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

doi:10.6023/cjoc202312018

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (5): 1675-1685.DOI: 10.6023/cjoc202312018 Previous Articles Next Articles

ARTICLES

可见光诱导的二氧化碳对活化烯烃的脱碳羧基化反应

段东森, 马媛, 刘宇博, 程富, 朱道勇^*(), 王少华^*()

兰州大学药学院功能有机分子化学国家重点实验室兰州 730000

收稿日期:2023-12-18 修回日期:2023-12-21 发布日期:2024-01-05
基金资助:
国家重点研发计划(2023YFA1506404); 甘肃省科技计划(23ZDFA003); 甘肃省科技计划(23JRRA1144); 甘肃省科技计划(23JRRA1028); 甘肃省科技计划(23CXGA0043); 兰州市科技计划(2023-1-17); 兰州市科技计划(2023-QN-18); 中央高校基本科研业务专项(lzujbky-2022-ct03); 中央高校基本科研业务专项(lzujbky-2022-sp09); 中央高校基本科研业务专项(lzujbky-2023-ct02); 中央高校基本科研业务专项(lzujbky-2023-pd08); 兰州大学陇药协同创新中心和甘肃省药物研发计划(2022GSMPA0010)

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

Dongsen Duan, Yuan Ma, Yubo Liu, Fu Cheng, Daoyong Zhu(), Shaohua Wang()

State Key Laboratory of Applied Organic Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 730000

Received:2023-12-18 Revised:2023-12-21 Published:2024-01-05
Contact: *E-mail: wangshh@lzu.edu.cn; zhudy@lzu.edu.cn
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)

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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.

