Carboxylation of Alkenes with CO2 via Photocatalytic Cleavage of C=C Double Bonds

Pan-Feng Yuan; Qing-Yuan Meng

doi:10.1055/s-0043-1763755

Synlett, Table of Contents

Synlett 2024; 35(17): 1937-1946
DOI: 10.1055/s-0043-1763755

synpacts

Carboxylation of Alkenes with CO₂ via Photocatalytic Cleavage of C=C Double Bonds

Pan-Feng Yuan

^aBeijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, No. 2, 1^st North Street, Zhongguancun, Haidian District, Beijing 100190, P. R. of China

,

Qing-Yuan Meng ∗

^aBeijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, No. 2, 1^st North Street, Zhongguancun, Haidian District, Beijing 100190, P. R. of China

^bUniversity of Chinese Academy of Sciences, No. 80 Zhongguancun East Road, Haidian District, Beijing 100049, P. R. of China

› Author Affiliations

Abstract

All articles of this category

Abstract

The cleavage of double bonds in alkenes constitutes an integral process in converting feedstock materials into high-value synthetic intermediates. Well-known examples such as the oxidative cleavage of olefins and olefin metathesis only facilitate the synthesis of oxygen-containing compounds and the recombination of olefins. Therefore, it is appealing to extend C=C double bond cleavage to yield more abundant transformations. Herein, we report a novel photocatalytic approach for the deconstructive carboxylation of alkenes with CO₂ for the synthesis of carboxylic acids in the absence of transition metals. Compared with reported carboxylations with CO₂ during which carbon numbers are typically increased, we achieve the exchange of carbon dioxide with one of the carbons of the alkene double bond, thus providing carboxylic acids with unchanged carbon numbers when terminal alkenes are used.

Key words

alkenes - carbon dioxide - carboxylation - photocatalysis - synthetic methods

Full Text

References

References

1a Braunstein P, Matt D, Nobel D. Chem. Rev. 1988; 88: 747
1b Sakakura T, Choi J.-C, Yasuda H. Chem. Rev. 2007; 107: 2365
1c Tortajada A, Juliá-Hernández F, Börjesson M, Moragas T, Martin R. Angew. Chem. Int. Ed. 2018; 57: 15948
1d Song L, Jiang Y.-X, Zhang Z, Gui Y.-Y, Zhou X.-Y, Yu D.-G. Chem. Commun. 2020; 56: 8355

2 Prodrugs: Challenges and Rewards, Part 1. Stella V, Borchardt R, Hageman M, Oliyai R, Maag H, Tilley J. Springer; New York: 2007
3 Aresta M, Dibenedetto A, Quaranta E. Reaction Mechanisms in Carbon Dioxide Conversion . Springer-Verlag; Berlin/Heidelberg: 2016

4a Huang K, Sun C.-L, Shi Z.-J. Chem. Soc. Rev. 2011; 40: 2435
4b Börjesson M, Moragas T, Gallego D, Martin R. ACS Catal. 2016; 6: 6739
4c Chen Y.-G, Xu X.-T, Zhang K, Li Y.-Q, Zhang L.-P, Fang P, Mei T.-S. Synthesis 2018; 50: 35
4d Tortajada A, Börjesson M, Martin R. Acc. Chem. Res. 2021; 54: 3941

5a Folest J.-C, Duprilot J.-M, Perichon J, Robin Y, Devynck J. Tetrahedron Lett. 1985; 26: 2633
5b Amatore C, Jutand A. J. Am. Chem. Soc. 1991; 113: 2819
5c Fujihara T, Nogi K, Xu T, Terao J, Tsuji Y. J. Am. Chem. Soc. 2012; 134: 9106
5d León T, Correa A, Martin R. J. Am. Chem. Soc. 2013; 135: 1221
5e Chen B.-L, Zhu H.-W, Xiao Y, Sun Q.-L, Wang H, Lu J.-X. Electrochem. Commun. 2014; 42: 55
5f Zhang S, Chen W.-Q, Yu A, He L.-N. ChemCatChem 2015; 7: 3972
5g Wang Y, Jiang X, Wang B. Chem. Commun. 2020; 56: 14416

