Recent Advances on the Carboxylations of C(sp³)–H Bonds Using CO₂ as the Carbon Source

Dedicated to Prof. Masahiro Murakami for his unparalleled contributions on the topic of CO₂ utilization in organic synthesis.

Abstract

Carbon dioxide (CO₂) is widely known as being a sustainable C1 synthon for the synthesis of various carboxylic acid derivatives, including essential natural and unnatural amino acids. While it is sustainable, the high thermodynamic stability and kinetic inertness of the CO₂ molecule is a major drawback to its wider use in organic synthesis. However, the reduction of this inert and highly stable CO₂ molecule has been carried out successfully over the past few years using various stoichiometric as well as catalytic approaches. Initially, chemists employed transition-metal/transition-metal-free thermochemical methods for the incorporation of CO₂ into organic compounds, however, gradually, the introduction of greener approaches such as visible-light-induced photoredox catalysis and electrocatalysis became revolutionary for the synthesis of carboxylic acids under mild reaction conditions. In this short review, we discuss the recent advances in carboxylation reactions via functionalization of the (sp³)C–H bonds of various organic molecules with CO₂ using thermochemical, photochemical and electrochemical methods.

1 Introduction

2 Transition-Metal/Transition-Metal-Free Thermochemical Carbox ylations of C(sp³)–H Bonds

2.1 C(sp³)–H Bond Carboxylation of Carbonyls

2.2 Allylic, Benzylic and Alkyl C(sp³)–H Bond Carboxylation

3 Photochemical C(sp³)–H Bond Carboxylation

3.1 Allylic C(sp³)–H Bond Carboxylation

3.2 Benzylic C(sp³)–H Bond Carboxylation

4 Electrochemical Carboxylation of C(sp³)–H Bonds

5 Conclusion and Outlook

Key words

carbon dioxide - transition-metal - transition-metal-free - thermochemical strategy - visible-light-induced photocatalysis - electrocatalysis - reductive C–H carboxylations - carboxylic acids

