Ground- and Excited-State Quinones: Perspectives in Organocatalysis and 
Visible-Light Photocatalysis

Stephanie Lerch; Lisa-Natascha Unkel; Patrick Wienefeld; Malte Brasholz

doi:10.1055/s-0034-1379363

Synlett, Table of Contents

Synlett 2014; 25(19): 2673-2680
DOI: 10.1055/s-0034-1379363

synpacts

Ground- and Excited-State Quinones: Perspectives in Organocatalysis and Visible-Light Photocatalysis

Authors

Stephanie Lerch

University of Hamburg, Department of Chemistry, Institute of Organic Chemistry, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany Email: malte.brasholz@chemie.uni-hamburg.de
Lisa-Natascha Unkel

University of Hamburg, Department of Chemistry, Institute of Organic Chemistry, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany Email: malte.brasholz@chemie.uni-hamburg.de
Patrick Wienefeld

University of Hamburg, Department of Chemistry, Institute of Organic Chemistry, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany Email: malte.brasholz@chemie.uni-hamburg.de
Malte Brasholz*

University of Hamburg, Department of Chemistry, Institute of Organic Chemistry, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany Email: malte.brasholz@chemie.uni-hamburg.de

Abstract

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Abstract

Quinone organocatalysis is an emerging area, and this report highlights some recently developed thermal and photocatalytic reactions, with particular emphasis on photooxygenation reactions. Further, it is discussed how the orthogonal ground- and excited-state reactivities of quinones can be utilized for the development of tandem catalytic processes.

Key words

quinones - organocatalysis - photochemistry - photooxidations - tandem reactions

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References

References
1 The Chemistry of Quinonoid Compounds . Patai S, Rappaport Z. Wiley; New York: 1988

For reviews on quinone photochemistry, see:

2a Görner H In CRC Handbook of Organic Photochemistry and Photobiology . Vol. 1. Griesbeck A, Oelgemöller M, Ghetti F. CRC Press; Boca Raton: 2012. 3rd ed., 683
2b Mukherjee T. PINSA-A: Proc. Indian Natl. Sci. Acad., Part A 2000; 66: 239

For reviews, see:

3a Walker D, Hiebert JD. Chem. Rev. 1967; 67: 153
3b Buckle DR In Encyclopedia of Reagents for Organic Synthesis . Vol. 3. Paquette LA. Wiley; Chichester: 1995: 1699
3c Bharate SB. Synlett 2006; 496

4 Miyamura H, Shiramizu M, Matsubara R, Kobayashi S. Angew. Chem. Int. Ed. 2008; 47: 8093 ; Angew. Chem. 2008, 120, 8213
5 Chandrasekhar S, Sumithra G, Yadav JS. Tetrahedron Lett. 1996; 37: 1645

6a Sharma GV. M, Lavanya B, Mahalingam AK, Krisha PR. Tetrahedron Lett. 2000; 41: 10323
6b Cosner CC, Cabrera PJ, Byrd KM, Adams Thomas AM, Helquist P. Org. Lett. 2011; 13: 2071

7 Liu L, Floreancing P. Org. Lett. 2010; 12: 4686
8 Zhang W, Ma H, Zhou L, Sun Z, Du Z, Miao H, Xu J. Molecules 2008; 13: 3236
9 Shen Z, Dai J, Xiong J, He X, Mo W, Hu B, Sun N, Hu X. Adv. Synth. Catal. 2011; 353: 3031
10 Mure M, Mills SA, Klinman JP. Biochemistry 2002; 41: 9269

11a Mure M. Acc. Chem. Res. 2004; 37: 131
11b Largeron M, Fleury M.-B. Science 2013; 339: 43

12 Wendlandt AE, Stahl SS. Org. Lett. 2012; 14: 2850
13 Lerch S, Unkel L.-N, Brasholz M. Angew. Chem. Int. Ed. 2014; 53: 6558 , Angew. Chem. 2014, 126, 6676
14 Imm S, Bähn S, Tillack A, Mevius K, Neubert L, Beller M. Chem. Eur. J. 2010; 16: 2705
15 Siddiki SM. A. H, Kon K, Shimizu K. Chem. Eur. J. 2013; 19: 14416

