Carbonyl-Photoredox/Metal Dual Catalysis: Applications in Organic Synthesis

Photoredox/metal dual catalysis is a versatile tandem methodology to construct carbon–carbon and carbon–heteroatom bonds. The focus of this short review is the application of this technology to C(sp³)–C(sp³), C(sp³)–C(sp²), C(sp²)–C(sp²), C(sp²)–O, and C(sp³)–O bond formation induced by readily available and inexpensive carbonyl complexes as single electron transfer agents, photosensitizers, or hydrogen atom transfer agents.

1 Introduction

2 Homocoupling of Aryl Halides

3 Functionalization of C(sp³)–H Bonds

3.1 Dehydrogenation of Alkanes

3.2 Arylation/Alkylation

3.3 Carboxylation

3.4 Acylation

3.5 Hydroalkylation of Olefins

3.6 Hydroalkylation of Imines

4 Benzoylation of Aryl Bromides

5 Aryl Esterification

6 Oxidation of β-Keto Esters

7 Conclusions and Future Outlook

Key words

dual catalysis - carbonyl-photocatalysis - transition-metal catalysis - C–C bond - C–O bond

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References

1a Fabry DC, Rueping M. Acc. Chem. Res. 2016; 49: 1969
1b Zhang G, Liu C, Yi H, Meng Q, Bian C, Chen H, Jian J.-X, Wu L.-Z, Lei A. J. Am. Chem. Soc. 2015; 137: 9273
1c Huang H, Li X, Yu C, Zhang Y, Mariano PS, Wang W. Angew. Chem. Int. Ed. 2017; 56: 1500
1d Lang X, Zhao J, Chen X. Chem. Soc. Rev. 2016; 45: 3026
1e Abreu MD, Belmont P, Brachet E. Eur. J. Org. Chem. 2020; 1327

2a Tellis JC, Primer DN, Molander GA. Science 2014; 345: 433
2b Sharma UK, Gemoets HP. L, Schröder F, Noël T, Van der Eycken EV. ACS Catal. 2017; 7: 3818
2c Skubi KL, Blum TR, Yoon TP. Chem. Rev. 2016; 116: 10035
2d Cavedon C, Seeberger PH, Pieber B. Eur. J. Org. Chem. 2019; 1379

3a Twilton J, Le C, Zhang P, Shaw MH, Evans RW, MacMillan DW. C. Nat. Rev. Chem. 2017; 1: 0052
3b Zheng S, Primer DN, Molander GA. ACS Catal. 2017; 7: 7957
3c Sha W, Deng L, Ni S, Mei H, Han J, Pan Y. ACS Catal. 2018; 8: 7489
3d Yu W, Chen L, Tao J, Wang T, Fu J. Chem. Commun. 2019; 55: 5918
3e Gualandi A, Rodeghiero G, Faraone A, Patuzzo F, Marchini M, Calogero F, Perciaccante R, Jansen TP, Ceroni P, Cozzi PG. Chem. Commun. 2019; 55: 6838
3f Peng L, Li Z, Yin G. Org. Lett. 2018; 20: 1880

4a Kang B, Hong SH. Chem. Sci. 2017; 8: 6613
4b Vila C. ChemCatChem 2015; 7: 1790
4c Deng H.-P, Fan X.-Z, Chen Z.-H, Xu Q.-H, Wu J. J. Am. Chem. Soc. 2017; 139: 13579
4d Oderinde MS, Jones NH, Juneau A, Frenette M, Aquila B, Tentarelli S, Robbins DW, Johannes JW. Angew. Chem. Int. Ed. 2016; 55: 13219
4e Cheng W.-M, Shang R, Yu H.-Z, Fu Y. Chem. Eur. J. 2015; 21: 13191
4f Shu X.-z, Zhang M, He Y, Frei H, Toste FD. J. Am. Chem. Soc. 2014; 136: 5844

5a McLean EB, Lee A.-L. Tetrahedron 2018; 74: 4881
5b Teegardin K, Day JI, Chan J, Weaver J. Org. Process Res. Dev. 2016; 20: 1156
5c Till NA, Smith RT, MacMillan DW. C. J. Am. Chem. Soc. 2018; 140: 5701
5d Qu C, Zhang S, Du H, Zhu C. Chem. Commun. 2016; 52: 14400
5e Lang SB, O’Nele KM, Douglas JT, Tunge JA. Chem. Eur. J. 2015; 21: 18589
5f Tasker SZ, Jamison TF. J. Am. Chem. Soc. 2015; 137: 9531
5g Zhou Q.-Q, Zou Y.-Q, Lu L.-Q, Xiao W.-J. Angew. Chem. Int. Ed. 2019; 58: 1586

6a Mao R, Frey A, Balon J, Hu X. Nat. Catal. 2018; 1: 120
6b García-Domínguez A, Mondal R, Nevado C. Angew. Chem. Int. Ed. 2019; 58: 12286
6c Song F, Wang F, Guo L, Feng X, Zhang Y, Chu L. Angew. Chem. Int. Ed. 2020; 59: 177
6d Yang X.-L, Guo J.-D, Lei T, Chen B, Tung C.-H, Wu L.-Z. Org. Lett. 2018; 20: 2916
6e González MJ, Breit B. Chem. Eur. J. 2019; 25: 15746
6f Paul A, Smith MD, Vannucci AK. J. Org. Chem. 2017; 82: 1996

