Catalyst-Free Photoinduced C–C Bond Formations

Shyamal Kanti Bera; Rosalin Bhanja; Prasenjit Mal

doi:10.1055/a-2043-3973

Synthesis, Table of Contents

Synthesis 2023; 55(10): 1467-1486
DOI: 10.1055/a-2043-3973

review

Catalyst-Free Photoinduced C–C Bond Formations

Shyamal Kanti Bera ‡

,

Rosalin Bhanja ‡

,

Prasenjit Mal ∗

Abstract

All articles of this category

Abstract

Use of sustainable energy sources in synthetic organic chemistry has become one of the most popular research topics due to environmental pollution and global warming. In this review, we discuss photocatalyst-free and transition-metal-free light-induced reactions for the construction of carbon–carbon (C–C) bonds. The reaction systems discussed here are C–C bond formation via carbene intermediates, radical intermediates, and miscellaneous reactions via cyclization.

1 Introduction

2 C–C Bond Formation via Carbene Intermediates

3 C–C Bond Formation via Radical Intermediates

4 Miscellaneous C–C Bond Formation via Cyclization

5 Conclusion

Key words

C–C bond formation - catalyst-free - transition-metal-free - photoinduced - visible light - carbene - radical

Full Text

References

References
1 Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
2 Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102
3 Yoon TP, Ischay MA, Du J. Nat. Chem. 2010; 2: 527
4 Marzo L, Pagire SK, Reiser O, König B. Angew. Chem. Int. Ed. 2018; 57: 10034
5 Zuin VG, Eilks I, Elschami M, Kümmerer K. Green Chem. 2021; 23: 1594

6a Wang Z. In Comprehensive Organic Name Reactions and Reagents. Wiley; Hoboken: 2010: 2062
6b Armesto D, Ortiz MJ, Agarrabeitia AR, Martín-Fontecha M. Org. Lett. 2005; 7: 2687

7a Yamada S, Iwaoka A, Fujita Y, Tsuzuki S. Org. Lett. 2013; 15: 5994
7b Singhal N, Koner AL, Mal P, Venugopalan P, Nau WM, Moorthy JN. J. Am. Chem. Soc. 2005; 127: 14375

8 D’Auria M. Photochem. Photobiol. Sci. 2019; 18: 2297

9a Gadde K, De Vos D, Maes BU. W. Synthesis 2023; 55: 193
9b Vanderghinste J, Das S. Synthesis 2022; 54: 3383
9c Sakakibara Y, Murakami K. ACS Catal. 2022; 12: 1857
9d Chan AY, Perry IB, Bissonnette NB, Buksh BF, Edwards GA, Frye LI, Garry OL, Lavagnino MN, Li BX, Liang Y, Mao E, Millet A, Oakley JV, Reed NL, Sakai HA, Seath CP, MacMillan DW. C. Chem. Rev. 2022; 122: 1485
9e Tan H, Li H, Ji W, Wang L, Wang L. Angew. Chem. Int. Ed. 2015; 54: 8374

10 Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322

11a Ardila-Fierro KJ, Hernández JG. ChemSusChem 2021; 14: 2145
11b Song J, Han B. Natl. Sci. Rev. 2014; 2: 255

12a Holmberg-Douglas N, Nicewicz DA. Chem. Rev. 2022; 122: 1925
12b Bose A, Mal P. ARKIVOC 2021; (vii): 79
12c Sau S, Mal P. J. Org. Chem. 2022; 87: 14565
12d Pramanik M, Choudhuri K, Mathuri A, Mal P. Chem. Commun. 2020; 56: 10211
12e Pramanik M, Mathuri A, Sau S, Das M, Mal P. Org. Lett. 2021; 23: 8088

13 Fan X.-Z, Rong J.-W, Wu H.-L, Zhou Q, Deng H.-P, Tan JD, Xue C.-W, Wu L.-Z, Tao H.-R, Wu J. Angew. Chem. Int. Ed. 2018; 57: 8514

14a Sharma S, Sharma A. Org. Biomol. Chem. 2019; 17: 4384
14b Kibriya G, Mondal S, Hajra A. Org. Lett. 2018; 20: 7740

15a MacKenzie IA, Wang L, Onuska NP. R, Williams OF, Begam K, Moran AM, Dunietz BD, Nicewicz DA. Nature 2020; 580: 76
15b Mandal S, Bhuyan S, Jana S, Hossain J, Chhetri K, Roy BG. Green Chem. 2021; 23: 5049

16 Tlili A, Lakhdar S. Angew. Chem. Int. Ed. 2021; 60: 19526
17 Patel RI, Sharma A, Sharma S, Sharma A. Org. Chem. Front. 2021; 8: 1694