6a Correa A, Martín R. J. Am. Chem. Soc. 2009; 131: 15974
6b Hang W, Yi Y, Xi C. Adv. Synth. Catal. 2020; 362: 2337
6c Davies J, Lyonnet JR, Carvalho B, Sahoo B, Day CS, Juliá-Hernández F, Duan Y, Álvaro V.-R, Obst M, Norrby P.-O, Hopmann KH, Martin R. J. Am. Chem. Soc. 2024; 146: 1753

7a Ebert GW, Juda WL, Kosakowski RH, Ma B, Dong L, Cummings KE, Phelps MV. B, Mostafa AE, Luo J. J. Org. Chem. 2005; 70: 4314
7b Tran-Vu H, Daugulis O. ACS Catal. 2013; 3: 2417

8a Correa A, León T, Martin R. J. Am. Chem. Soc. 2014; 136: 1062
8b Moragas T, Cornella J, Martin R. J. Am. Chem. Soc. 2014; 136: 17702
8c Mita T, Higuchi Y, Sato Y. Chem. Eur. J. 2015; 21: 16391

9a Sun S, Yu J.-T, Jiang Y, Cheng J. Adv. Synth. Catal. 2015; 357: 2022
9b Yanagi T, Somerville RJ, Nogi K, Martin R, Yorimitsu H. ACS Catal. 2020; 10: 2117
9c Yorimitsu H. Chem. Rec. 2021; 21: 3356
9d Tang S, Zhao X, Yang L, Li B, Wang B. Angew. Chem. Int. Ed. 2022; 61: e202212975

10 Moragas T, Gaydou M, Martin R. Angew. Chem. Int. Ed. 2016; 55: 5053
11 Tang S, Liu Z, Zhang J, Li B, Wang B. Angew. Chem. Int. Ed. 2024; 63: e202318572

12a Ukai K, Aoki M, Takaya J, Iwasawa N. J. Am. Chem. Soc. 2006; 128: 8706
12b Ohishi T, Nishiura M, Hou Z. Angew. Chem. Int. Ed. 2008; 47: 5792

13a 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
13b Yang D.-T, Zhu M, Schiffer ZJ, Williams K, Song X, Liu X, Manthiram K. ACS Catal. 2019; 9: 4699
13c 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
13d Bo Z.-Y, Yan S.-S, Gao T.-Y, Song L, Ran C.-K, He Y, Zhang W, Cao G.-M, Yu D.-G. Chin. J. Catal. 2022; 43: 2388
13e 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
13f 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
13g Wang Y, Zhao Z, Pan D, Wang S, Jia K, Ma D, Yang G, Xue X.-S, Qiu Y. Angew. Chem. Int. Ed. 2022; 61: e202210201

14a Masuda Y, Ishida N, Murakami M. J. Am. Chem. Soc. 2015; 137: 14063
14b Seo H, Katcher MH, Jamison TF. Nat. Chem. 2017; 9: 453
14c Ishida N, Masuda Y, Imamura Y, Yamazaki K, Murakami M. J. Am. Chem. Soc. 2019; 141: 19611
14d Meng Q.-Y, Schirmer TE, Berger AL, Donabauer K, König B. J. Am. Chem. Soc. 2019; 141: 11393
14e Schmalzbauer M, Svejstrup TD, Fricke F, Brandt P, Johansson MJ, Bergonzini G, König B. Chem 2020; 6: 2658
14f 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
14g Zhao Z, Liu Y, Wang S, Tang S, Ma D, Zhu Z, Guo C, Qiu Y. Angew. Chem. Int. Ed. 2023; 62: e202214710
14h 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

15 Hong J, Li M, Zhang J, Sun B, Mo F. ChemSusChem 2019; 12: 6

16a Zhang Z, Gong L, Zhou X.-Y, Yan S.-S, Li J, Yu D.-G. Acta Chim. Sin. 2019; 77: 783
16b Bertuzzi G, Cerveri A, Lombardi L, Bandini M. Chin. J. Chem. 2021; 39: 3116