7a Kuang Y, Wang K, Shi X, Huang X, Meggers E, Wu J. Angew. Chem. Int. Ed. 2019; 58: 16859
7b Jeon J, He Y.-T, Shin S, Hong S. Angew. Chem. Int. Ed. 2020; 59: 281
7c Bonesi SM, Fagnoni M, Albini A. J. Org. Chem. 2004; 69: 928
7d Kalsi D, Dutta S, Barsu N, Rueping M, Sundararaju B. ACS Catal. 2018; 8: 8115
7e Meng Q.-Y, Wang S, König B. Angew. Chem. Int. Ed. 2017; 56: 13426

8a Tóth BL, Tischler O, Novák Z. Tetrahedron Lett. 2016; 57: 4505
8b Huang H, Jia K, Chen Y. ACS Catal. 2016; 6: 4983
8c Ruan L, Dong Z, Chen C, Wu S, Sun J. Chin. J. Org. Chem. 2017; 37: 2544

9 Luo J, Zhang J. ACS Catal. 2016; 6: 873

10a Arceo E, Montroni E, Melchiorre P. Angew. Chem. Int. Ed. 2014; 53: 12064
10b Nagatomo M, Yoshioka S, Inoue M. Chem. Asian J. 2015; 10: 120
10c Chen C. Org. Biomol. Chem. 2016; 14: 8641
10d Nikitas NF, Tzaras DI, Triandafillidi I, Kokotos CG. Green Chem. 2020; 22: 471

11a Shi Q, Ye J. Angew. Chem. Int. Ed. 2020; 59: 4998
11b Bume DD, Pitts CR, Ghorbani F, Harry SA, Capilato JN, Siegler MA, Lectka T. Chem. Sci. 2017; 8: 6918
11c Lipp A, Lahm G, Opatz T. J. Org. Chem. 2016; 81: 4890

12a Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
12b Fujiya A, Nobuta T, Yamaguchi E, Tada N, Miura T, Itoh A. RSC Adv. 2015; 5: 39539

13a Timpe H.-J, Kronfeld K.-P. J. Photochem. Photobiol. A 1989; 46: 253
13b Leigh WJ, Arnold DR, Humphreys RW. R, Wong PC. Can. J. Chem. 1980; 58: 2537
13c Strieth-Kalthoff F, James MJ, Teders M, Pitzer L, Glorius F. Chem. Soc. Rev. 2018; 47: 7190
13d Kearns DR, Case WA. J. Am. Chem. Soc. 1966; 88: 5087
13e Arnold DR. Adv. Photochem. 1968; 6: 301

14 Gentry EC, Knowles RR. Acc. Chem. Res. 2016; 49: 1546

15a Wagner PJ, Truman RJ, Scaiano JC. J. Am. Chem. Soc. 1985; 107: 7093
15b Kamijo S, Takao G, Kamijo K, Hirota M, Tao K, Murafuji T. Angew. Chem. Int. Ed. 2016; 55: 9695
15c Kamijo S, Hoshikawa T, Inoue M. Org. Lett. 2011; 13: 5928
15d Xia J.-B, Zhu C, Chen C. J. Am. Chem. Soc. 2013; 135: 17494

16a Ortica F, Romani A, Favaro G. J. Phys. Chem. A 1999; 103: 1335
16b Manfrotto C, Mella M, Freccero M, Fagnoni M, Albini A. J. Org. Chem. 1999; 64: 5024
16c Paul S, Guin J. Green Chem. 2017; 19: 2530
16d Ohkubo K, Hirose K, Fukuzumi S. Photochem. Photobiol. Sci. 2016; 15: 731

17a Kamijo S, Watanabe M, Kamijo K, Tao K, Murafuji T. Synthesis 2016; 48: 115
17b Bauer A, Westkamper F, Grimme S, Bach T. Nature 2005; 436: 1139
17c Capaldo L, Ravelli D. Eur. J. Org. Chem. 2017; 2056

18a Albini A. Synthesis 1981; 249
18b Tröster A, Alonso R, Bauer A, Bach T. J. Am. Chem. Soc. 2016; 138: 7808
18c Iyer A, Clay A, Jockusch S, Sivaguru J. J. Phys. Org. Chem. 2017; 30: e3738

19a Poplata S, Tröster A, Zou Y.-Q, Bach T. Chem. Rev. 2016; 116: 9748
19b Neveselý T, Daniliuc CG, Gilmour R. Org. Lett. 2019; 21: 9724

20a Hoffmann N. Synthesis 2016; 48: 1782
20b Schaefer CG, Peters KS. J. Am. Chem. Soc. 1980; 102: 7566
20c Yamashita T, Yasuda M, Watanabe M, Kojima R, Tanabe K, Shima K. J. Org. Chem. 1996; 61: 6438

