Basic Concepts and Activation Modes in Visible-Light-Photocatalyzed Organic Synthesis

Visible light photocatalysis has established itself as a promising sustainable and powerful strategy to access reactive intermediates, i.e. radicals and radical ions, under mild reaction conditions using visible light irradiation. This field enables the development of formerly challenging or even previously inaccessible organic transformations. In this tutorial review, an overview of the essential concepts and techniques of visible-light-mediated chemical processes and the most common types of photochemical activation of organic molecules, i.e. photoredox catalysis and photosensitization, are discussed. Selected photocatalytic alkene functionalization reactions are included as examples to illustrate the basic concepts and techniques with particular attention given to the understanding of their reaction mechanisms.

1 Introduction

2 Photocatalysts

3 Photophysical and Electrochemical Properties

3.1 Excited-State Energy

3.2 Ground-State Redox Potentials

3.3 Excited-State Redox Potentials

3.4 Local Absorbance Maximum for Lowest Energy Absorption

3.5 Excited-State Lifetime

3.6 [Ru(bpy)₃]²⁺ as a Case Study

3.7 Basic Laws and Equations of Photochemistry and Photocatalysis

3.8 Common Terminology in Photochemistry and Photocatalysis

4 Activation Modes in Photocatalysis

4.1 Photoinduced Electron Transfer

4.2 Photoinduced Energy Transfer

5 Conclusions and Outlook

Keywords

visible light - photocatalyst - excited state - redox potential - PET (photoinduced electron transfer) - EnT (photoinduced energy transfer)

Full Text

References

References

1a Poplata S, Tröster A, Zou Y.-Q, Bach T. Chem. Rev. 2016; 116: 9748
1b Mangion IK, MacMillan DW. C. J. Am. Chem. Soc. 2005; 127: 3696
1c Liu H.-J, Lee SP. Tetrahedron Lett. 1977; 18: 3699

2a Kärkäs MD, Porco JA, Stephenson CR. J. Chem. Rev. 2016; 116: 9683
2b Bach T, Hehn JP. Angew. Chem. Int. Ed. 2011; 50: 1000
2c Nicolaou KC, Gray DL. F, Tae J. J. Am. Chem. Soc. 2004; 126: 613
2d Renata H, Zhou Q, Baran PS. Science 2013; 339: 59

3 Marzo L, Pagire SK, Reiser O, König B. Angew. Chem. Int. Ed. 2018; 57: 10034
4 Bell JD, Murphy JA. Chem. Soc. Rev. 2021; 50: 9540
5 Strieth-Kalthoff F, James MJ, Teders M, Pitzer L, Glorius F. Chem. Soc. Rev. 2018; 47: 7190
6 Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102
7 McAtee RC, McClain EJ, Stephenson CR. J. Trends Chem. 2019; 1: 111
8 Ciamician G. Science 1912; 36: 385

9a Zeitler K. Angew. Chem. Int. Ed. 2009; 48: 9785
9b Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
9c Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
9d Wang C.-S, Dixneuf PH, Soulé J.-F. Chem. Rev. 2018; 118: 7532
9e Cauwenbergh R, Das S. Synlett 2022; 33: 129

10a Miller DC, Tarantino KT, Knowles RR. Top. Curr. Chem. 2016; 374: 30
10b Murray PR. D, Cox JH, Chiappini ND, Roos CB, McLoughlin EA, Hejna BG, Nguyen ST, Ripberger HH, Ganley JM, Tsui E, Shin NY, Koronkiewicz B, Qiu G, Knowles RR. Chem. Rev. 2022; 122: 2017

11 Capaldo L, Ravelli D, Fagnoni M. Chem. Rev. 2022; 122: 1875

12a Zhou Q.-Q, Zou Y.-Q, Lu L.-Q, Xiao W.-J. Angew. Chem. Int. Ed. 2019; 58: 1586
12b Strieth-Kalthoff F, Glorius F. Chem 2020; 6: 1888

13a Wei Y, Zhou Q.-Q, Tan F, Lu L.-Q, Xiao W.-J. Synthesis 2019; 51: 3021
13b Crisenza GE. M, Mazzarella D, Melchiorre P. J. Am. Chem. Soc. 2020; 142: 5461
13c Sumida Y, Ohmiya H. Chem. Soc. Rev. 2021; 50: 6320
13d Tasnim T, Ayodele MJ, Pitre SP. J. Org. Chem. 2022; 87: 10555

