Microphotochemistry Using 5-mm Light-Emitting Diodes: Energy-Efficient Photooxidations

Abstract

Commercial, inexpensive 5-mm milliwatt light-emitting diodes are effective sources for batch microphotochemical oxidations. Using limited quantities of singlet oxygen, these oxidations are atom economical and therefore useful for labeling experiments with rare isotopes.

Key words

photooxidation - arenes - peroxides - photoreactors - light-emitting diodes

• References

• 1 Hudlicky M. Oxidations in Organic Chemistry . American Chemical Society; Washington D.C.: 1990
• 2 Bowden K, Heibron IM, Jones ER. H, Weedon BC. L. J. Chem. Soc. 1946; 39
• 3 Corey EJ, Schmidt G. Tetrahedron Lett. 1979; 399
• 4 For example, see: Krapcho AP, Larson JR, Eldridge JM. J. Org. Chem. 1977; 42: 3749
• 5a Arterburn JB. Tetrahedron 2001; 57: 9765
• 5b Kowalski P, Mitka K, Ossowska K, Kolarska Z. Tetrahedron 2005; 61: 1933
• 6 Arends IW. C. E, Sheldon RA In Modern Oxidation Methods . 2nd ed. Baeckvall J.-E. Wiley-VCH; Weinheim: 2010: 147
• 7 Johnson RA, Sharpless KB In Catalytic Asymmetric Synthesis . 2nd ed. Ojima I. Wiley-VCH; New York: 2000: 357
• 8a Chatgilialoglu C, Crich D, Komatsu M, Ryu I. Chem. Rev. 1999; 99: 1991
• 8b Larkin DR. J. Org. Chem. 1990; 55: 1563
• 9a Di Tommaso S, Rotureau P, Crescenzi O, Adamo C. Phys. Chem. Chem. Phys. 2011; 13: 14636