Publikationsverlauf

Eingereicht: 15. Dezember 2022

Angenommen nach Revision: 13. Januar 2023

Accepted Manuscript online:
13. Januar 2023

Artikel online veröffentlicht:
16. Februar 2023

• References

• 1 Maag H. Prodrugs of Carboxylic Acids . In Prodrugs: Challenges and Rewards, Vol. V. Stella VJ, Borchardt RT, Hageman MJ, Oliyai R, Maag H, Tilley JW. Biotechnology; Pharmaceutical Aspects; Springer: New York: 2007: 703
• 2a Modern Carbonylation Methods . Kollar L. Wiley-VCH; Weinheim: 2008
• 2b Limburg B, Maquilón C, Kleij AW. Photochemical and Substrate-Driven CO₂ Conversion. In CO₂ as a Building Block in Organic Synthesis. Das S. Wiley-VCH; Weinheim: 2020
• 3a Sakakura T, Choi J.-C, Yasuda H. Chem. Rev. 2007; 107: 2365
• 3b Huang K, Sun C.-L, Shi Z.-J. Chem. Soc. Rev. 2011; 40: 2435
• 3c He M, Sun Y, Han B. Angew. Chem. Int. Ed. 2013; 52: 9620
• 3d Martín C, Fiorani G, Kleij AW. ACS Catal. 2015; 5: 1353
• 3e Sekine K, Yamada T. Chem. Soc. Rev. 2016; 45: 4524
• 3f Bobbink FD, Gruszka W, Hulla M, Das S, Dyson PJ. Chem. Commun. 2016; 52: 10787
• 3g Hirapara P, Riemer D, Hazra N, Gajera J, Finger M, Das S. Green Chem. 2017; 19: 5356
• 3h Luo J, Larrosa I. ChemSusChem 2017; 10: 3317
• 3i Song Q.-W, Zhou Z.-H, He L.-N. Green Chem. 2017; 19: 3707
• 3j Riemer D, Mandaviya B, Schilling W, Götz AC, Kühl T, Finger M, Das S. ACS Catal. 2018; 8: 3030
• 3k Schilling W, Das S. Tetrahedron Lett. 2018; 59: 3821
• 3l Riemer D, Schilling W, Götz AG, Zhang Y, Gehrke S, Tkach I, Hollóczki O, Das S. ACS Catal. 2018; 8: 11679
• 3m Burkart MD, Hazari N, Tway CL, Zeitler EL. ACS Catal. 2019; 9: 7937
• 3n Wang S, Xi C. Chem. Soc. Rev. 2019; 48: 382
• 3o Yang Y, Lee J.-W. Chem. Sci. 2019; 10: 3905
• 3p Zhang L, Li Z, Takimoto M, Hou Z. Chem. Rec. 2020; 20: 494
• 3q Song L, Jiang Y.-X, Zhang Z, Gui Y.-Y, Zhou X.-Y, Yu D.-G. Chem. Commun. 2020; 56: 8355
• 3r Liu Q, Wu L, Jackstell R, Beller M. Nat. Commun. 2015; 6: 5933
• 3s Fujihara T, Tsuji Y. Front. Chem. 2019; 7: 430
• 4a Correa A, Martin R. Angew. Chem. Int. Ed. 2009; 48: 6201
• 4b Ackermann L. Angew. Chem. Int. Ed. 2011; 50: 3842
• 4c Boogaerts II, Nolan SP. Chem. Commun. 2011; 47: 3021
• 5a Julia-Hernandez F, Gaydou M, Serrano E, van Gemmeren M, Martin R. Top Curr. Chem. 2016; 374: 45
• 5b Borjesson M, Moragas T, Gallego D, Martin R. ACS Catal. 2016; 6: 6739
• 5c Mei T.-S, Chen Y.-G, Xu X.-T, Zhang K, Li Y.-Q, Zhang L.-P, Fang P. Synthesis 2018; 50: 35
• 5d Yan S.-S, Fu Q, Liao L.-L, Sun G.-Q, Ye J.-H, Gong L, Bo-Xue Y.-Z, Yu D.-G. Coord. Chem. Rev. 2018; 374: 439
• 5e Zhang Y, Zhang T, Das S. Green Chem. 2020; 22: 1800
• 5f Schilling W, Das S. ChemSusChem 2020; 13: 6246
• 5g Cauwenbergh R, Das S. Green Chem. 2021; 23: 2553
• 5h Cauwenbergh R, Goyal V, Maiti R, Natte K, Das S. Chem. Soc. Rev. 2022; 51: 9371
• 6a Schneider J, Jia H, Muckerman JT, Fujita E. Chem. Soc. Rev. 2012; 41: 2036
• 6b Li YN, Ma R, He L.-N, Diao Z.-F. Catal. Sci. Technol. 2014; 4: 1498

Selected reviews on transition-metal-catalyzed CO₂ incorporation:
• 7a Cokoja M, Bruckmeier C, Rieger B, Herrmann WA, Kühn FE. Angew. Chem. Int. Ed. 2011; 50: 8510
• 7b Tsuji Y, Fujihara T. Chem. Commun. 2012; 48: 9956
• 7c Zhang L, Hou Z. Chem. Sci. 2013; 4: 3395
• 7d Song J, Liu Q, Liu H, Jiang X. Eur. J. Org. Chem. 2018; 696
• 7e Sang R, Hu Y, Razzaq R, Mollaert G, Atia H, Bentrup U, Sharif M, Neumann H, Junge H, Jackstell R, Maes BU. W, Beller M. Nat. Commun. 2022; 13: 4432
• 7f Wei D, Sang R, Sponholz P, Junge H, Beller M. Nat. Energy 2022; 7: 438
• 7g Marx M, Frauendorf H, Spannenberg A, Neumann H, Beller M. JACS Au 2022; 2: 731
• 7h Qiao C, Shi W, Brandolese A, Benet-Buchholz J, Escudero-Adán E, Kleij AW. Angew. Chem. Int. Ed. 2022; 61: e2022050