21a Tripathi CB, Ohtani T, Corbett MT, Ooi T. Chem. Sci. 2017; 8: 5622
21b Harakat D, Pesch J, Marinkovic S, Hoffmann N. Org. Biomol. Chem. 2006; 4: 1202
21c Li L, Mu X, Liu W, Wang Y, Mi Z, Li C.-J. J. Am. Chem. Soc. 2016; 138: 5809
21d Bertrand S, Glapski C, Hoffmann N, Pete J.-P. Tetrahedron Lett. 1999; 40: 3169

22 Jones GH, Edwards DW, Par D. J. Chem. Soc., Chem. Commun. 1976; 969
23 Masuda Y, Ishida N, Murakami M. Eur. J. Org. Chem. 2016; 5822

24a Dewanji A, Krach PE, Rueping M. Angew. Chem. Int. Ed. 2019; 58: 3566
24b Shen Y, Gu Y, Martin R. J. Am. Chem. Soc. 2018; 140: 12200
24c Zhang L, Si X, Yang Y, Zimmer M, Witzel S, Sekine K, Rudolph M, Hashmi AS. K. Angew. Chem. Int. Ed. 2019; 58: 1823
24d Si X, Zhang L, Hashmi AS. K. Org. Lett. 2019; 21: 6329

25a Ishida N, Masuda Y, Uemoto S, Murakami M. Chem. Eur. J. 2016; 22: 6524
25b Ishida N, Masuda Y, Imamura Y, Yamazaki K, Murakami M. J. Am. Chem. Soc. 2019; 141: 19611

26a Masuda Y, Ishida N, Murakami M. Chem. Asian J. 2019; 14: 403
26b Krach PE, Dewanji A, Yuan T, Rueping M. Chem. Commun. 2020; 56: 6082

27 Abadie B, Jardel D, Pozzi G, Toullec P, Vincent J.-M. Chem. Eur. J. 2019; 25: 16120
28 Li Y, Lei M, Gong L. Nat. Catal. 2019; 2: 1016
29 Schirmer TE, Wimmer A, Weinzierl FW. C, König B. Chem. Commun. 2019; 55: 10796
30 Zhu D.-L, Li H.-X, Xu Z.-M, Li H.-Y, Young DJ, Lang J.-P. Org. Chem. Front. 2019; 6: 2353
31 Ding W, Lu L.-Q, Zhou Q.-Q, Wei Y, Chen J.-R, Xiao W.-J. J. Am. Chem. Soc. 2017; 139: 63
32 Michelet B, Deldaele C, Kajouj S, Moucheron C, Evano G. Org. Lett. 2017; 19: 3576

33a Börjesson M, Moragas T, Martin R. J. Am. Chem. Soc. 2016; 138: 7504
33b Terrett JA, Cuthbertson JD, Shurtleff VW, MacMillan DW. C. Nature 2015; 524: 330

34a Perry IB, Brewer TF, Sarver PJ, Schultz DM, DiRocco DA, MacMillan DW. C. Nature 2018; 560: 70
34b Bosset C, Beucher H, Bretel G, Pasquier E, Queguiner L, Henry C, Vos A, Edwards JP, Meerpoel L, Berthelot D. Org. Lett. 2018; 20: 6003
34c Zhu X, Xie X, Li P, Guo J, Wang L. Org. Lett. 2016; 18: 1546
34d Liu D, Liu C, Li H, Lei A. Angew. Chem. Int. Ed. 2013; 52: 4453

35a Nakajima K, Miyake Y, Nishibayashi Y. Acc. Chem. Res. 2016; 49: 1946
35b Gu Q.-S, Li Z.-L, Liu X.-Y. Acc. Chem. Res. 2020; 53: 170
35c Hu A, Guo J.-J, Pan H, Zuo Z. Science 2018; 361: 668
35d Chu JC. K, Rovis T. Angew. Chem. Int. Ed. 2018; 57: 62
35e Yang Y, Huang H, Zhang X, Zeng W, Liang Y. Synthesis 2013; 45: 3137

36 Shaw MH, Shurtleff VW, Terrett JA, Cuthbertson JD, MacMillan DW. C. Science 2016; 352: 1304

37a Heitz DR, Tellis JC, Molander GA. J. Am. Chem. Soc. 2016; 138: 12715
37b Shields BJ, Doyle AG. J. Am. Chem. Soc. 2016; 138: 12719

38 Huang L, Rueping M. Angew. Chem. Int. Ed. 2018; 57: 10333
39 Xue X.-S, Ji P, Zhou B, Cheng J.-P. Chem. Rev. 2017; 117: 8622

40a Masuda Y, Ishida N, Murakami M. J. Am. Chem. Soc. 2015; 137: 14063

See also:

40b Gui Y.-Y, Zhou W.-J, Ye J.-H, Yu D.-G. ChemSusChem 2017; 10: 1337

41a Rajamalli P, Senthilkumar N, Gandeepan P, Ren-Wu C.-Z, Lin H.-W, Cheng C.-H. J. Mater. Chem. C 2016; 4: 900
41b Neveselý T, Svobodová E, Chudoba J, Sikorski M, Cibulka R. Adv. Synth. Catal. 2016; 358: 1654