18a Bera SK, Boruah PJ, Parida SS, Paul AK, Mal P. J. Org. Chem. 2021; 86: 9587
18b Yuan Y.-q, Majumder S, Yang M.-h, Guo S.-r. Tetrahedron Lett. 2020; 61: 151506
18c Saikia BS, Deb ML, Baruah PK. Environ. Chem. Lett. 2022; 20: 109
18d Saikia BS, Borpatra PJ, Rahman I, Deb ML, Baruah PK. New J. Chem. 2022; 46: 16523

19a Zeitler K. Angew. Chem. Int. Ed. 2009; 48: 9785
19b Schultz DM, Yoon TP. Science 2014; 343: 985

20 Ravelli D, Protti S, Fagnoni M. Chem. Rev. 2016; 116: 9850
21 Crisenza GE. M, Mazzarella D, Melchiorre P. J. Am. Chem. Soc. 2020; 142: 5461

22a Qin C, Boyarskikh V, Hansen JH, Hardcastle KI, Musaev DG, Davies HM. L. J. Am. Chem. Soc. 2011; 133: 19198
22b Zhang Y, Yao Y, He L, Liu Y, Shi L. Adv. Synth. Catal. 2017; 359: 2754
22c Arredondo V, Hiew SC, Gutman ES, Premachandra ID. U. A, Van Vranken DL. Angew. Chem. Int. Ed. 2017; 56: 4156
22d Liao K, Negretti S, Musaev DG, Bacsa J, Davies HM. L. Nature 2016; 533: 230

23 Xiang Y, Wang C, Ding Q, Peng Y. Adv. Synth. Catal. 2019; 361: 919

24a Davies HM. L, Grazini MV. A, Aouad E. Org. Lett. 2001; 3: 1475
24b Rodríguez A, Nomen M, Spur BW, Godfroid J.-J. Eur. J. Org. Chem. 1999; 2655

25 Yang Z, Stivanin ML, Jurberg ID, Koenigs RM. Chem. Soc. Rev. 2020; 49: 6833
26 Jurberg ID, Davies HM. L. Chem. Sci. 2018; 9: 5112
27 Xiao T, Mei M, He Y, Zhou L. Chem. Commun. 2018; 54: 8865
28 Guo Y, Nguyen TV, Koenigs RM. Org. Lett. 2019; 21: 8814
29 Hommelsheim R, Guo Y, Yang Z, Empel C, Koenigs RM. Angew. Chem. Int. Ed. 2019; 58: 1203
30 Li F, He F, Koenigs RM. Synthesis 2019; 51: 4348
31 Zhang Z, Yadagiri D, Gevorgyan V. Chem. Sci. 2019; 10: 8399
32 Zhang X, Du C, Zhang H, Li X.-C, Wang Y.-L, Niu J.-L, Song M.-P. Synthesis 2019; 51: 889
33 Jana S, Li F, Empel C, Verspeek D, Aseeva P, Koenigs RM. Chem. Eur. J. 2020; 26: 2586
34 da Silva AF, Afonso MA. S, Cormanich RA, Jurberg ID. Chem. Eur. J. 2020; 26: 5648
35 Barluenga J, Tomás-Gamasa M, Aznar F, Valdés C. Nat. Chem. 2009; 1: 494
36 Li W, Yang Y, Tang Z, Yu X, Lin J, Jin Y. J. Org. Chem. 2022; 87: 13352
37 Martin R, Buchwald SL. Acc. Chem. Res. 2008; 41: 1461
38 Cordovilla C, Bartolomé C, Martínez-Ilarduya JM, Espinet P. ACS Catal. 2015; 5: 3040
39 Sambiagio C, Marsden SP, Blacker AJ, McGowan PC. Chem. Soc. Rev. 2014; 43: 3525
40 Sun C.-L, Li H, Yu D.-G, Yu M, Zhou X, Lu X.-Y, Huang K, Zheng S.-F, Li B.-J, Shi Z.-J. Nat. Chem. 2010; 2: 1044
41 Ashenhurst JA. Chem. Soc. Rev. 2010; 39: 540
42 Kloss F, Neuwirth T, Haensch VG, Hertweck C. Angew. Chem. Int. Ed. 2018; 57: 14476
43 Jana S, Pei C, Bahukhandi SB, Koenigs RM. Chem Catal. 2021; 1: 467
44 Hsieh H.-W, Coley CW, Baumgartner LM, Jensen KF, Robinson RI. Org. Process Res. Dev. 2018; 22: 542
45 Gu L, Jin C, Liu J. Green Chem. 2015; 17: 3733
46 Rueping M, Zoller J, Fabry DC, Poscharny K, Koenigs RM, Weirich TE, Mayer J. Chem. Eur. J. 2012; 18: 3478
47 Fürst MC. D, Gans E, Böck MJ, Heinrich MR. Chem. Eur. J. 2017; 23: 15312
48 Cheng Y, Li G, Liu Y, Shi Y, Gao G, Wu D, Lan J, You J. J. Am. Chem. Soc. 2016; 138: 4730
49 Aganda KC. C, Kim J, Lee A. Org. Biomol. Chem. 2019; 17: 9698
50 Pan P, Liu S, Lan Y, Zeng H, Li C.-J. Chem. Sci. 2022; 13: 7165
51 Cao D, Ataya M, Chen Z, Zeng H, Peng Y, Khaliullin RZ, Li C.-J. Nat. Commun. 2022; 13: 1805
52 Bartolomeu AA, Silva RC, Brocksom TJ, Noel T, de Oliveira KT. J. Org. Chem. 2019; 84: 10459
53 Sivendran N, Belitz F, Sowa Prendes D, Manu Martínez Á, Schmid R, Gooßen LJ. Chem. Eur. J. 2022; 28: e202103669