17a Williams CM, Johnson JB, Rovis T. J. Am. Chem. Soc. 2008; 130: 14936
17b Greenhalgh MD, Thomas SP. J. Am. Chem. Soc. 2012; 134: 11900
17c Ostapowicz TG, Schmitz M, Krystof M, Klankermayer J, Leitner W. Angew. Chem. Int. Ed. 2013; 52: 12119
17d Yatham VR, Shen Y, Martin R. Angew. Chem. Int. Ed. 2017; 56: 10915
17e Meng Q.-Y, Wang S, Huff GS, König B. J. Am. Chem. Soc. 2018; 140: 3198
17f 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

18a Fujihara T, Xu T, Semba K, Terao J, Tsuji Y. Angew. Chem. Int. Ed. 2011; 50: 523
18b Li S, Yuan W, Ma S. Angew. Chem. Int. Ed. 2011; 50: 2578
18c Zhang L, Cheng J, Carry B, Hou Z. J. Am. Chem. Soc. 2012; 134: 14314
18d Wang X, Nakajima M, Martin R. J. Am. Chem. Soc. 2015; 137: 8924
18e Hou J, Ee A, Feng W, Xu J.-H, Zhao Y, Wu J. J. Am. Chem. Soc. 2018; 140: 5257

19 Cao G.-M, Hu X.-L, Liao L.-L, Yan S.-S, Song L, Chruma JJ, Gong L, Yu D.-G. Nat. Commun. 2021; 12: 3306

20a Fan X, Gong X, Ma M, Wang R, Walsh PJ. Nat. Commun. 2018; 9: 4936
20b Ju T, Fu Q, Ye J.-H, Zhang Z, Liao L.-L, Yan S.-S, Tian X.-Y, Luo S.-P, Li J, Yu D.-G. Angew. Chem. Int. Ed. 2018; 57: 13897

21a Zhou W.-J, Wang Z.-H, Liao L.-L, Jiang Y.-X, Cao K.-G, Ju T, Li Y, Cao G.-M, Yu D.-G. Nat. Commun. 2020; 11: 3263
21b 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
21c Gao Y, Wang H, Chi Z, Yang L, Zhou C, Li G. CCS Chem. 2022; 4: 1565
21d Yi Y, Fan Z, Xi C. Green Chem. 2022; 24: 7894
21e You Y, Kanna W, Takano H, Hayashi H, Maeda S, Mita T. J. Am. Chem. Soc. 2022; 144: 3685

22a Jiang Y.-X, Chen L, Ran C.-K, Song L, Zhang W, Liao L.-L, Yu D.-G. ChemSusChem 2020; 13: 6312
22b Xiao H.-Z, Yu B, Yan S.-S, Zhang W, Li X.-X, Bao Y, Luo S.-P, Ye J.-H, Yu D.-G. Chin. J. Catal. 2023; 50: 222
22c Liu Y, Wang Z.-H, Xue G.-H, Chen L, Yuan L.-H, Li Y.-W, Yu D.-G, Ye J.-H. Chin. Chem. Lett. 2024; 35: 109138

23 Liao L.-L, Wang Z.-H, Cao K.-G, Sun G.-Q, Zhang W, Ran C.-K, Li Y, Chen L, Cao G.-M, Yu D.-G. J. Am. Chem. Soc. 2022; 144: 2062

24a Baumann H, Bühler M, Fochem H, Hirsinger F, Zoebelein H, Falbe J. Angew. Chem. Int. Ed. 1988; 27: 41
24b Corma A, Iborra S, Velty A. Chem. Rev. 2007; 107: 2411
24c Köckritz A, Blumenstein M, Martin A. Eur. J. Lipid Sci. Technol. 2010; 112: 58

25a Chen F, Wang T, Jiao N. Chem. Rev. 2014; 114: 8613
25b Souillart L, Cramer N. Chem. Rev. 2015; 115: 9410
25c Liang Y.-F, Bilal M, Tang L.-Y, Wang T.-Z, Guan Y.-Q, Cheng Z, Zhu M, Wei J, Jiao N. Chem. Rev. 2023; 123: 12313

