SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 5: 1675 - 1685

DOI: https://doi.org/10.6023/cjoc202312018

ARTICLES

Visible Light-Induced Decarbon-Carboxylation of Activated Alkenes by Carbon Dioxide

  • Dongsen Duan ,
  • Yuan Ma ,
  • Yubo Liu ,
  • Fu Cheng ,
  • Daoyong Zhu ,
  • Shaohua Wang
Expand
  • State Key Laboratory of Applied Organic Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 730000
*E-mail: ;

Received date: 2023-12-18

  Revised date: 2023-12-21

  Online published: 2024-01-05

Supported by

National Key R&D Program of China(2023YFA1506404); Science and Technology Program of Gansu Province(23ZDFA003); Science and Technology Program of Gansu Province(23JRRA1144); Science and Technology Program of Gansu Province(23JRRA1028); Science and Technology Program of Gansu Province(23CXGA0043); Lanzhou Science and Technology Planning Project(2023-1-17); Lanzhou Science and Technology Planning Project(2023-QN-18); Fundamental Research Funds for the Central Universities(lzujbky-2022-ct03); Fundamental Research Funds for the Central Universities(lzujbky-2022-sp09); Fundamental Research Funds for the Central Universities(lzujbky-2023-ct02); Fundamental Research Funds for the Central Universities(lzujbky-2023-pd08); Collaborative Innovation Center for Northwestern Chinese Medicine of Lanzhou University and the Drug Research Project of Gansu Province(2022GSMPA0010)

Fold

Abstract

An efficient visible light-facilitated decarbon-carboxylation of activated alkenes has been successfully developed. Compared with traditional alkene carboxylation, this method features mild conditions, up to 96% yield and good compatibility with a variety of functional groups. It provides a new method for the synthesis of phenylacetic acid and its derivatives. The mechanism study shows that the reaction realizes the synthesis of the corresponding carboxylic acid with constant apparent carbon number by substituting the carbon-carbon double bond of alkene.

Key words： visible light induction; carbon dioxide; activated alkene; carboxylation

Cite this article

Dongsen Duan , Yuan Ma , Yubo Liu , Fu Cheng , Daoyong Zhu , Shaohua Wang . Visible Light-Induced Decarbon-Carboxylation of Activated Alkenes by Carbon Dioxide[J]. Chinese Journal of Organic Chemistry, 2024 , 44(5) : 1675 -1685 . DOI: 10.6023/cjoc202312018