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Fig. & Tab. 7

References 22

[1]	(a) Sakakura, T.; Choi, J.-C.; Yasuda, H. Chem. Soc. Rev. 2011, 40, 2435. pmid: 27747133
	(b) Liu, Q.; Wu, L.; Jackstell, R.; Beller, M. Nat. Commun. 2015, 6, 5933. pmid: 27747133
	(c) Correa, A.; Martín, R. Angew. Chem., Int. Ed. 2009, 48, 6201. pmid: 27747133
	(d) Tsuji, Y.; Fujihara, T. Chem. Commun. 2012, 48, 9956. pmid: 27747133
	(e) Börjesson, M.; Moragas, T.; Gallego, D.; Martin, R. ACS Catal. 2016, 6, 6739. pmid: 27747133
	(f) Gui, Y.-Y.; Zhou, W.-J.; Ye, J.-H.; Yu, D.-G. ChemSusChem 2017, 10, 1337. pmid: 27747133
	(g) Chen, K.-H.; Li, H.-R.; He, L.-N. Chin. J. Org. Chem. 2020, 40, 2195 (in Chinese). pmid: 27747133
	( 陈凯宏, 李红茹, 何良年, 有机化学, 2020, 40, 2195.) doi: 10.6023/cjoc202004030 pmid: 27747133
	(h) Guo, X.; Wang, Y.-Z.; Chen, J.; Li, G.-Q.; Xia, J.-B. Chin. J. Org. Chem. 2020, 40, 2208 (in Chinese). pmid: 27747133
	( 郭霄, 王亚洲, 陈洁, 李公强, 夏纪宝, 有机化学, 2020, 40, 2208.) doi: 10.6023/cjoc202002032 pmid: 27747133
	(i) Ye, J.-H.; Ju, Tao.; Huang, H.; Liao, L.-L.; Yu, D.-G. Acc. Chem. Res. 2021, 54, 2518. pmid: 27747133
	(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). pmid: 27747133
	( 窦谦, 汪太民, 李嗣锋, 房丽晶, 翟宏斌, 程斌, 有机化学, 2022, 42, 4257.) doi: 10.6023/cjoc202206003 pmid: 27747133
	(k) Wu, Z.-Q.; Fan, Z.-N.; Xi, C.-J. Chin. Sci. Bull. 2021, 66, 773. pmid: 27747133
[2]	(a) Han, İ. M.; Küçükgüzel, G. Ş. Mini-Rev. Med. Chem. 2020, 20, 1300.
	(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. pmid: 26991022
	(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. pmid: 26991022
	(c) Yang, D.-T.; Zhu, M.; Schiffer, Z. J.; Williams, K.; Song, X.; Liu, X.; Manthiram, K. ACS Catal. 2019, 9, 4699. pmid: 26991022
	(d) Correa, A.; León, T.; Martin, R. J. Am. Chem. Soc. 2014, 136, 1062. pmid: 26991022
	(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. pmid: 26991022
	(f) Grigg, R. D.; Rigoli, J. W.; Van Hoveln, R.; Neale, S.; Schomaker, J. M. Chem.-Eur. J. 2012, 18, 9391. pmid: 26991022
	(g) Moragas, T.; Gaydou, M.; Martin, R. Angew. Chem., Int. Ed. 2016, 55, 5053. doi: 10.1002/anie.201600697 pmid: 26991022
	(h) Wang, L.; Li, T.; Perveen, S.; Zhang, S.; Wang, X.; Ouyang, Y.; Li, P. Angew. Chem., Int. Ed. 2022, 61, e202213943. pmid: 26991022
	(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. pmid: 26991022
	(j) Chen, B.-L.; Zhu, H.-W.; Xiao, Y.; Sun, Q.-L.; Wang, H.; Lu, J.-X. Electrochem. Commun. 2014, 42, 55. pmid: 26991022
	(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. doi: 10.1016/S1872-2067(21)63859-7 pmid: 26991022
	(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. pmid: 26991022
[4]	(a) Meng, Q.-Y.; Schirmer, T. E.; Berger, A. L.; Donabauer, K.; König, B. J. Am. Chem. Soc. 2019, 141, 11393. pmid: 31775498
	(b) Ishida, N.; Masuda, Y.; Imamura, Y.; Yamazaki, K.; Murakami, M. J. Am. Chem. Soc. 2019, 141, 19611. doi: 10.1021/jacs.9b12529 pmid: 31775498
	(c) Lee, H.-J.; Kim, H.; Kim, D.-P. Chem.-Eur. J. 2019, 25, 11641. pmid: 31775498
	(d) Faigl, F.; Schlosser, M. Tetrahedron Lett. 1991, 32, 3369. pmid: 31775498
[5]	(a) Jin, Y.; Caner, J.; Nishikawa, S.; Toriumi, N.; Iwasawa, N. Nat. Commun. 2022, 13, 7584. pmid: 22779807
	(b) Shao, P.; Wang, S.; Chen, C.; Xi, C. Org. Lett. 2016, 18, 2050. pmid: 22779807
	(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. doi: 10.1021/acsomega.1c04943 pmid: 22779807
	(d) Saini, S.; Singh, H.; Prajapati, P. K.; Sinha, A. K.; Jain, S. L. ACS Sustainable Chem. Eng. 2019, 7, 11313. pmid: 22779807
	(e) Greenhalgh, M. D.; Thomas, S. P. J. Am. Chem. Soc. 2012, 134, 11900. doi: 10.1021/ja3045053 pmid: 22779807
	(f) Williams, C. M.; Johnson, J. B.; Rovis, T. J. Am. Chem. Soc. 2008, 130, 14936. pmid: 22779807
	(g) Gaydou, M.; Moragas, T.; Juliá-Hernández, F.; Martin, R. J. Am. Chem. Soc. 2017, 139, 12161. pmid: 22779807
	(h) Meng, Q.-Y.; Wang, S.; Huff, G. S.; König, B. J. Am. Chem. Soc. 2018, 140, 3198. pmid: 22779807
	(i) Greenhalgh, M. D.; Kolodziej, A.; Sinclair, F.; Thomas, S. P. Organometallics 2014, 33, 5811. pmid: 22779807
	(j) Kawashima, S.; Aikawa, K.; Mikami, K. Eur. J. Org. Chem. 2016, 2016, 3166. pmid: 22779807
	(k) Murata, K.; Numasawa, N.; Shimomaki, K.; Takaya, J.; Iwasawa, N. Chem. Commun. 2017, 53, 3098. pmid: 22779807
[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. pmid: 33561344
	(b) Fu, Q.; Bo, Z.-Y.; Ye, J.-H.; Ju, T.; Huang, H.; Liao, L.-L.; Yu, D.-G. Nat. Commun. 2019, 10, 3592. pmid: 33561344
	(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. pmid: 33561344
	(d) Senboku, H.; Komatsu, H.; Fujimura, Y.; Tokuda, M. Synlett 2001, 2001, 0418. pmid: 33561344
	(e) Knowlden, S. W.; Popp, B. V. Organometallics 2022, 41, 1883. pmid: 33561344
	(f) Zhou, C.; Li, M.; Sun, J.; Cheng, J.; Sun, S. Org. Lett. 2021, 23, 2895. pmid: 33561344
	(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. pmid: 33561344
	(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. pmid: 33561344
	(i) Wang, H.; Gao, Y.; Zhou, C.; Li, G. J. Am. Chem. Soc. 2020, 142, 8122. doi: 10.1021/jacs.0c03144 pmid: 33561344
	(j) Zhang, W.; Lin, S. J. Am. Chem. Soc. 2020, 142, 20661. doi: 10.1021/jacs.0c08532 pmid: 33561344
	(k) Benedetti Vega, K.; Campos Delgado, J. A.; Pugnal, L. V. B. L.; König, B.; Menezes Correia, J. T.; Weber Paixão, M. Chem.-Eur. J. 2023, 29, e202203625. pmid: 33561344
	(l) Yatham, V. R.; Shen, Y.; Martin, R. Angew. Chem., Int. Ed. 2017, 56, 10915. pmid: 33561344
	(m) Tortajada, A.; Juliá-Hernández, F.; Börjesson, M.; Moragas, T.; Martin, R. Angew. Chem., Int. Ed. 2018, 57, 15948. doi: 10.1002/anie.201803186 pmid: 33561344
	(n) Wang, H.; Lin, M.-Y.; Fang, H.-J.; Chen, T.-T.; Lu, J.-X. Chin. J. Chem. 2007, 25, 913. pmid: 33561344
	(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. doi: 10.1002/cctc.201901197 pmid: 33561344
	(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. pmid: 33561344
	(q) Shao, P.; Wang, S.; Chen, C.; Xi, C. Chem. Commun. 2015, 51, 6640. pmid: 33561344
	(r) Dérien, S.; Clinet, J.-C.; Duñach, E.; Périchon, J. Tetrahedron 1992, 48, 5235. pmid: 33561344
	(s) Hou, J.; Ee, A.; Cao, H.; Ong, H.-W.; Xu, J.-H.; Wu, J. Angew. Chem., Int. Ed. 2018, 57, 17220. pmid: 33561344
	(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. doi: 10.1021/jacs.0c11896 pmid: 33561344
[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.
	(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.
	(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. doi: 10.1021/jacs.8b08792 pmid: 30518213
[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. doi: 10.1039/c9sc02467k pmid: 32055361
[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.