26a Buchi G, Ayer DE. J. Am. Chem. Soc. 1956; 78: 689
26b Caron S, Dugger RW, Ruggeri SG, Ragan JA, Ripin DH. B. Chem. Rev. 2006; 106: 2943
26c Van Ornum SG, Champeau RM, Pariza R. Chem. Rev. 2006; 106: 2990
26d Rajagopalan A, Lara M, Kroutil W. Adv. Synth. Catal. 2013; 355: 3321
26e Spannring P, Bruijnincx PC. A, Weckhuysen BM, Klein Gebbink RJ. M. Catal. Sci. Technol. 2014; 4: 2182
26f Cousin T, Chatel G, Kardos N, Andrioletti B, Draye M. Catal. Sci. Technol. 2019; 9: 5256

27a Vougioukalakis GC, Grubbs RH. Chem. Rev. 2010; 110: 1746
27b Wang T, Jiao N. J. Am. Chem. Soc. 2013; 135: 11692

28a Deng Y, Wei X.-J, Wang H, Sun Y, Noël T, Wang X. Angew. Chem. Int. Ed. 2017; 56: 832
28b Urgoitia G, SanMartin R, Herrero MT, Domínguez E. ACS Catal. 2017; 7: 3050

29 Wang H, Toh RW, Shi X, Wang T, Cong X, Wu J. Nat. Commun. 2020; 11: 4462
30 Huang Z, Guan R, Shanmugam M, Bennett EL, Robertson CM, Brookfield A, McInnes EJ. L, Xiao J. J. Am. Chem. Soc. 2021; 143: 10005

31a Ruffoni A, Hampton C, Simonetti M, Leonori D. Nature 2022; 610: 81
31b Wise DE, Gogarnoiu ES, Duke AD, Paolillo JM, Vacala TL, Hussain WA, Parasram M. J. Am. Chem. Soc. 2022; 144: 15437

32 Yuan P.-F, Yang Z, Zhang S.-S, Zhu C.-M, Yang X.-L, Meng Q.-Y. Angew. Chem. Int. Ed. 2024; 63: e202313030
33 Yu X.-Y, Chen J.-R, Xiao W.-J. Chem. Rev. 2021; 121: 506
34 Jiang H, Studer A. Chem. Soc. Rev. 2020; 49: 1790

35a McNally A, Prier CK, MacMillan DW. C. Science 2011; 334: 1114
35b Miyake Y, Nakajima K, Nishibayashi Y. J. Am. Chem. Soc. 2012; 134: 3338
35c Ruiz Espelt L, McPherson IS, Wiensch EM, Yoon TP. J. Am. Chem. Soc. 2015; 137: 2452
35d Zheng S, Chen Z, Hu Y, Xi X, Liao Z, Li W, Yuan W. Angew. Chem. Int. Ed. 2020; 59: 17910

36 Speckmeier E, Fischer TG, Zeitler K. J. Am. Chem. Soc. 2018; 140: 15353
37 Singh PP, Srivastava V. Org. Biomol. Chem. 2021; 19: 313
38 Griller D, Ingold KU. Acc. Chem. Res. 1980; 13: 317

39a Aycock RA, Pratt CJ, Jui NT. ACS Catal. 2018; 8: 9115
39b Leng L, Fu Y, Liu P, Ready JM. J. Am. Chem. Soc. 2020; 142: 11972
39c Shen Y, Funez-Ardoiz I, Schoenebeck F, Rovis T. J. Am. Chem. Soc. 2021; 143: 18952
39d Wu Z, Gockel SN, Hull KL. Nat. Commun. 2021; 12: 5956

40a Hou J, Ee A, Cao H, Ong H.-W, Xu J.-H, Wu J. Angew. Chem. Int. Ed. 2018; 57: 17220
40b Zhang B, Yi Y, Wu Z.-Q, Chen C, Xi C. Green Chem. 2020; 22: 5961
40c Hahm H, Kim J, Ryoo JY, Han MS, Hong S. Org. Biomol. Chem. 2021; 19: 6301