Photoinduced Dearomative Multiple Functionalization of Quinolines to Construct Highly Substituted 3D Frameworks

Abstract

Dearomative functionalization of quinolines expands the chemical diversity of highly functionalized 3D frameworks, such as 1,2,3,4- and 5,6,7,8-tetrahydroquinoline derivatives, which are important pharmacophores, with minimal synthetic costs. In this short review, we cover recent reports on the visible-light-induced dearomative functionalization of quinolines with an emphasis on reaction design/strategies and mechanistic studies and provide a theoretical basis for developing further dearomative syntheses in the future.

1 Introduction

2 Dearomative Functionalizations through the Formation of Photoexcited Quinolines

3 Dearomative Functionalizations through the Formation of Photoexcited Reagents/Intermediates

4 Conclusion

Key words

dearomative functionalization - photoinduced reactions - quinoline - tetrahydroquinoline - 3D frameworks - mechanistic studies - DFT calculations

Publication History

Received: 27 November 2024

Accepted after revision: 30 December 2024

Article published online:
18 February 2025

• References

• 1 Lovering F, Bikker J, Humblet C. J. Med. Chem. 2009; 52: 6752
• 2a Aldeghi M, Malhotra S, Selwood DL, Chan AW. E. Chem. Biol. Drug Des. 2014; 83: 450
• 2b Bauer MR, Fruscia PD, Lucas SC. C, Michaelides IN, Nelson JE, Storer RI, Whitehurst BC. RSC Med. Chem. 2021; 12: 448
• 3a Freire E. Drug Discovery Today 2008; 13: 869
• 3b Hopkins AL, Keserü GM, Leeson PD, Rees DC, Reynolds CH. Nat. Rev. Drug Discovery 2014; 13: 105
• 3c Mignani S, Rodrigues J, Tomas H, Jalal R, Singh PP, Majoral J.-P, Vishwakarma RA. Drug Discovery Today 2018; 23: 605

For reviews on the catalytic dearomative functionalizations of arenes, see:
• 4a Porco JA. Jr, Roche SP. Angew. Chem. Int. Ed. 2011; 50: 4068
• 4b Zhuo C.-X, Zhang W, You S.-L. Angew. Chem. Int. Ed. 2012; 51: 12662
• 4c Ding Q, Zhou X, Fan R. Org. Biomol. Chem. 2014; 12: 4807
• 4d Wu W.-T, Zhang L, You S.-L. Chem. Soc. Rev. 2016; 45: 1570
• 4e Wertjes WC, Southgate EH, Sarlah D. Chem. Soc. Rev. 2018; 47: 7996
• 4f Okumura M, Sarlah D. Eur. J. Org. Chem. 2020; 10: 1259
• 4g Huck CJ, Sarlah D. Chem 2020; 6: 1589
• 4h Zheng C, You S.-L. ACS Cent. Sci. 2021; 7: 432
• 4i Zhang Z, Han H, Wang L, Bu Z, Xie Y, Wang Q. Org. Biomol. Chem. 2021; 19: 3960
• 4j Cheng Y.-Z, Feng Z, Zhang X, You S.-L. Chem. Soc. Rev. 2022; 51: 2145
• 4k Kratena N, Marinic B, Donohoe TJ. Chem. Sci. 2022; 13: 14213
• 4l Liu Y.-Z, Song H, Zheng C, You S.-L. Nat. Synth. 2022; 1: 203
• 4m Palai A, Rai P, Maji B. Chem. Sci. 2023; 14: 12004
• 4n Ji P, Duan K, Li M, Wang Z, Meng X, Zhang Y, Wang W. Chem. Soc. Rev. 2024; 53: 6600

For reviews on the nucleophilic dearomative functionalizations of arenes, see:
• 5a Ortiz FL, Iglesias MJ, Fernández I, Sánchez CM. A, Gómez GR. Chem. Rev. 2007; 107: 1580
• 5b Bertuzzi G, Bernardi L, Fochi M. Catalysts 2018; 8: 632
• 5c Escolano M, Gavina D, Alzuet-Piña G, Díaz-Oltra S, Sánchez-Roselló M, Pozo C. Chem. Rev. 2024; 124: 1122
• 6a O’Hagan D. Nat. Prod. Rep. 2000; 17: 435
• 6b Sridharan V, Suryavanshi PA, Meneńdez JC. Chem. Rev. 2011; 111: 7157
• 6c Muthukrishnan I, Sridharan V, Meneńdez JC. Chem. Rev. 2019; 119: 5057

For a review, see:
• 7a Mariano PS. Tetrahedron 1983; 39: 3845

For early reports, see:
• 7b Stermitz FR, Wei CC, O’Donnell CM. J. Am. Chem. Soc. 1970; 92: 2745
• 7c Sugimori A, Yamada T, Ishida H, Nose M, Terashima K, Oohata N. Bull. Chem. Soc. Jpn. 1986; 59: 3905