Entry	Photocatalyst	Amine	Solvent	Time/h	Yield^b/%
1	4DPAIPN	DIPEA	DMSO	6	58
2	4DPAIPN	TEA	DMSO	6	N.D.
3	4DPAIPN	Cy₂NMe	DMSO	6	73
4	4DPAIPN	NIMBA	DMSO	6	75
5^c	4DPAIPN	NIMBA	DMSO	6	30
6^d	4DPAIPN	NIMBA	DMSO	6	65
7	4DPAIPN	NIMBA	DMF	6	69
8	4DPAIPN	NIMBA	NMP	6	45
9	4DPAIPN	NIMBA	MeCN	6	52
10	4CzIPN	NIMBA	DMSO	6	N.D.
11	3DPAFIPN	NIMBA	DMSO	6	70
12	fac-Ir(ppy)₃	NIMBA	DMSO	6	N.D.
13	4DPAIPN	NIMBA	DMSO	1	58
14	4DPAIPN	NIMBA	DMSO	3	70
15	4DPAIPN	NIMBA	DMSO	12	75
16	4DPAIPN	NIMBA	DMSO	24	86 (78)^e

Entry	Photocatalyst	Amine	Solvent	Time/h	Yield^b/%
1	4DPAIPN	DIPEA	DMSO	6	58
2	4DPAIPN	TEA	DMSO	6	N.D.
3	4DPAIPN	Cy₂NMe	DMSO	6	73
4	4DPAIPN	NIMBA	DMSO	6	75
5^c	4DPAIPN	NIMBA	DMSO	6	30
6^d	4DPAIPN	NIMBA	DMSO	6	65
7	4DPAIPN	NIMBA	DMF	6	69
8	4DPAIPN	NIMBA	NMP	6	45
9	4DPAIPN	NIMBA	MeCN	6	52
10	4CzIPN	NIMBA	DMSO	6	N.D.
11	3DPAFIPN	NIMBA	DMSO	6	70
12	fac-Ir(ppy)₃	NIMBA	DMSO	6	N.D.
13	4DPAIPN	NIMBA	DMSO	1	58
14	4DPAIPN	NIMBA	DMSO	3	70
15	4DPAIPN	NIMBA	DMSO	12	75
16	4DPAIPN	NIMBA	DMSO	24	86 (78)^e

可见光诱导的二氧化碳对活化烯烃的脱碳羧基化反应

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

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