Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (10): 3159-3168.DOI: 10.6023/cjoc202406038 Previous Articles Next Articles
Special Issue: 二氧化碳专题合集
ARTICLES
收稿日期:
2024-06-27
修回日期:
2024-09-05
发布日期:
2024-09-18
基金资助:
Aolong Zhang, Han Yang, Peidong Cheng, Yang Yao, Song Sun*()
Received:
2024-06-27
Revised:
2024-09-05
Published:
2024-09-18
Contact:
*E-mail: Supported by:
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Aolong Zhang, Han Yang, Peidong Cheng, Yang Yao, Song Sun. Visible-Light Photoredox-Catalyzed Carbon/Carboxylation of Alkenes with Malonates and CO2[J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3159-3168.
Entry | Catalyst | Base | Solvent | 3aa yieldb/% |
---|---|---|---|---|
1 | PC1 | Na2CO3 | DMSO | 24 |
2 | PC2, PC3 | Na2CO3 | DMSO | <5 |
3 | PC4 | Na2CO3 | DMSO | 90 |
4 | PC4 | Cs2CO3 | DMSO | 62 |
5 | PC4 | K2CO3 | DMSO | 71 |
6 | PC4 | K3PO4 | DMSO | 65 |
7 | PC4 | Et3N | DMSO | N.R. |
8 | PC4 | Na2CO3 | DMF | 56 |
9 | PC4 | Na2CO3 | DMAc | 17 |
10 | PC4 | Na2CO3 | 1,4-Dioxane | N.R. |
11 | PC4 | Na2CO3 | MeCN | N.R. |
12 | PC4 | Na2CO3 | DMSO | 63c, 70d, 66e |
13 | PC4 | Na2CO3 | DMSO | 85f, 84g, 77h, 81i |
14 | PC4 | Na2CO3 | DMSO | 71j, 75k |
15l | PC4 | Na2CO3 | DMSO | 0 |
16m | PC4 | Na2CO3 | DMSO | 91 |
Entry | Catalyst | Base | Solvent | 3aa yieldb/% |
---|---|---|---|---|
1 | PC1 | Na2CO3 | DMSO | 24 |
2 | PC2, PC3 | Na2CO3 | DMSO | <5 |
3 | PC4 | Na2CO3 | DMSO | 90 |
4 | PC4 | Cs2CO3 | DMSO | 62 |
5 | PC4 | K2CO3 | DMSO | 71 |
6 | PC4 | K3PO4 | DMSO | 65 |
7 | PC4 | Et3N | DMSO | N.R. |
8 | PC4 | Na2CO3 | DMF | 56 |
9 | PC4 | Na2CO3 | DMAc | 17 |
10 | PC4 | Na2CO3 | 1,4-Dioxane | N.R. |
11 | PC4 | Na2CO3 | MeCN | N.R. |
12 | PC4 | Na2CO3 | DMSO | 63c, 70d, 66e |
13 | PC4 | Na2CO3 | DMSO | 85f, 84g, 77h, 81i |
14 | PC4 | Na2CO3 | DMSO | 71j, 75k |
15l | PC4 | Na2CO3 | DMSO | 0 |
16m | PC4 | Na2CO3 | DMSO | 91 |
[1] |
For selected typical reviews, please see: (a) Sakakura, T.; Choi, J.-C.; Yasuda, H. Chem. Rev. 2007, 107, 2365.
pmid: 21887758 |
(b) He, M.; Sun, Y.; Han, B. Angew. Chem. Int. Ed. 2022, 61, e202112835.
pmid: 21887758 |
|
(c) Cokoja, M.; Bruckmeier, C.; Rieger, B.; Herrmann, W. A.; Kühn, F. E. Angew. Chem. Int. Ed. 2011, 50, 8510.
doi: 10.1002/anie.201102010 pmid: 21887758 |
|
(d) Jia, S.; Ma, X.; Sun, X.; Han, B. CCS Chem. 2022, 4, 3213.
pmid: 21887758 |
|
[2] |
(a) Qiu, L.-Q.; Yao, X.; Zhang, Y.-K.; Li, H.-R.; He, L.-N. J. Org. Chem. 2023, 88, 4942.
pmid: 17447821 |
(b) Wang, S.; Xi, C. Chem. Soc. Rev. 2019, 48, 382.
pmid: 17447821 |
|
(c) Pimparkar, S.; Dalvi, A. K.; Koodan, A.; Maiti, S.; Al-Thabaiti, S.; Mokhtar, M.; Dutta, A.; Lee, Y. R.; Maiti, D. Green Chem. 2021, 23, 9283.