References

[1]
(a) Sakakura, T.; Choi, J.-C.; Yasuda, H. Chem. Soc. Rev. 2011, 40, 2435.
[1]
(b) Liu, Q.; Wu, L.; Jackstell, R.; Beller, M. Nat. Commun. 2015, 6, 5933.
[1]
(c) Correa, A.; Martín, R. Angew. Chem., Int. Ed. 2009, 48, 6201.
[1]
(d) Tsuji, Y.; Fujihara, T. Chem. Commun. 2012, 48, 9956.
[1]
(e) B?rjesson, M.; Moragas, T.; Gallego, D.; Martin, R. ACS Catal. 2016, 6, 6739.
[1]
(f) Gui, Y.-Y.; Zhou, W.-J.; Ye, J.-H.; Yu, D.-G. ChemSusChem 2017, 10, 1337.
[1]
(g) Chen, K.-H.; Li, H.-R.; He, L.-N. Chin. J. Org. Chem. 2020, 40, 2195 (in Chinese).
[1]
( 陈凯宏, 李红茹, 何良年, 有机化学, 2020, 40, 2195.)
[1]
(h) Guo, X.; Wang, Y.-Z.; Chen, J.; Li, G.-Q.; Xia, J.-B. Chin. J. Org. Chem. 2020, 40, 2208 (in Chinese).
[1]
( 郭霄, 王亚洲, 陈洁, 李公强, 夏纪宝, 有机化学, 2020, 40, 2208.)
[1]
(i) Ye, J.-H.; Ju, Tao.; Huang, H.; Liao, L.-L.; Yu, D.-G. Acc. Chem. Res. 2021, 54, 2518.
[1]
(j) Dou, Q.; Wang, T.-M.; Li, S.-F.; Fang, L.-J.; Zhai, H.-B.; Cheng, B. Chin. J. Org. Chem. 2022, 42, 4257 (in Chinese).
[1]
( 窦谦, 汪太民, 李嗣锋, 房丽晶, 翟宏斌, 程斌, 有机化学, 2022, 42, 4257.)
[1]
(k) Wu, Z.-Q.; Fan, Z.-N.; Xi, C.-J. Chin. Sci. Bull. 2021, 66, 773.
[2]
(a) Han, ?. M.; Kü?ükgüzel, G. ?. Mini-Rev. Med. Chem. 2020, 20, 1300.
[2]
(b) Gouda, A. M.; Beshr, E. A.; Almalki, F. A.; Halawah, H. H.; Taj, B. F.; Alnafaei, A. F.; Alharazi, R. S.; Kazi, W. M.; AlMatrafi, M. M. Bioorg. Chem. 2019, 92, 103224.
[3]
(a) Zhong, J.-S.; Yang, Z.-X.; Ding, C.-L.; Huang, Y.-F.; Zhao, Y.; Yan, H.; Ye, K.-Y. J. Org. Chem. 2021, 86, 16162.
[3]
(b) Ran, C.-K.; Niu, Y.-N.; Song, L.; Wei, M.-K.; Cao, Y.-F.; Luo, S.-P.; Yu, Y.-M.; Liao, L.-L.; Yu, D.-G. ACS Catal. 2022, 12, 18.
[3]
(c) Yang, D.-T.; Zhu, M.; Schiffer, Z. J.; Williams, K.; Song, X.; Liu, X.; Manthiram, K. ACS Catal. 2019, 9, 4699.
[3]
(d) Correa, A.; León, T.; Martin, R. J. Am. Chem. Soc. 2014, 136, 1062.
[3]
(e) Li, W.-D.; Wu, Y.; Li, S.-J.; Jiang, Y.-Q.; Li, Y.-L.; Lan, Y.; Xia, J.-B. J. Am. Chem. Soc. 2022, 144, 8551.
[3]
(f) Grigg, R. D.; Rigoli, J. W.; Van Hoveln, R.; Neale, S.; Schomaker, J. M. Chem.-Eur. J. 2012, 18, 9391.
[3]
(g) Moragas, T.; Gaydou, M.; Martin, R. Angew. Chem., Int. Ed. 2016, 55, 5053.
[3]
(h) Wang, L.; Li, T.; Perveen, S.; Zhang, S.; Wang, X.; Ouyang, Y.; Li, P. Angew. Chem., Int. Ed. 2022, 61, e202213943.
[3]
(i) Yang, H.-P.; Lin, Q.; Zhang, H.-W.; Li, G.-D.; Fan, L.-D.; Chai, X.-Y.; Zhang, Q.-L.; Liu, J.-H.; He, C.-X. Chem. Commun. 2018, 54, 4108.
[3]
(j) Chen, B.-L.; Zhu, H.-W.; Xiao, Y.; Sun, Q.-L.; Wang, H.; Lu, J.-X. Electrochem. Commun. 2014, 42, 55.
[3]
(k) Jing, K.; Wei, M.-K.; Yan, S.-S.; Liao, L.-L.; Niu, Y.-N.; Luo, S.-P.; Yu, B.; Yu, D.-G. Chin. J. Catal. 2022, 43, 1667.
[3]
(l) Yan, S.-S.; Liu, S.-H.; Chen, L.; Bo, Z.-Y.; Jing, K.; Gao, T.-Y.; Yu, B.; Lan, Y.; Luo, S.-P.; Yu, D.-G. Chem 2021, 7, 3099.
