: 10.1021/acs.joc.6b02906 |
|
(c) Li, Y.; Wang, Q.; Yang, X.; Xie, F.; Li, X. Org. Lett. 2017, 19, 3410.
doi: 10.1021/acs.orglett.7b01365 |
|
(d) Li, X. G.; Sun, M.; Liu, K.; Jin, Q.; Liu, P. N. Chem. Commun. 2015, 51, 2380.
doi: 10.1039/C4CC09314C |
|
(e) Zuo, Y.; He, X.; Ning, Y.; Zhang, L.; Wu, Y.; Shang, Y. New J. Chem. 2018, 42, 1673
doi: 10.1039/C7NJ03799F |
|
(f) Gao, C.; Li, B.; Geng, X.; Zhou, Q.; Zhang, X.; Fan, X. Green Chem. 2019, 21, 5113.
doi: 10.1039/C9GC02001B |
|
[7] |
(a) Mayakrishnan, S.; Tamizmani, M.; Maheswari, N. U. Chem. Commun. 2020, 56, 15462.
doi: 10.1039/D0CC06038K |
(b) Jia, M.; Ma, S. Angew. Chem., Int. Ed. 2016, 55, 9134.
doi: 10.1002/anie.v55.32 |
|
[8] |
Hong, C.; Jiang, X.; Yu, S.; Liu, Z.; Zhang, Y. Chin. J. Org. Chem. 2021, 41, 888. (in Chinese)
doi: 10.6023/cjoc202007037 |
(洪超, 蒋希程, 于书玲, 刘占祥, 张玉红, 有机化学, 2021, 41, 888.)
doi: 10.6023/cjoc202007037 |
|
[9] |
(a) Chen, Z.; Wang, B.; Zhang, J.; Yu, W.; Liu, Z.; Zhang, Y. Org. Chem. Front. 2015, 2, 1107.
doi: 10.1039/C5QO00004A pmid: 30033454 |
(b) Sambiagio, C.; Schonbauer, D.; Blieck, R.; Dao-Huy, T.; Pototschnig, G.; Schaaf, P.; Wiesinger, T.; Zia, M. F.; Wencel-Delord, J.; Besset, T.; Maes, B. U. W.; Schnurch, M. Chem. Soc. Rev. 2018, 47, 6603.
doi: 10.1039/c8cs00201k pmid: 30033454 |
|
[10] |
(a) Drapeau, M. P.; Gooßen, L. J. Chem.-Eur. J. 2016, 22, 18654.
doi: 10.1002/chem.v22.52 |
(b) Uttry, A.; Gemmeren, M. Synthesis 2020, 52, 479.
doi: 10.1055/s-0039-1690720 |
|
[11] |
Benzoyl chloride could react with the solvent to form the corresponding ester. Thus C―H activation can be realized by direction of ester group. The reaction can also occur by the use of pre-syn- thesized hexafluoroisopropyl benzoate, giving the product with 26% yield.
|
[12] |
(a) Park, S. H.; Kim, J. Y..; Chang, S. Org. Lett. 2011, 13, 2372.
doi: 10.1021/ol200600p |
(b) Yang, Y.; Lin, Y.; Rao, Y. Org. Lett. 2012, 14, 2874.
doi: 10.1021/ol301104n |
|
(c) Wang, S.-M.; Moku, B.; Leng, J.; Qin, H.-L. Eur. J. Org. Chem. 2018, 4407.
|
|
[13] |
Luo, J.; Fu, Q. Adv. Syn. Catal. 2021, 363, 3868.
doi: 10.1002/adsc.v363.16 |
[14] |
Tóth, B. L.; Monory, A.; Egyed, O.; Domján, A.; Bényei, A.; Szathury, B.; Novák, Z.; Stirling, A. Chem. Sci. 2021, 12, 5152.
doi: 10.1039/D1SC00642H |
[15] |
Sharma, K.; Neog, K.; Gogoi, P. Org. Lett. 2020, 22, 73.