14a Kancherla R, Muralirajan K, Sagadevan A, Rueping M. Trends Chem. 2019; 1: 510
14b Cheung KP. S, Sarkar S, Gevorgyan V. Chem. Rev. 2022; 122: 1543
14c Sarkar T, Shah TA, Maharana PK, Debnath B, Punniyamurthy T. Eur. J. Org. Chem. 2022; in press

15a Arias-Rotondo DM, McCusker JK. Chem. Soc. Rev. 2016; 45: 5803
15b Hockin BM, Li C, Robertson N, Zysman-Colman E. Catal. Sci. Technol. 2019; 9: 889

16a Bryden MA, Zysman-Colman E. Chem. Soc. Rev. 2021; 50: 7587
16b Vega-Peñaloza A, Mateos J, Companyó X, Escudero-Casao M, Dell’Amico L. Angew. Chem. Int. Ed. 2021; 60: 1082
16c Amos SG. E, Garreau M, Buzzetti L, Waser J. Beilstein J. Org. Chem. 2020; 16: 1163
16d Lee Y, Kwon MS. Eur. J. Org. Chem. 2020; 2020: 6028
16e Bobo MV, Kuchta JJ, Vannucci AK. Org. Biomol. Chem. 2021; 19: 4816

17a Riente P, Noël T. Catal. Sci. Technol. 2019; 9: 5186
17b Franchi D, Amara Z. ACS Sustainable Chem. Eng. 2020; 8: 15405

18 De Vos D, Gadde K, Maes BU. W. Synthesis 2022; in press,

19a Singh A, Teegardin K, Kelly M, Prasad KS, Krishnan S, Weaver JD. J. Organomet. Chem. 2015; 776: 51
19b Koike T, Akita M. Inorg. Chem. Front. 2014; 1: 562

20 Maes J, Mitchell EA, Maes BU. W. Base Metals in Catalysis: From Zero to Hero. In Green and Sustainable Medicinal Chemistry: Methods, Tools and Strategies for the 21st Century Pharmaceutical Industry, Chap. 16. Summerton L, Sneddon HF, Jones LC, Clark JH. Royal Society of Chemistry; Cambridge: 2016: 192-202

21a Paria S, Reiser O. ChemCatChem 2014; 6: 2477
21b Paria S, Reiser O. Visible Light and Copper Complexes: A Promising Match in Photoredox Catalysis. In Visible Light Photocatalysis in Organic Chemistry. Stephenson CR. J, Yoon TP, MacMillan DW. C. Wiley-VCH; Weinheim: 2018: 233-251
21c Hossain A, Bhattacharyya A, Reiser O. Science 2019; 364: eaav9713
21d Larsen CB, Wenger OS. Chem. Eur. J. 2018; 24: 2039
21e Wenger OS. J. Am. Chem. Soc. 2018; 140: 13522

22a Joshi-Pangu A, Lévesque F, Roth HG, Oliver SF, Campeau L.-C, Nicewicz D, DiRocco DA. J. Org. Chem. 2016; 81: 7244
22b Tlili A, Lakhdar S. Angew. Chem. Int. Ed. 2021; 60: 19526

23a Speckmeier E, Fischer TG, Zeitler K. J. Am. Chem. Soc. 2018; 140: 15353
23b Natarajan P, König B. Eur. J. Org. Chem. 2021; 2021: 2145

24 Hari DP, König B. Chem. Commun. 2014; 50: 6688
25 Gisbertz S, Pieber B. ChemPhotoChem 2020; 4: 456

26a Savateev A, Ghosh I, König B, Antonietti M. Angew. Chem. Int. Ed. 2018; 57: 15936
26b Savateev A, Antonietti M. ChemCatChem 2019; 11: 6166

27 Zhang T, Lin W. Chem. Soc. Rev. 2014; 43: 5982

28a Geng K, He T, Liu R, Dalapati S, Tan KT, Li Z, Tao S, Gong Y, Jiang Q, Jiang D. Chem. Rev. 2020; 120: 8814
28b Yang Q, Luo M, Liu K, Cao H, Yan H. Appl. Catal., B 2020; 276: 119174