For selected reviews and reports on photoredox catalysis, see:
• 8a Fagnoni M, Dondi D, Ravelli D, Albini A. Chem. Rev. 2007; 107: 2725
• 8b Hoffmann N. J. Photochem. Photobiol., C 2008; 9: 43
• 8c Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102
• 8d Tucker JW, Stephenson CR. J. J. Org. Chem. 2012; 77: 1617
• 8e Ischay MA, Yoon TP. Eur. J. Org. Chem. 2012; 3359
• 8f Xuan J, Xiao W.-J. Angew. Chem. Int. Ed. 2012; 51: 6828
• 8g Xi Y, Yi H, Lei A. Org. Biomol. Chem. 2013; 11: 2387
• 8h Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
• 8i Reckenthaler M, Griesbeck AG. Adv. Synth. Catal. 2013; 355: 2727
• 8j Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075 ; and references cited therein
• 8k Marzo L, Pagire SK, Reiser O, König B. Angew. Chem. Int. Ed. 2018; 57: 10034
• 8l Kollmann J, Yu Z, Schilling W, Tong Z, Riemer D, Das S. Green Chem. 2019; 21: 1916
• 8m Zhang Y, Schilling W, Riemer D, Das S. Nat. Protoc. 2020; 15: 822
• 8n Cauwenbergh R, Das S. Synlett 2021; 32: 129
• 8o Vanderghinste J, Das S. Synthesis 2022; 54: 3383
• 8p Zhang Y, Sahoo PK, Ren P, Qin Y, Cauwenbergh R, Nimmegeers P, SivaRaman G, Passel SV, Guidetti A, Das S. Chem. Commun. 2022; 58: 11454
• 9a Ritter SK. Chem. Eng. News 2017; 95: 23
• 9b Ritter S. Chem. Eng. News 2017; 95: 21
• 9c Perry SC, Pangotra D, Vieira L, Csepei L.-I, Sieber V, Wang L, Ponce de León C, Walsh FC. Nat. Chem. Rev. 2019; 3: 442
• 9d Kim C.-C, Kim Y, Jeong S.-H, Oh KH, Nam KT, Sun J.-Y. ACS Nano 2020; 14: 11743
• 9e Davey SG. Nat. Chem. Rev. 2021; 5: 837
• 9f Leech MC, Lam K. Nat. Chem. Rev. 2022; 6: 275
• 9g Li J, Zhang Y, Kuruvinashetti K, Kornienko N. Nat. Chem. Rev. 2022; 6: 303
• 9h For a comparison between photo and electrocatalysis, see: Tay NE. S, Lehnherr D, Rovis T. Chem. Rev. 2022; 122: 2487
• 10a Gutekunst WR, Baran PS. Chem. Soc. Rev. 2011; 40: 1976
• 10b Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
• 10c Davies HM. L, Morton D. J. Org. Chem. 2016; 81: 343
• 10d Wan JP, Gan L, Liu Y. Org. Biomol. Chem. 2017; 15: 9031
• 11a Newhouse T, Baran PS. Angew. Chem. Int. Ed. 2011; 50: 3362
• 11b McMurray L, O’Hara F, Gaunt MJ. Chem. Soc. Rev. 2011; 40: 1885
• 11c Brueckl T, Baxter RD, Ishihara Y, Baran PS. Acc. Chem. Res. 2012; 45: 826
• 12a https://climate.nasa.gov/vital-signs/carbon-dioxide (accessed Feb 01, 2023)
• 12b Marland G, Boden TA, Andres RJ. Global, Regional, and National Fossil-Fuel CO₂ Emissions . In Trends; A Compendium of Data on Global Change; Carbon Dioxide Information Analysis Center, Oak Ridge National Laboratory: 2008. https://cdiac.ess-dive.lbl.gov/trends/emis/overview.html (accessed Feb 01, 2023)
• 12c Etheridge DM, Steele LP, Langenfelds RL, Francey RJ, Barnola J.-M, Morgan VI. Historical CO₂ Records form the Law Dome DE08, DE08-2, and DSS Ice Cores . In Trends: A Compendium of Data on Global Change . Carbon Dioxide Information Analysis Center, Oak Ridge National Laboratory, U.S. Department of Energy; Oak Ridge: 1998. https://cdiac.ess-dive.lbl.gov/trends/co2/lawdome.html (accessed Feb 01, 2023)
• 13a Riduan SN, Zhang Y. Dalton Trans. 2010; 39: 3347
• 13b Martín R, Kleij AW. ChemSusChem 2011; 4: 1259
• 13c Gui Y.-Y, Zhou W.-J, Ye J.-H, Yu D.-G. ChemSusChem 2017; 10: 1337
• 13d Li Y, Cui X, Dong K, Junge K, Beller M. ACS Catal. 2017; 7: 1077
• 13e Tortajada A, Julia-Hernandez F, Borjesson M, Moragas T, Martin R. Angew. Chem. Int. Ed. 2018; 57: 15948
• 14 Hong J, Li M, Zhang J, Sun B, Mo F. ChemSusChem 2019; 12: 6