doi: 10.1021/acs.orglett.9b03932 pmid: 31815487 |
[16] |
Jambu, S.; Jeganmohan, M. Org. Lett. 2020, 22, 5057.
doi: 10.1021/acs.orglett.0c01636 |
[1] | Jiling Yi, Kangqi Shi, Binglin Wu, Wanshan Li, Guangying Chen. Study on Secondary Metabolites of Marine-Derived Fungus Eutypella sp. F0219 [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 295-298. |
[2] | Fei Chen, Sheng Tao, Ning Liu, Bin Dai. CNN-Type Binuclear Cu(I) Complexes Catalyzed Direct Carboxylation via the Fixation of CO2 at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2471-2480. |
[3] | Cheng Gong, Jian Tang, Fei Xu, Pengjie Li, Zetian Wang, Yumin Zhang, Guoxian Yu, Liang Wang. Recent Advances in Transition-Metal-Catalyzed C—H Activation of Pyridone/Isoquinolones [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 1925-1949. |
[4] | Chengyao Kimmy Cao, Yaru Niu, Yunchen Jiang, Hongmei Qu, Chao Chen. Pd-Catalyzed Chlorodifluoroethylation Reaction of C—H Bond of Acetanilides with Chlorodifluoroethyl Iodonium Reagents [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2098-2105. |
[5] | Chaoyu Wang, Shuda Dong, Tianyang Zhu, Yuqin Liu, Zihan Wu, Ruokun Feng. Cobalt-Catalyzed Decarbonylative C(8)-Acyloxylation of 1-Naphthalamine Derivatives with α-Oxocarboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1799-1810. |
[6] | Xinyao Wang, Qingqing Zhang, Shuyang Liu, Min Li, Haifang Li, Chunying Duan, Yunhe Jin. Visible Light-Induced Metal-Free Benzylation of Quinones via Cross Dehydrogenation Coupling Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1443-1452. |
[7] | Yudong Li, Ying Li, Ya'nan Dong, Chungu Xia, Yuehui Li. Manganese-Catalyzed Allylation of Quinazolinones with 4-Vinyl-1,3-dioxolan-2-one via C—H Activation [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 847-853. |
[8] | Jiazhuang Wang, Liguo Teng, Shaoqi Xiong, Tiebo Xiao, Yubo Jiang. Rh-Catalyzed gem-Difluoroallylation of N-Tosylhydrazones [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3658-3667. |
[9] | Lingjie Fan, Tao Zhou, Xu Yang, Mengxue Jiang, Xinquan Hu, Bingfeng Shi. Pd(II)-Catalyzed Enantioselective C—H Olefination of 2-(Arylsulfinyl)pyridines through Kinetic Resolution [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3405-3418. |
[10] | Huanhuan Luo, Na Pei, Jing Zhang. Advances in Nitrogen-Directed Aromatic Compound ortho-C—H Bond Borylation Catalyzed by Transition Metals [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 2990-3001. |
[11] | Man Xu, Yuanzhi Xia. Mechanistic Understanding of Rh(III)-Catalyzed Redox-Neutral C—H Activation/Annulation Reactions of N-Phenoxyacetamides and Methyleneoxetanones [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3272-3278. |
[12] | Xiaoliang Zou, Senmiao Xu. Recent Progress in Iridium-Catalyzed Remote Regioselective C—H Borylation of (Hetero)Arenes [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2610-2620. |
[13] | Mingyang Sun, Kun Xu, Bingbing Guo, Chengchu Zeng. Copper-Catalyzed Vicinal C(sp2)—H Selenylation of Benzoic Acid Derivatives Using Air as Oxidant [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2302-2309. |
[14] | Ya-Lan Feng, Bing-Feng Shi. Recent Advances in Base Metal (Copper, Cobalt and Nickel)-Catalyzed Directed C—H Amination [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3753-3770. |
[15] | Fang Zhixing, Liu Juyan, Qiao Yanhong. Bromodimethylsulfonium Bromide Catalyzed Synthesis of Pyrazole-Fused Isocoumarins [J]. Chin. J. Org. Chem., 2018, 38(8): 1985-1992. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||