29 Lan G, Quan Y, Wang M, Nash GT, You E, Song Y, Veroneau SS, Jiang X, Lin W. J. Am. Chem. Soc. 2019; 141: 15767
30 Knorn M, Rawner T, Czerwieniec R, Reiser O. ACS Catal. 2015; 5: 5186
31 Martiny M, Steckhan E, Esch T. Chem. Ber. 1993; 126: 1671
32 Kasha M. Discuss. Faraday Soc. 1950; 9: 14
33 Rey YP, Abradelo DG, Santschi N, Strassert CA, Gilmour R. Eur. J. Org. Chem. 2017; 2017: 2170

34a Elgrishi N, Rountree KJ, McCarthy BD, Rountree ES, Eisenhart TT, Dempsey JL. J. Chem. Educ. 2018; 95: 197
34b Roth HG, Romero NA, Nicewicz DA. Synlett 2016; 27: 714

35 Wu Y, Kim D, Teets TS. Synlett 2022; 33: 1154
36 Rehm D, Weller A. Isr. J. Chem. 1970; 8: 259
37 Campagna S, Puntoriero F, Nastasi F, Bergamini G, Balzani V. Photochemistry and Photophysics of Coordination Compounds: Ruthenium . In Photochemistry and Photophysics of Coordination Compounds I . Balzani V, Campagna S. Springer; Heidelberg: 2007: 117-214

38a Cismesia MA, Yoon TP. Chem. Sci. 2015; 6: 5426
38b Gadde K, Mampuys P, Guidetti A, Ching HY. V, Herrebout WA, Van Doorslaer S, Abbaspour Tehrani K, Maes BU. W. ACS Catal. 2020; 10: 8765

39a Gaida F, Griesbeck AG, Vollmer M. Photocatalysis: The Principles . In Science of Synthesis: Photocatalysis in Organic Synthesis, Chap. 3. König B. Thieme; Stuttgart: 2019: 3
39b Kuijpers KP. L, Bottecchia C, Cambié D, Drummen K, König NJ, Noël T. Angew. Chem. Int. Ed. 2018; 57: 11278

40 Żamojć K, Bylińska I, Wiczk W, Chmurzyński L. Int. J. Mol. Sci. 2021; 22: 885
41 IUPAC Compendium of Chemical Terminology, 2nd ed. McNaught AD, Wilkinson A. Blackwell Scientific; Oxford: 1997. https//goldbook.iupac.org(accessed Sept 15, 2022
42 Tibbetts JD, Bull SD. Adv. Sustainable Syst. 2021; 5: 2000292
43 Besson M, Gallezot P, Pinel C. Chem. Rev. 2014; 114: 1827
44 Beller M, Seayad J, Tillack A, Jiao H. Angew. Chem. Int. Ed. 2004; 43: 3368

45a Courant T, Masson G. J. Org. Chem. 2016; 81: 6945
45b Cao M.-Y, Ren X, Lu Z. Tetrahedron Lett. 2015; 56: 3732
45c Koike T, Akita M. Chem 2018; 4: 409

46a Cano-Yelo H, Deronzier A. J. Chem. Soc., Perkin Trans. 2 1984; 1093
46b Cano-Yelo H, Deronzier A. Tetrahedron Lett. 1984; 25: 5517
46c Cano-Yelo H, Deronzier A. J. Chem. Soc., Faraday Trans. 1 1984; 3011
46d Cano-Yelo H, Deronzier A. J. Photochem. 1987; 37: 315

47a Hironaka K, Fukuzumi S, Tanaka T. J. Chem. Soc., Perkin Trans. 2 1984; 1705
47b Ishikawa M, Fukuzumi S. J. Chem. Soc., Chem. Commun. 1990; 1353
47c Fukuzumi S, Mochizuki S, Tanaka T. J. Phys. Chem. 1990; 94: 722

48a Hedstrand DM, Kruizinga WH, Kellogg RM. Tetrahedron Lett. 1978; 19: 1255
48b Van Bergen TJ, Hedstrand DM, Kruizinga WH, Kellogg RM. J. Org. Chem. 1979; 44: 4953