16a Mech J, Grela MA, Szaciłowski K. Dyes Pigm. 2014; 103: 202
16b Rath MC, Pal H, Mukherjee T. Radiat. Phys. Chem. 1996; 47: 221
16c Fagnoni M, Dondi D, Ravelli D, Albini A. Chem. Rev. 2007; 107: 2725
16d Hamonue K, Kajiwara Y, Miyake T, Nakayama T, Hirase S, Teranishi H. Chem. Phys. Lett. 1983; 94: 276
16e Anouar EH, Osman CP, Weber J.-FF, Ismail NH. Springerplus 2014; 3: 233
16f Ritter J, Borst H.-U, Lindner T, Hauser M, Brosig S, Bredereck K, Steiner UE, Kühn D, Kelemen J, Kramer HE. A. J. Photochem. Photobiol., A 1988; 41: 227
16g Ravelli D, Fagnoni M. ChemCatChem 2012; 4: 169
16h Neumann M, Füldner S, König B, Zeitler K. Angew. Chem. Int. Ed. 2011; 50: 951 ; Angew. Chem. 2011, 123, 981

17a Advances in Electron Transfer Chemistry . Vol. 5. Mariano PS. JAI Press; London: 1996
17b Mella M, Fagnoni M, Freccero M, Fasani E, Albini A. Chem. Soc. Rev. 1998; 27: 81
17c Electron Transfer in Chemistry . Balzani V. Wiley-VCH; Weinheim: 2001

18a Rehm D, Weller A. Ber. Bunsen-Ges. 1969; 73: 834
18b Rehm D, Weller A. Isr. J. Chem. 1970; 8: 259
18c Weller A. Pure Appl. Chem. 1982; 54: 1885

19 Ohkubo K, Fujimoto A, Fukuzumi S. J. Am. Chem. Soc. 2013; 135: 5368

20a Cui L, Matsusaki Y, Tada N, Miura T, Uno B, Itoh A. Adv. Synth. Catal. 2013; 355: 2203
20b Yamaguchi T, Nobuta T, Tada N, Miura T, Nakayama T, Uno B, Itoh A. Synlett 2014; 25: 1453
20c Tachikawa Y, Cui L, Matsusaki Y, Tada N, Miura T, Itoh A. Tetrahedron Lett. 2013; 54: 6218
20d Shimada Y, Hattori K, Tada N, Miura T, Itoh A. Synthesis 2013; 45: 2684
20e Cui L, Tada N, Okubo H, Miura T, Itoh A. Green Chem. 2011; 13: 2347

21 Campos-Martin JM, Blanco-Brieva G, Fierro JL. G. Angew. Chem. Int. Ed. 2006; 45: 6962 ; Angew. Chem. 2006, 118, 7116
22 Gollnick K, Held S, Mártire DO, Braslavsky SE. J. Photochem. Photobiol., A 1992; 69: 155
23 Byteva IM, Gurinovich GP, Golomb OL, Karpov VV. Zh. Prikl. Spektrosk. 1986; 44: 589
24 Gottschalk P, Paczkowski J, Neckers DC. J. Photochem. 1986; 35: 277
25 Bhattacharyya K, Das PK. Chem. Phys. Lett. 1985; 116: 326

26a Fogg DE, dos Santos EN. Coord. Chem. Rev. 2004; 248: 2365
26b Ajamian A, Gleason JL. Angew. Chem. Int. Ed. 2004; 43: 3754 ; Angew. Chem. 2004, 116, 3842

27 Movassaghi M, Schmidt MA, Ashenhurst JA. Org. Lett. 2008; 10: 4009
28 Barckholtz C, Barckholtz TA, Hadad CM. J. Am. Chem. Soc. 1999; 12: 491
29 Sanderson RT. Chemical Bonds and Bond Energy . Academic Press; New York: 1976
30 The proposed mechanism was supported by control experiments in the absence of an anthraquinone catalyst; see ref. 13.