54a Crespi S, Protti S, Fagnoni M. J. Org. Chem. 2016; 81: 9612
54b Qiu D, Lian C, Mao J, Fagnoni M, Protti S. J. Org. Chem. 2020; 85: 12813

55 Dossena A, Sampaolesi S, Palmieri A, Protti S, Fagnoni M. J. Org. Chem. 2017; 82: 10687
56 Onuigbo L, Raviola C, Di Fonzo A, Protti S, Fagnoni M. Eur. J. Org. Chem. 2018; 5297
57 Zhang HH, Yu S. Org. Lett. 2019; 21: 3711
58 Chidley T, Jameel I, Rizwan S, Peixoto PA, Pouysegu L, Quideau S, Hopkins WS, Murphy GK. Angew. Chem. Int. Ed. 2019; 58: 16959
59 Liang K, Li N, Zhang Y, Li T, Xia C. Chem. Sci. 2019; 10: 3049
60 Kosynkin D, Bockman TM, Kochi JK. J. Am. Chem. Soc. 1997; 119: 4846
61 Liu Y, Li H, Chiba S. Org. Lett. 2021; 23: 427
62 Hayashi H, Wang B, Wu X, Teo SJ, Kaga A, Watanabe K, Takita R, Yeow EK. L, Chiba S. Adv. Synth. Catal. 2020; 362: 2223
63 Terlizzi LD, Cola I, Raviola C, Fagnoni M, Protti S. ACS Org. Inorg. Au 2021; 1: 68
64 Li Z, Ma P, Tan Y, Liu Y, Gao M, Zhang Y, Yang B, Huang X, Gao Y, Zhang J. Green Chem. 2020; 22: 646
65 Xu C, Shen F.-Q, Feng G, Jin J. Org. Lett. 2021; 23: 3913
66 Kaur J, Shahin A, Barham JP. Org. Lett. 2021; 23: 2002
67 Diesendorf N, Wenisch P, Oppl J, Heinrich MR. Org. Lett. 2023; 25: 76
68 Li Y, Liang X, Niu K, Gu J, Liu F, Xia Q, Wang Q, Zhang W. Org. Lett. 2022; 24: 5918
69 Wang X, Shao X, Cao Z, Wu X, Zhu C. Adv. Synth. Catal. 2022; 364: 1200
70 Ojima I, Tzamarioudaki M, Li Z, Donovan RJ. Chem. Rev. 1996; 96: 635
71 Chen H, Yu S. Org. Biomol. Chem. 2020; 18: 4519
72 Guerra WD, Rossi RA, Pierini AB, Barolo SM. J. Org. Chem. 2016; 81: 4965

73a Frontier AJ, Collison C. Tetrahedron 2005; 61: 7577
73b Dreger A, Wonner P, Engelage E, Walter SM, Stoll R, Huber SM. Chem. Commun. 2019; 55: 8262

74 Cai S, Xiao Z, Ou J, Shi Y, Gao S. Org. Chem. Front. 2016; 3: 354
75 Lvov AG, Shirinian VZ, Zakharov AV, Krayushkin MM, Kachala VV, Zavarzin IV. J. Org. Chem. 2015; 80: 11491
76 Fan J, Wang T, Li C, Wang R, Lei X, Liang Y, Zhang Z. Org. Lett. 2017; 19: 5984
77 Zhang J, Zhang X, Wang T, Yao X, Wang P, Wang P, Jing S, Liang Y, Zhang Z. J. Org. Chem. 2017; 82: 12097
78 Kang Y, Zhang W, Wang T, Liang Y, Zhang Z. J. Org. Chem. 2019; 84: 12387
79 Fan J, Zhang W, Gao W, Wang T, Duan WL, Liang Y, Zhang Z. Org. Lett. 2019; 21: 9183
80 Kang Y, Wang T, Liang Y, Zhang Y, Wang R, Zhang Z. RSC Adv. 2017; 7: 44333
81 Romero IE, Lantaño B, Postigo A, Bonesi SM. J. Org. Chem. 2022; 87: 13439
82 Di Sabato A, D’Acunzo F, Filippini D, Vetica F, Brasiello A, Corinti D, Bodo E, Michenzi C, Panzetta E, Gentili P. J. Org. Chem. 2022; 87: 13803