For selected reports on photocatalytic CO₂ incorporation, see:
• 15a Toki S, Hida S, Takamuku S, Sakurai H. Nippon Kagaku Kaishi 1984; 1: 152
• 15b Berton M, Mello R, Núñez ME. G. ChemSusChem 2016; 9: 3397
• 15c Seo H, Liu A, Jamison TF. J. Am. Chem. Soc. 2017; 139: 13969
• 15d Meng Q.-Y, Wang S, König B. Angew. Chem. Int. Ed. 2017; 56: 13426
• 15e Meng QY, Wang S, Huff GS, Konig B. J. Am. Chem. Soc. 2018; 140: 3198
• 15f Berton M, Mello R, Acerete R, Núñez ME. G. J. Org. Chem. 2018; 83: 96
• 15g Mello R, Arango-Daza JC, Varea T, Núñez ME. G. J. Org. Chem. 2018; 83: 13381

Selected reviews on visible-light-triggered photocatalytic CO₂ incorporation:
• 15h Hou J, Li J.-S, Wu J. Asian J. Org. Chem. 2018; 7: 1439
• 15i Tan F, Yin G. Chin. J. Chem. 2018; 36: 545
• 15j Yeung CS. Angew. Chem. Int. Ed. 2019; 58: 5492
• 15k 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
• 15l Pradhan S, Roy S, Sahoo B, Chatterjee I. Chem. Eur. J. 2021; 27: 2254