[4]
(a) Meng, Q.-Y.; Schirmer, T. E.; Berger, A. L.; Donabauer, K.; K?nig, B. J. Am. Chem. Soc. 2019, 141, 11393.
[4]
(b) Ishida, N.; Masuda, Y.; Imamura, Y.; Yamazaki, K.; Murakami, M. J. Am. Chem. Soc. 2019, 141, 19611.
[4]
(c) Lee, H.-J.; Kim, H.; Kim, D.-P. Chem.-Eur. J. 2019, 25, 11641.
[4]
(d) Faigl, F.; Schlosser, M. Tetrahedron Lett. 1991, 32, 3369.
[5]
(a) Jin, Y.; Caner, J.; Nishikawa, S.; Toriumi, N.; Iwasawa, N. Nat. Commun. 2022, 13, 7584.
[5]
(b) Shao, P.; Wang, S.; Chen, C.; Xi, C. Org. Lett. 2016, 18, 2050.
[5]
(c) Martin, A. C.; Rogers, J. A.; Batsomboon, P.; Morrison, A. E.; Ramsubhag, R. R.; Popp, B. V.; Dudley, G. B. ACS Omega 2021, 6, 30108.
[5]
(d) Saini, S.; Singh, H.; Prajapati, P. K.; Sinha, A. K.; Jain, S. L. ACS Sustainable Chem. Eng. 2019, 7, 11313.
[5]
(e) Greenhalgh, M. D.; Thomas, S. P. J. Am. Chem. Soc. 2012, 134, 11900.
[5]
(f) Williams, C. M.; Johnson, J. B.; Rovis, T. J. Am. Chem. Soc. 2008, 130, 14936.
[5]
(g) Gaydou, M.; Moragas, T.; Juliá-Hernández, F.; Martin, R. J. Am. Chem. Soc. 2017, 139, 12161.
[5]
(h) Meng, Q.-Y.; Wang, S.; Huff, G. S.; K?nig, B. J. Am. Chem. Soc. 2018, 140, 3198.
[5]
(i) Greenhalgh, M. D.; Kolodziej, A.; Sinclair, F.; Thomas, S. P. Organometallics 2014, 33, 5811.
[5]
(j) Kawashima, S.; Aikawa, K.; Mikami, K. Eur. J. Org. Chem. 2016, 2016, 3166.
[5]
(k) Murata, K.; Numasawa, N.; Shimomaki, K.; Takaya, J.; Iwasawa, N. Chem. Commun. 2017, 53, 3098.
[6]
(a) Niu, Y.-N.; Jin, X.-H.; Liao, L.-L.; Huang, H.; Yu, B.; Yu, Y.-M.; Yu, D.-G. Sci. China: Chem. 2021, 64, 1164.
[6]
(b) Fu, Q.; Bo, Z.-Y.; Ye, J.-H.; Ju, T.; Huang, H.; Liao, L.-L.; Yu, D.-G. Nat. Commun. 2019, 10, 3592.
[6]
(c) Ju, T.; Zhou, Y.-Q.; Cao, K.-G.; Fu, Q.; Ye, J.-H.; Sun, G.-Q.; Liu, X.-F.; Chen, L.; Liao, L.-L.; Yu, D.-G. Nat. Catal. 2021, 4, 304.
[6]
(d) Senboku, H.; Komatsu, H.; Fujimura, Y.; Tokuda, M. Synlett 2001, 2001, 0418.
[6]
(e) Knowlden, S. W.; Popp, B. V. Organometallics 2022, 41, 1883.
[6]
(f) Zhou, C.; Li, M.; Sun, J.; Cheng, J.; Sun, S. Org. Lett. 2021, 23, 2895.
[6]
(g) Butcher, T. W.; McClain, E. J.; Hamilton, T. G.; Perrone, T. M.; Kroner, K. M.; Donohoe, G. C.; Akhmedov, N. G.; Petersen, J. L.; Popp, B. V. Org. Lett. 2016, 18, 6428.
[6]
(h) Xu, P.; Wang, S.; Xu, H.; Liu, Y.-Q.; Li, R.-B.; Liu, W.-W.; Wang, X.-Y.; Zou, M.-L.; Zhou, Y.; Guo, D.; Zhu, X. ACS Catal. 2023, 13, 2149.
[6]
(i) Wang, H.; Gao, Y.; Zhou, C.; Li, G. J. Am. Chem. Soc. 2020, 142, 8122.
[6]
(j) Zhang, W.; Lin, S. J. Am. Chem. Soc. 2020, 142, 20661.
[6]
(k) Benedetti Vega, K.; Campos Delgado, J. A.; Pugnal, L. V. B. L.; K?nig, B.; Menezes Correia, J. T.; Weber Paix?o, M. Chem.-Eur. J. 2023, 29, e202203625.
[6]
(l) Yatham, V. R.; Shen, Y.; Martin, R. Angew. Chem., Int. Ed. 2017, 56, 10915.
[6]