pmid: 17447821 |
|
(d) Guo, Y.; Wei, L.; Wen, Z.; Qi, C.; Jiang, H. Acta Phys.-Chim. Sin. 2024, 40, 2307004.
pmid: 17447821 |
|
(e) Wang, Q.; Wang, Y.; Liu, M.; Chu, G.; Qiu, Y. Chin. J. Chem. 2024, 42, 2249.
pmid: 17447821 |
|
(f) Lanzia, M.; Kleij, A. W. Chin. J. Chem. 2024, 42, 430.
pmid: 17447821 |
|
(g) Sekine, K.; Yamada, T. Chem. Soc. Rev. 2016, 45, 4524.
doi: 10.1039/c5cs00895f pmid: 17447821 |
|
(f) Li, Y.; Cui, X.; Dong, K.; Junge, K.; Beller, M. ACS Catal. 2017, 7, 1077.
pmid: 17447821 |
|
(g) Darensbourg, D. J. Chem. Rev. 2007, 107, 2388.
pmid: 17447821 |
|
[3] |
For selected typical reviews, please see: (a) Wang, S.; Du, G.; Xi, C. Org. Biomol. Chem. 2016, 14, 3666.
pmid: 35921535 |
(b) Mao, B.; Wei, J.-S.; Shi, M. Chem. Commun. 2022, 58, 9312.
pmid: 35921535 |
|
(c) Liu, Q.; Wu, L.; Jackstell, R.; Beller, M. Nat. Commun. 2015, 6, 5933.
pmid: 35921535 |
|
For selected typical examples, please see: (d) Jiang, Y.-X.; Liao, L.-L.; Gao, T.-Y.; Xu, W.-H.; Zhang, W.; Song, L.; Sun, G.-Q.; Ye, J.-H.; Lan, Y.; Yu, D.-G. Nat. Synth. 2024, 3, 394.
pmid: 35921535 |
|
(e) Yu, B.; Liu, Y.; Xiao, H.-Z.; Li, C.-F.; Ye, J.-H.; Yu, D.-G. Chem. 2024, 10, 938.
pmid: 35921535 |
|
(f) Sun, G.-Q.; Yu, P.; Zhang, W.; Zhang, W.; Wang, Y.; Liao, L.-L.; Zhang, Z.; Li, L.; Lu, Z.; Yu, D.-G.; Lin, S. Nature 2023, 615, 67.
pmid: 35921535 |
|
(g) Zhang, K.; Ren, B.-H.; Liu, X.-F.; Wang, L.-L.; Zhang, M.; Ren, W.-M.; Lu, X.-B.; Zhang, W.-Z. Angew. Chem., Int. Ed. 2022, e202207660.
pmid: 35921535 |
|
(h) Yuan, P.-F.; Yang, Z.; Zhang, S.-S.; Zhu, C.-M.; Yang, X.-L.; Meng, Q.-Y. Angew. Chem., Int. Ed. 2023, e202313030.
pmid: 35921535 |
|
(i) Sha, Y.; Bai, J.; Li, M.; Gao, W.; Yang, Q.; Sun, J.; Sun, S. Org. Lett. 2022, 24, 5715.
doi: 10.1021/acs.orglett.2c02123 pmid: 35921535 |
|
[4] |
(a) Ohishi, T.; Nishiura, M.; Hou, Z. Angew. Chem., Int. Ed. 2008, 47, 5792.
|
(b) Yeung, C. S.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 7826.
|
|
[5] |
(a) Manjolinho, F.; Arndt, M.; Gooßen, K.; Gooßen, L. J. ACS Catal. 2012, 2, 2014.
|
(b) Schmalzbauer, M.; Svejstrup, T. D.; Fricke, F.; Brandt, P.; Johansson, M. J.; Bergonzini, G.; König, B. Chem 2020, 6, 2658.
|
|
(c) Wang, L.; Wu, H.; Zhao, Y.; Li, B.; Wang, B. Org. Lett. 2024, 26, 3940.
|
|
(d) Mizuno, H.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2011, 133, 1251.
|
|
(e) Meng, Q.-Y.; Schirmer, T. E.; Berger, A. L.; Donabauer, K.; König, B. J. Am. Chem. Soc. 2019, 141, 11393.
|
|
(f) Sahoo, H.; Zhang, L.; Cheng, J.; Nishiura, M.; Hou, Z. J. Am. Chem. Soc. 2022, 144, 23585.