For recent reports, see:
• 7d Liu W, Yang X, Zhou Z.-Z, Li C.-J. Chem 2017; 2: 688
• 7e McCallum T, Pitre SP, Morin M, Scaiano JC, Barriault L. Chem. Sci. 2017; 8: 7412
• 8 Hu C, Vo C, Merchant RR, Chen S.-J, Hughes JM. E, Peters BK, Qin T. J. Am. Chem. Soc. 2023; 145: 25
• 9a Koike T, Akita T. Inorg. Chem. Front. 2014; 1: 562
• 9b Strieth-Kalthoff F, James MJ, Teders M, Pitzer L, Glorius F. Chem. Soc. Rev. 2018; 47: 7190
• 9c Bell JD, Murphy JA. Chem. Soc. Rev. 2021; 50: 9540
• 9d Wu Y, Kim D, Teets TS. Synlett 2022; 33: 1154
• 9e Dutta S, Erchinger JE, Strieth-Kalthoff F, Kleinmans R, Glorius F. Chem. Soc. Rev. 2024; 53: 1068
• 10 Ma J, Chen S, Bellotti P, Guo R, Schäfer F, Heusler A, Zhang X, Daniliuc C, Brown MK, Houk KN, Glorius F. Science 2021; 371: 1338
• 11 Guo R, Adak S, Bellotti P, Gao X, Smith WW, Le SN, Ma J, Houk KN, Glorius F, Chen S, Brown MK. J. Am. Chem. Soc. 2022; 144: 17680
• 12 Morofuji T, Nagai S, Chitose Y, Abe M, Kano N. Org. Lett. 2021; 23: 6257
• 13 Bhakat M, Khatua B, Biswas P, Guin J. Org. Lett. 2023; 25: 3089
• 14 Ma J, Chen S, Bellotti P, Wagener T, Daniliuc C, Houk KN, Glorius F. Nat. Catal. 2022; 5: 405
• 15 Kleinmans R, Dutta S, Ozols K, Shao H, Schäfer F, Thielemann RE, Chan HT, Daniliuc CG, Houk KN, Glorius F. J. Am. Chem. Soc. 2023; 145: 12324
• 16 Ji P, Davies CC, Gao F, Chen J, Meng X, Houk KN, Chen S, Wang W. Nat. Commun. 2022; 13: 4565
• 17 Tan EY. K, Dehdari A, Lani AS. M, Pratt DA, Chiba S. Chem 2024; 10: 3722
• 18a Southgate EH, Pospech J, Fu J, Holycross DR, Sarlah D. Nat. Chem. 2016; 8: 922
• 18b Okumura M, Huynh SM. N, Pospech J, Sarlah D. Angew. Chem. Int. Ed. 2016; 55: 15910
• 18c Hernandez LW, Klöckner U, Pospech J, Hauss L, Sarlah D. J. Am. Chem. Soc. 2018; 140: 4503
• 18d Wertjes WC, Okumura M, Sarlah D. J. Am. Chem. Soc. 2019; 141: 163
• 18e Tnag C, Okumura M, Zhu Y, Hooper AR, Zhou Y, Lee Y.-H, Sarlah D. Angew. Chem. Int. Ed. 2019; 58: 10245
• 18f Tnag C, Okumura M, Deng H, Sarlah D. Angew. Chem. Int. Ed. 2019; 58: 15762
• 18g Davis CW, Zhang Y, Li Y, Martinelli M, Zhang J, Ungarean C, Galer P, Liu P, Sarlah D. Angew. Chem. Int. Ed. 2024; 63: e202407281
• 18h Davis CW, Li Y, Zhang Y, Siddiqu Z, Liu P, Sarlah D. ACS Catal. 2024; 14: 10132
• 18i Gilbert R, Davis CW, Bingham TW, Sarlah D. Tetrahedron 2024; 163: 134135
• 18j Siddiqi Z, Wertjes WC, Sarlah D. J. Am. Chem. Soc. 2020; 142: 10125
• 18k Piacentini P, Bingham TW, Sarlah D. Angew. Chem. Int. Ed. 2022; 61: e202208014
• 19 Ikeda K, Kojima R, Kawai K, Murakami T, Kikuchi T, Kojima M, Yoshino T, Matsunaga S. J. Am. Chem. Soc. 2023; 145: 9326
• 20 Leitch JA, Rogova T, Duarte F, Dixon DJ. Angew. Chem. Int. Ed. 2020; 59: 4121
• 21 Ishigaki S, Nagashima Y, Yukimori D, Tanaka J, Matsumoto T, Miyamoto K, Uchiyama M, Tanaka K. Nat. Commun. 2023; 14: 652
• 22 Shimose A, Ishigaki S, Sato Y, Nogami J, Toriumi N, Uchiyama M, Tanaka K, Nagashima Y. Angew. Chem. Int. Ed. 2024; 63: e202403461
• 23a Yukimori D, Nagashima Y, Wang C, Muranaka A, Uchiyama M. J. Am. Chem. Soc. 2019; 141: 9819
• 23b Sakamoto K, Nagashima Y, Wang C, Miyamoto K, Tanaka K, Uchiyama M. J. Am. Chem. Soc. 2021; 143: 5629
• 23c Arai R, Nagashima Y, Koshikawa T, Tanaka K. J. Org. Chem. 2023; 88: 10371
• 23d Komaki T, Sato Y, Uchiyama M, Tanaka K, Nagashima Y. Org. Lett. 2024; 26: 2180
• 23e Iimuro H, Ishigaki S, Dias AJ. A, Inoue T, Tanaka K, Nagashima Y. J. Org. Chem. 2024; 89: 15623

For reviews on silyl radicals, see:
• 24a Chatgilialoglu C. Chem. Rev. 1995; 95: 1229
• 24b Chatgilialoglu C, Lalevée J. Molecules 2012; 17: 527
• 24c Chatgilialoglu C, Ferreri C, Landais Y, Timokhin VI. Chem. Rev. 2018; 118: 6516
• 24d Li J.-S, Wu J. ChemPhotoChem 2018; 2: 839
• 24e Ghosh S, Lai D, Hajra A. Org. Biomol. Chem. 2021; 19: 2399
• 24f Biremond T, Riomet M, Jubault P, Poisson T. Chem. Rec. 2023; 10: e202300172
• 25 Maeda S, Ohno K, Morokuma K. Phys. Chem. Chem. Phys. 2013; 15: 3683