Selected reviews and reports on electrocatalytic CO₂ incorporation:
• 16a Finn C, Schnittger S, Yellowlees LJ, Love JB. Chem. Commun. 2012; 48: 1392
• 16b Matthessen R, Fransaer J, Binnemans K. Beilstein J. Org. Chem. 2014; 10: 2484
• 16c Fenner S, Ackermann L. Green Chem. 2016; 18: 3804
• 16d Senboku H, Katayama A. Curr. Opin. Green Sustainable Chem. 2017; 3: 50
• 16e Cao Y, He X, Wang N, Li H.-R, He L.-N. Chin. J. Chem. 2018; 36: 644
• 16f Zhang S, Fan Q, Xia R, Meyer TJ. Acc. Chem. Res. 2020; 53: 255
• 16g Ang NW. J, Oliveira JC. A, Ackermann L. Angew. Chem. Int. Ed. 2020; 59: 12842
• 16h Alkayal A, Tabas V, Montanaro S, Wright IA, Malkov AV, Buckley BR. J. Am. Chem. Soc. 2020; 142: 1780
• 16i Sheta AM, Mashaly MA, Said SB, Elmorsy SS, Malkov AV, Buckley BR. Chem. Sci. 2020; 11: 9109
• 16j Sheta AM, Alkayal A, Mashaly MA, Said SB, Elmorsy SS, Malkov AV, Buckley BR. Angew. Chem. Int. Ed. 2021; 60: 21832
• 16k You Y, Kanna W, Takano H, Hayashi H, Maeda S, Mita T. J. Am. Chem. Soc. 2022; 144: 3685
• 16l Liao L.-L, Wang Z, Cao K, Sun G, Zhang W, Ran C, Li Y, Chen L, Cao G, Yu D. J. Am. Chem. Soc. 2022; 144: 2062
• 16m Nandi S, Jana R. Asian J. Org. Chem. 2022; 11: e202200356
• 17a Morgenstern DA, Wittrig RE, Fanwick PE, Kubiak CP. J. Am. Chem. Soc. 1993; 115: 6470
• 17b Otero MD, Batanero B, Barba F. Tetrahedron Lett. 2006; 47: 2171
• 17c Chmiel AF, Williams OP, Chernowsky CP, Yeung CS, Wickens ZK. J. Am. Chem. Soc. 2021; 143: 10882
• 17d Alektiar SN, Wickens ZK. J. Am. Chem. Soc. 2021; 143: 13022
• 17e Song L, Wang W, Yue J.-P, Jiang Y.-X, Wei M.-K, Zhang H.-P, Yan S.-S, Liao L.-L, Yu D.-G. Nat. Catal. 2022; 5: 832
• 18 Qin W, Subhani M, Jiang C, Lu H. Org. Biomol. Chem. 2021; 19: 10030
• 19a Re PD, Sandri E. Chem. Ber. 1960; 93: 1085
• 19b Zhang W.-Z, Yang M.-W, Yang X.-T, Shi L.-L, Wang H.-B, Lu X.-B. Org. Chem. Front. 2016; 3: 217
• 20 Kikuchi S, Sekine K, Ishida T, Yamada T. Angew. Chem. Int. Ed. 2012; 51: 6989
• 21 Sekine K, Takayanagi A, Kikuchi S, Yamada T. Chem. Commun. 2013; 49: 11320
• 22 Zhang W.-Z, Shi L.-L, Liu C, Yang X.-T, Wang Y.-B, Luo Y, Lu X.-B. Org. Chem. Front. 2014; 1: 275
• 23 Sadamitsu Y, Komatsuki K, Saito K, Yamada T. Org. Lett. 2017; 19: 3191
• 24 Bernier D, Brückner R. Synthesis 2007; 2249
• 25 Zhou M, Yoshida Y, Ishii S, Noguchi H. Synth. Commun. 1999; 29: 2241
• 26 Zhang W.-Z, Yang M.-W, Lu X.-B. Green Chem. 2016; 18: 4181
• 27a Afarinkia K, Vinader V, Nelson TD, Posner GH. Tetrahedron 1992; 48: 9111
• 27b Kim ES, Kim KH, Kim SH, Kim JN. Tetrahedron Lett. 2009; 50: 5098
• 27c Frébault F, Luparia M, Oliveira MT, Goddard R, Maulide N. Angew. Chem. Int. Ed. 2010; 49: 5672
• 27d Sun C.-L, Fürstner A. Angew. Chem. Int. Ed. 2013; 52: 13071
• 28 Mita T, Michigami K, Sato Y. Org. Lett. 2012; 14: 3462
• 29 Mita T, Michigami K, Sato Y. Chem. Asian J. 2013; 8: 2970
• 30 Michigami K, Mita T, Sato Y. J. Am. Chem. Soc. 2017; 139: 6094
• 31a Bartholomäus R, Bachmann J, Mang C, Haustedt LO, Harms K, Koert U. Eur. J. Org. Chem. 2013; 180
• 31b Jiang X, Wang M, Song S, Xu Y, Miao Z, Zhang A. RSC Adv. 2015; 5: 27502
• 32 Ueno A, Takimoto M, Hou Z. Org. Biomol. Chem. 2017; 15: 2370
• 33a Terao J, Kambe N. Acc. Chem. Res. 2008; 41: 1545
• 33b Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011; 111: 1417
• 34 Juliá-Hernández F, Moragas T, Cornella J, Martin R. Nature 2014; 545: 84
• 35a Wolff ME. Chem. Rev. 1963; 63: 55
• 35b Breslow R, Heyer D. J. Am. Chem. Soc. 1982; 104: 2045
• 36 Ishida N, Masuda Y, Uemoto S, Murakami M. Chem. Eur. J. 2016; 22: 6524
• 37 Masuda Y, Ishida N, Murakami M. J. Am. Chem. Soc. 2015; 137: 14063
• 38 Seo H, Katcher MH, Jamison TF. Nat. Chem. 2017; 9: 453
• 39 Ishida N, Masuda Y, Imamura Y, Yamazaki K, Murakami M. J. Am. Chem. Soc. 2019; 141: 19611
• 40 Meng Q.-Y, Schirmer TE, Berger AL, Donabauer K, König B. J. Am. Chem. Soc. 2019; 141: 11393
• 41 Kambe N, Iwasaki T, Terao J. Chem. Soc. Rev. 2011; 40: 4937
• 42 Sahoo B, Bellotti P, Julia-Hernandez F, Meng QY, Crespi S, König B, Martin R. Chem. Eur. J. 2019; 25: 9001
• 43 Song L, Fu D.-M, Chen L, Jiang Y.-X, Ye J.-H, Zhu L, Lan Y, Fu Q, Yu D.-G. Angew. Chem. Int. Ed. 2020; 59: 21121
• 44 Senboku H, Yamauchi Y, Fukuhara T, Hara S. Electrochemistry 2006; 74: 612
• 45 Muchez L, De Vos DE, Kim M. ACS Sustainable Chem. Eng. 2019; 7: 15860
• 46 Ran C.-K, Chen X.-W, Gui Y.-Y, Liu J, Song L, Ren K, Yu D.-G. Sci. China Chem. 2020; 63: 1336