|
|
[6] |
(a) Tortajada, A.; Börjesson, M.; Martin, R. Acc. Chem. Res. 2021, 54, 3941.
pmid: 38193812 |
(b) Chen, X.-W.; Li, C.; Gui, Y.-Y.; Yue, J.-P.; Zhou, Q.; Liao, L.-L.; Yang, J.-W.; Ye, J.-H.; Yu, D.-G. Angew. Chem., Int. Ed. 2024, e202403401.
pmid: 38193812 |
|
(c) Chen, X.-W.; Yue, J.-P.; Wang, K.; Gui, Y.-Y.; Niu, Y.-N.; Liu, J.; Ran, C.-K.; Kong, W.; Zhou, W.-J.; Yu, D.-G. Angew. Chem., Int. Ed. 2021, 60, 14068.
pmid: 38193812 |
|
(d) Davies, J.; Lyonnet, J. R.; Carvalho, B.; Sahoo, B.; Day, C. S.; Juliá-Hernández, F.; Duan, Y.; Velasco-Rubio, Á.; Obst, M.; Norrby, P.-O.; Hopmann, K. H.; Martin, R. J. Am. Chem. Soc. 2024, 146, 1753.
doi: 10.1021/jacs.3c11205 pmid: 38193812 |
|
(e) Tang, S.; Liu, Z.; Zhang, J.; Li, B.; Wang, B. Angew. Chem., Int. Ed. 2024, e202318572.
pmid: 38193812 |
|
[7] |
(a) Xiong, W.; Shi, F.; Cheng, R.; Zhu, B.; Wang, L.; Chen, P.; Lou, H.; Wu, W.; Qi, C.; Lei, M.; Jiang, H. ACS Catal. 2020, 10, 7968.
pmid: 31960672 |
(b) Gaydou, M.; Moragas, T.; Juliá-Hernández, F.; Martin, R. J. Am. Chem. Soc. 2017, 139, 12161.
pmid: 31960672 |
|
(c) Catherine, M.; Williams, C. M.; Johnson, J. B.; Rovis, T. J. Am. Chem. Soc. 2008, 130, 14936.
doi: 10.1021/ja8062925 pmid: 31960672 |
|
(d) Alkayal, A.; Tabas, V.; Montanaro, S.; Wright, I. A.; Malkov, A. V.; Buckley, B. R. J. Am. Chem. Soc. 2020, 142, 1780.
doi: 10.1021/jacs.9b13305 pmid: 31960672 |
|
(e) Bertuzzi, G.; Cerveri, A.; Lombardi, L.; Bandini, M. Chin. J. Chem. 2021, 39, 3116.
pmid: 31960672 |
|
(f) Wang, M.-M.; Lu, S.-M.; Li, C. ACS Catal. 2022, 12, 10801.
pmid: 31960672 |
|
(g) Xu, P.; Xu, H.; Wang, S.; Hao, T.-Z.; Yan, S.-Y.; Guo, D.; Zhu, X. Org. Chem. Front. 2023, 10, 2013.
pmid: 31960672 |
|
(h) Ran, C.-K.; Xiao, H.-Z.; Liao, L.-L.; Ju, T.; Zhang, W.; Yu, D.-G. National Sci. Open 2022, 2, 20220024.
pmid: 31960672 |
|
[8] |
(a) He, X.; Qiu, L.-Q.; Wang, W.-J.; Chen, K.-H.; He, L.-N. Green Chem. 2020, 22, 7301.
|
(b) Ye, J.-H.; Ju, T.; Huang, H.; Liao, L.-L.; Yu, D.-G. Acc. Chem. Res. 2021, 54, 2518.
|
|
(c) Zhang, Z.; Ye, J.-H.; Ju, T.; Liao, L.-L.; Huang, H.; Gui, Y.-Y.; Zhou, W.-J.; Yu, D.-G. ACS Catal. 2020, 10, 10871.
|
|
[9] |
(a) Fu, Q.; Bo, Z.-Y.; Ye, J.-H.; Ju, T.; Huang, H.; Liao, L.-L.; Yu, D.-G. Nature Commun. 2019, 10, 3592.
|
(b) Yue, J.-P.; Xu, J.-C.; Luo, H.-T.; Chen, X.-W.; Song, H.-X.; Deng, Y.; Yuan, L.; Ye, J.-H.; Yu, D.-G. Nat. Catal. 2023, 6, 959.
|
|
[10] |
Yatham, V. R.; Shen, Y.; Martin, R. Angew. Chem., Int. Ed. 2017, 56, 10915.