(m) Tortajada, A.; Juliá-Hernández, F.; B?rjesson, M.; Moragas, T.; Martin, R. Angew. Chem., Int. Ed. 2018, 57, 15948.
[6]
(n) Wang, H.; Lin, M.-Y.; Fang, H.-J.; Chen, T.-T.; Lu, J.-X. Chin. J. Chem. 2007, 25, 913.
[6]
(o) Perrone, T. M.; Gregory, A. S.; Knowlden, S. W.; Ziemer, N. R.; Alsulami, R. N.; Petersen, J. L.; Popp, B. V. ChemCatChem 2019, 11, 5814.
[6]
(p) Louvel, D.; Souibgui, A.; Taponard, A.; Rouillon, J.; ben Mosbah, M.; Moussaoui, Y.; Pilet, G.; Khrouz, L.; Monnereau, C.; Vantourout, J. C.; Tlili, A. Adv. Synth. Catal. 2022, 364, 139.
[6]
(q) Shao, P.; Wang, S.; Chen, C.; Xi, C. Chem. Commun. 2015, 51, 6640.
[6]
(r) Dérien, S.; Clinet, J.-C.; Du?ach, E.; Périchon, J. Tetrahedron 1992, 48, 5235.
[6]
(s) Hou, J.; Ee, A.; Cao, H.; Ong, H.-W.; Xu, J.-H.; Wu, J. Angew. Chem., Int. Ed. 2018, 57, 17220.
[6]
(t) Liao, L.-L.; Cao, G.-M.; Jiang, Y.-X.; Jin, X.-H.; Hu, X.-L.; Chruma, J. J.; Sun, G.-Q.; Gui, Y.-Y.; Yu, D.-G. J. Am. Chem. Soc. 2021, 143, 2812.
[7]
Zhang, B.; Yi, Y.; Wu, Z.-Q.; Chen, C.; Xi, C. Green Chem. 2020, 22, 5961.
[8]
(a) Shi, A.; Sun, K.; Chen, X.; Qu, L.; Zhao, Y.; Yu, B. Org. Lett. 2022, 24, 299.
[8]
(b) Lu, Y.-H.; Mu, S.-Y.; Jiang, J.; Wu, C.; Zhou, M.-H.; Ouyang, W.-T.; He, W.-M. Green Chem. 2023, 25, 5539.
[8]
(c) Zeng, F. L.; Zhu, H. L.; Wang, R. N.; Yuan, X. Y.; Sun, K.; Qu, L. B.; Chen, X. L.; Yu, B. Chin. J. Catal. 2023, 46, 157.
[9]
Hahm, H.; Kim, J.; Ryoo, J. Y.; Han, M. S.; Hong, S. Org. Biomol. Chem. 2021, 19, 6301.
[10]
Wu, Z.; Gockel, S. N.; Hull, K. L. Nat. Commun. 2021, 12, 5956.
[11]
Cai, S.-Y.; Zhao, X.-Y.; Wang, X.-B.; Liu, Q.-S.; Li, Z.-S.; Wang, D. Z. Angew. Chem., Int. Ed. 2012, 51, 8050.
[12]
Yuan, P.-F.; Y, Z.; Zhang, S.-S.; Zhu, C.-M.; Yang, X.-L.; Meng, Q.-Y. Angew. Chem., Int. Ed. 2023, e202313030.
[13]
Liao, L.-L.; Cao, G.-M.; Ye, J.-H.; Sun, G.-Q.; Zhou, W.-J.; Gui, Y.-Y.; Yan, S.-S.; Shen, G.; Yu, D.-G. J. Am. Chem. Soc. 2018, 140, 17338.
[14]
Chang, J.; Xie, W.; Wang, L.; Ma, N.; Cheng, S.; Xie, J. Eur. J. Med. Chem. 2006, 41, 397.
[15]
Hang, W.; Li, D.; Zou, S.; Xi, C. J. Org. Chem. 2023, 88, 5007.
[16]
Babin, V.; Talbot, A.; Labiche, A.; Destro, G.; Del Vecchio, A.; Elmore, C. S.; Taran, F.; Sallustrau, A.; Audisio, D. ACS Catal. 2021, 11, 2968.
[17]
Bazzi, S.; Schulz, E.; Mellah, M. Org. Lett. 2019, 21, 10033.
[18]
Niwayama, S.; Cho, H.; Lin, C. Tetrahedron Lett. 2008, 49, 4434.
[19]
Linhardt, R. J.; Murr, B. L.; Montgomery, E.; Osby, J.; Sherbine, J. J. Org. Chem. 1982, 47, 2242.
[20]
Gevorgyan, A.; Obst, M. F.; Guttormsen, Y.; Maseras, F.; Hopmann, K. H.; Bayer, A. Chem. Sci. 2019, 10, 10072.
[21]
Pquette, L. A.; Maynard, G. D. J. Org. Chem. 1989, 54, 5054.
[22]
Wright, S. W.; Hageman, D. L.; McClure, L. D. J. Org. Chem. 1994, 59, 6095.
Options
Outlines

/

〈 〉