49a Okada K, Okamoto K, Morita N, Okubo K, Oda M. J. Am. Chem. Soc. 1991; 113: 9401
49b Okada K, Okubo K, Morita N, Oda M. Tetrahedron Lett. 1992; 33: 7377

50a Pac C, Ihama M, Yasuda M, Miyauchi Y, Sakurai H. J. Am. Chem. Soc. 1981; 103: 6495
50b Ishitani O, Pac C, Sakurai H. J. Org. Chem. 1983; 48: 2941
50c Majima T, Pac C, Nakasone A, Sakurai H. J. Am. Chem. Soc. 1981; 103: 4499

51 Pandey G, Hajra S, Ghorai MK, Kumar KR. J. Am. Chem. Soc. 1997; 119: 8777
52 Tomioka H, Ueda K, Ohi H, Izawa Y. Chem. Lett. 1986; 15: 1359

53a Willner I, Tsfania T, Eichen Y. J. Org. Chem. 1990; 55: 2656
53b Mandler D, Willner I. J. Chem. Soc., Perkin Trans. 2 1986; 805
53c Mandler D, Willner I. J. Chem. Soc., Chem. Commun. 1986; 851

54 Ischay MA, Anzovino ME, Du J, Yoon TP. J. Am. Chem. Soc. 2008; 130: 12886
55 Nicewicz DA, MacMillan DW. C. Science 2008; 322: 77
56 Narayanam JM. R, Tucker JW, Stephenson CR. J. J. Am. Chem. Soc. 2009; 131: 8756
57 Marcus RA. Angew. Chem. Int. Ed. 1993; 32: 1111
58 Nguyen JD, Tucker JW, Konieczynska MD, Stephenson CR. J. J. Am. Chem. Soc. 2011; 133: 4160
59 Courant T, Masson G. Chem. Eur. J. 2012; 18: 423
60 Pirtsch M, Paria S, Matsuno T, Isobe H, Reiser O. Chem. Eur. J. 2012; 18: 7336
61 Hossain A, Engl S, Lutsker E, Reiser O. ACS Catal. 2019; 9: 1103
62 Engl S, Reiser O. Chem. Soc. Rev. 2022; 51: 5287
63 Huang H, Yu C, Zhang Y, Zhang Y, Mariano PS, Wang W. J. Am. Chem. Soc. 2017; 139: 9799
64 Riente P, Pericàs MA. ChemSusChem 2015; 8: 1841
65 Riente P, Fianchini M, Llanes P, Pericàs MA, Noël T. Nat. Commun. 2021; 12: 625
66 Mirkovic T, Ostroumov EE, Anna JM, van Grondelle R, Govindjee, Scholes GD. Chem. Rev. 2017; 117: 249

67a Yoo W.-J, Tsukamoto T, Kobayashi S. Org. Lett. 2015; 17: 3640
67b Heitz DR, Tellis JC, Molander GA. J. Am. Chem. Soc. 2016; 138: 12715

68 Neveselý T, Wienhold M, Molloy JJ, Gilmour R. Chem. Rev. 2022; 122: 2650
69 Chen D.-F, Chrisman CH, Miyake GM. ACS Catal. 2020; 10: 2609
70 Patra T, Bellotti P, Strieth-Kalthoff F, Glorius F. Angew. Chem. Int. Ed. 2020; 59: 3172
71 Prat D, Wells A, Hayler J, Sneddon H, McElroy CR, Abou-Shehada S, Dunn PJ. Green Chem. 2016; 18: 288

72a McElroy CR, Constantinou A, Jones LC, Summerton L, Clark JH. Green Chem. 2015; 17: 3111
72b Abou-Shehada S, Mampuys P, Maes BU. W, Clark JH, Summerton L. Green Chem. 2017; 19: 249

73 Monteith ER, Mampuys P, Summerton L, Clark JH, Maes BU. W, McElroy CR. Green Chem. 2020; 22: 123
74 Pitzer L, Schäfers F, Glorius F. Angew. Chem. Int. Ed. 2019; 58: 8572
75 Novaes LF. T, Liu J, Shen Y, Lu L, Meinhardt JM, Lin S. Chem. Soc. Rev. 2021; 50: 7941
76 Sambiagio C, Sterckx H, Maes BU. W. ACS Cent. Sci. 2017; 3: 686