|
[11] |
(a) Bai, J.; Li, M.; Zhou, C.; Sha, Y.; Cheng, J.; Sun, J.; Sun, S. Org. Lett. 2021, 23, 9654.
pmid: 32309942 |
(b) Wang, H.; Gao, Y.; Zhou, C.; Li, G. J. Am. Chem. Soc. 2020, 142, 8122.
doi: 10.1021/jacs.0c03144 pmid: 32309942 |
|
(c) Hou, J.; Ee, A.; Cao, H.; Ong, H.-W.; Xu, J.-H.; Wu, J. Angew. Chem., Int. Ed. 2018, 57, 17220.
pmid: 32309942 |
|
(d) Ye, J.-H.; Miao, M.; Huang, H.; Yan, S.-S.; Yin, Z.-B.; Zhou, W.-J.; Yu, D.-G. Angew. Chem., Int. Ed. 2017, 56, 15416.
pmid: 32309942 |
|
(e) Zhang, B.; Yi, Y.; Wu, Z.-Q.; Chen, C.; Xi, C. Green Chem. 2020, 22, 5961.
pmid: 32309942 |
|
[12] |
(a) Dénès, F.; Pérez-Luna, A.; Chemla, F. Chem. Rev. 2010, 110, 2366.
|
(b) Reddy, C. R.; Prasad, A. S.; Ajaykumar, U. Org. Lett. 2024, 26, 4904.
|
|
[13] |
Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672.
|
[14] |
(a) Hou, H.; Pan, Y.; Sun, Y.; Han, Y.; Yan, C.; Shi, Y.; Zhu, S. Chem. Eur. J. 2023, 29, e202301633.
pmid: 37846890 |
(b) Yamashita, Y.; Ogasawara, Y.; Banik, T.; Kobayashi, S. J. Am. Chem. Soc. 2023, 145, 23160.
doi: 10.1021/jacs.3c07436 pmid: 37846890 |
|
(c) Zhu, S.; Sun, Y.; Pan, Y.; Chen, X.; Yu, H.; Han, Y.; Yan, C.; Shi, Y.; Hou, H. J. Org. Chem. 2023, 88, 16639.
pmid: 37846890 |
|
(d) Dong, M.-Y.; Han, C.-Y.; Li, D.-S.; Hong, Y.; Liu, F.; Deng, H.-P. ACS Catal. 2022, 12, 9533.
pmid: 37846890 |
|
(e) White, D. R.; Hinds, E. M.; Bornowski, E. C.; Wolfe, J. P. Org. Lett. 2019, 21, 3813.
pmid: 37846890 |
|
[15] |
Hong, Y.; Dong, M.-Y.; Li, D.-S.; Deng, H.-P. Org. Lett. 2022, 24, 7677.
|
[16] |
Baś, S.; Yamashita, Y.; Kobayashi, S. ACS Catal. 2020, 10, 10546.
|
[17] |
Li, T.; Wang, W.; Dong, M.; Zhang, Z.; Yu, S.; Chen, Z.; Wei, S.; Yi, D. Chin. J. Chem. 2024, 42, 957.
|
[18] |
(a) Zhou, C.; Li, M.; Sun, J.; Cheng, J.; Sun, S. Org. Lett. 2021, 23, 2895.
pmid: 38747692 |
(b) Gao, W.; Yang, Q.; Yang, H.; Yao, Y.; Bai, J.; Sun, J.; Sun, S. Org. Lett. 2024, 26, 467.
pmid: 38747692 |
|
(c) Yang, H.; Yao, Y.; Yang, Q.; Yao, Y.; Sun, J.; Sun, S. Org. Lett. 2024, 26, 4194.
doi: 10.1021/acs.orglett.4c00841 pmid: 38747692 |
|
[19] |
Cheng, Z.; Jin, W.; Liu, C. Org. Chem. Front. 2019, 6, 841.
doi: 10.1039/c8qo01412d |
[20] |
(a) Speckmeier, E.; Fischer, T. G.; Zeitler, K. J. Am. Chem. Soc. 2018, 140, 15353.
doi: 10.1021/jacs.8b08933 pmid: 30277767 |
(b) Leitch, J. A.; Rogova, T.; Duarte, F.; Dixon, D. J. Angew. Chem., Int. Ed. 2020, 59, 4121.
pmid: 30277767 |
|
(c) Zhang, J.; Li, Y.; Zhang, F.; Hu, C.; Chen, Y. Angew. Chem., Int. Ed. 2016, 55, 1872.
pmid: 30277767 |
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