See also:
• 9b Hoover JM, Stahl SS. J. Am. Chem. Soc. 2011; 133: 1691
• 9c Esteruelas MA, García-Obregón T, Herrero J, Oliván M. Organometallics 2011; 30: 6402
• 10 Ricci M, Bianchi D, Bortolo R In Sustainable Industrial Processes . Caani F, Centi G, Perathoner S, Trifirò F. Wiley-VCH; Weinheim: 2009: 507
• 11a Khan AU. J. Phys. Chem. 1976; 80: 1976
• 11b Greer A. Acc. Chem. Res. 2006; 39: 797
• 11c Clennan EL, Pace A. Tetrahedron 2005; 61: 6665
• 11d Ogilby PR. Chem. Soc. Rev. 2010; 39: 3181
• 12 Zamadar M, Greer A In Handbook of Synthetic Photochemistry . Albini A, Fagnoni M. Wiley-VCH; Weinheim: 2010: 353
• 13a Turro NJ, Ramaurthy V, Scaiano JC. Modern Molecular Photochemistry of Organic Molecules . University Science Books; Sausalito: 2010: 1001
• 13b Anslyn EV, Dougherty DA. Modern Physical Organic Chemistry . University Science Books; Sausalito: 2006: 989
• 13c DeRosa MC, Crutchley RJ. Coord. Chem. Rev. 2002; 233: 351
• 13d Wasserman HH, Ives JL. Tetrahedron 1981; 37: 1825
• 13e Sasaoka M, Hart H. J. Org. Chem. 1979; 44: 368
• 13f Adam W, Bosio S, Bartoschek A, Griesbeck AG In CRC Handbook of Organic Photochemistry and Photobiology . 2nd ed. Horspool W, Lenci F. CRC Press; Boca Raton: 2004: Chap. 25
• 14a Bartlett PD, Schaap AP. J. Am. Chem. Soc. 1970; 92: 3223
• 14b Adam W, Trofimov AV In Patai’s Chemistry of Functional Groups [Online] . Wiley; New York: 2009. DOI: 10.1002/9780470682531.pat0361
• 15a Schenck GO. Naturwissenschaften 1948; 35: 28
• 15b Frimer AA. Chem. Rev. 1979; 79: 359
• 16a Kahn AU, Kasha M. J. Chem. Phys. 1963; 39: 2105
• 16b Held AM, Halko DJ, Hurst JK. J. Am. Chem. Soc. 1978; 100: 5732
• 17 Aubry JM. J. Am. Chem. Soc. 1985; 107: 5844
• 18 Pierlot C, Nardello V, Schrive J, Mabille C, Barbillat J, Sombret B, Aubry JM. J. Org. Chem. 2002; 67: 2418
• 19 Murray RW, Kaplan ML. J. Am. Chem. Soc. 1969; 91: 5358
• 20a Catir M, Kilic H. Synlett 2003; 1180
• 20b Catir M, Kilic H, Nardello-Rataj V, Aubry JM, Kazaz C. J. Org. Chem. 2009; 74: 4560
• 21 Adam W, Kazakov DV, Kazakov VP, Kiefer W, Latypova RR, Schluecker S. Photochem. Photobiol. Sci. 2004; 3: 182
• 22a Lancaster JR, Marti AA, López-Gejo J, Jockusch S, O’Conner N, Turro NJ. Org. Lett. 2008; 10: 5509
• 22b Aubry JM, Pierlot C, Rigaudy J, Schmidt R. Acc. Chem. Res. 2003; 36: 668
• 22c Martinez GR, Ravanat JL, Medeiros MH. G, Cadet J, Di Mascio P. J. Am. Chem. Soc. 2000; 122: 10212
• 22d Rickborn B. Org. React. 1998; 53: 223
• 22e Saito I, Nagata R, Matsuura T. J. Am. Chem. Soc. 1985; 107: 6329
• 23 Hang J, Ghorai P, Finkenstaedt-Quinn SA, Findik I, Sliz E, Kuwata KT, Dussault PH. J. Org. Chem. 2012; 77: 1233
• 24 Anquez F, Yazidi-Belkoura IE, Randoux S, Suret P, Courtade E. Photochem. Photobiol. 2012; 88: 167
• 25a Schweitzer C, Schmidt R. Chem. Rev. 2003; 103: 1685
• 25b Tuite EM, Kelly JM. J. Photochem. Photobiol. B 1993; 21: 103
• 25c Tanielian C, Wolff C. J. Phys. Chem. 1995; 99: 9825
• 25d Lamberts JJ. M, Schumacher DR, Neckers DC. J. Am. Chem. Soc. 1984; 106: 5879
• 25e Guarini A, Tundo P. J. Org. Chem. 1987; 52: 3501
• 26a Eberhardt MK. Reactive Oxygen Metabolites . CRC Press; Boca Raton: 2001
• 26b Agnez-Lima LF, Melo JT. A, Silva AE, Oliveira AH. S, Timoteo AR. S, Lima-Bessa KM, Martinez GR, Medeiros MH. G, Di Mascio P, Galhardo RS, Menck CF. M. Mutat. Res., Rev. Mutat. Res. 2012; in press; http://dx.doi.org/10.1016/j.mrrev.2011.12.005
• 27a Kanofsky JR. Chem. Biol. Interact. 1989; 70: 1
• 27b Ronsein GE, Oliveira CB, Miyamoto S, Medeiros MH. G, Di Mascio P. Chem. Res. Toxicol. 2008; 21: 1271
• 28a Sun S, Bao Z, Ma H, Zhang D, Zheng X. Biochemistry 2007; 46: 6668
• 28b Uemi M, Ronsein GE, Prado FM, Motta FD, Miyamoto S, Medeiros MH. G, Di Mascio P. Chem. Res. Toxicol. 2011; 24: 887
• 29 Krieger-Liszkay A. J. Exp. Bot. 2005; 56: 337
• 30a Flors C, Nonell S. Acc. Chem. Res. 2006; 39: 293
• 30b Triantaphylidès C, Havaux M. Trends Plant Sci. 2009; 14: 291
• 31a Lledias F, Rangel P, Hansberg W. Free Radical Biol. Med. 1999; 26: 1396
• 31b Aguirre J, Ríos-Momberg M, Hewitt D, Hansberg W. Trends Microbiol. 2005; 13: 111
• 32a Dougherty TJ, Gomer CJ, Henderson BW, Jori G, Kessel D, Korbelik M, Moan J, Peng Q. J. Natl. Cancer Inst. 1998; 90: 889
• 32b Celli JP, Spring BQ, Rizvi I, Evens CL, Pogue BW, Hasan T. Chem. Rev. 2010; 110: 2795
• 33 Boykin DW. ¹⁷O NMR Spectroscopy in Organic Chemistry . CRC Press; Boca Raton: 1991
• 34 A preliminary report has appeared; see: Carney JM, Hammer RJ, Hulce M, Lomas CM, Miyashiro D. Tetrahedron Lett. 2011; 52: 352

• For examples using isotopically labeled ¹O₂, see:

• 35a Turro NJ, Chow MF, Rigaudy J. J. Am. Chem. Soc. 1981; 103: 7218
• 35b Turro NJ, Chow MF. J. Am. Chem. Soc. 1980; 102: 1191
• 35c Braun AM, Dahn H, Gassmann E, Gerothanassis I, Jakob L, Kateva J, Martinez CG, Ollveros E. Photochem. Photobiol. 1999; 70: 868
• 36a Tise FP, Kropp PJ. Org. Synth. Coll. Vol. VII . John Wiley & Sons; London: 1990: 304
• 36b Cargill RL, Dalton JR, Morton GH, Caldwell WE. Org. Synth. Coll. Vol. VII . John Wiley & Sons; London: 1990: 315
• 36c Okabe M. Org. Synth. Coll. Vol. X . John Wiley & Sons; London: 2004: 718
• 37 Moradei OM, Paquette LA. Org. Synth. Coll. Vol. XI . John Wiley & Sons; London: 2009: 128
• 38 For example, over 5 minutes the highly energy-efficient Osram sodium spectral lamp causes a 4–5 °C increase in temperature, measured 1 cm from the lamp housing
• 39 Ciana CL, Bochet CG. Chimia 2007; 61: 650
• 40a Hashimoto MC. E, Toffoli DJ, Prates RA, Courrol LC, Ribeiro MS. Proc. SPIE Int. Soc. Opt. Eng. 2009; 7380: 73803F-1
• 40b Konopka K, Goslinski T. J. Dent. Res. 2007; 86: 694
• 40c Pervais S, Olivio M. Clin. Exp. Pharmacol. Physiol. 2006; 33: 551
• 40d Schmidt MH, Meyer GA, Reichert KW, Cheng J, Krouwer HG, Ozker K, Whelan HT. J. Neurooncol. 2004; 67: 201
• 40e Kamano H, Okamoto K, Sakata I, Kubota Y, Tanaka T. Transplant. Proc. 2000; 32: 2442
• 40f Schmidt MH, Bajic DM, Reichert KW, Martin TS, Meyer GA, Whelan HT. Neurosurgery 1996; 38: 552
• 41a Yin S, Liu B, Zhang P, Morikawa T, Yamanaka K, Sato T. J. Phys. Chem. C 2008; 112: 12425
• 41b Bourne RA, Han X, Poliakoff M, George MW. Angew. Chem. Int. Ed. 2009; 48: 5322
• 41c Bonacin JA, Engelmann FM, Severino D, Toma HE, Baptista MS. J. Braz. Chem. Soc. 2009; 20: 31
• 41d Carofiglio T, Donnola P, Maggini M, Rossetto M, Rossi E. Adv. Synth. Catal. 2008; 350: 2815
• 41e Lapkin AA, Boddu VM, Aliev GN, Goller B, Polisski S, Kovalev D. Chem. Eng. J. 2008; 136: 321
• 41f Meyer S, Tietze D, Rau S, Schäfer B, Kreisel G. J. Photochem. Photobiol. A 2007; 186: 248
• 41g Kreisel G, Meyer S, Tietze D, Fidler T, Gorges R, Kirsch A, Schäfer B, Rau S. Chem. Ing. Tech. 2007; 79: 153
• 41h Chen DH, Ye X, Li K. Chem. Eng. Technol. 2005; 28: 95
• 42 Oelgemöller M, Shvydkiv O. Molecules 2011; 16: 7522
• 43a Schmidt R, Schaffner K, Trost W, Brauer HD. J. Phys. Chem. 1984; 88: 956
• 43b Motoyoshiya J, Masunaga T, Harumoto D, Ishiguro S, Narita S, Hayashi S. Bull. Chem. Soc. Jpn. 1993; 66: 1166
• 43c Wu KC, Trozzolo AM. J. Phys. Chem. 1979; 83: 3180
• 44a Graziano ML, Iesce MR, Carli B, Scarpati R. Synthesis 1983; 125
• 44b Lutz RE, Welstead WJ. Jr, Bass RG, Dale JI. J. Org. Chem. 1962; 27: 1111
• 44c Haynes RK, Peters JM, Wilmot ID. Aust. J. Chem. 1980; 33: 2653
• 45 Morita Y, Tokuyama H, Fukuyama T. Org. Lett. 2005; 7: 4337
• 46a Greenfield S, Mackenzie K. J. Chem. Soc., Perkin Trans. 2 1986; 1651
• 46b Wender PA, Paxton TJ, Williams TJ. J. Am. Chem. Soc. 2006; 128: 14814
• 47 Allen CF. H, VanAllan JA. J. Am. Chem. Soc. 1950; 72: 5165
• 48a Boekelheide V, Goldman M. J. Org. Chem. 1954; 19: 575
• 48b Luo H, Zeng Q, Wei Y, Li B, Wang F. Synth. Commun. 2004; 34: 2269
• 49 Kamikawa T, Morimoto J. US Patent 7122711 B2, 2006
• 50 Johnson JR, Grummitt O. Org. Synth. Coll. Vol. III . John Wiley & Sons; London: 1955: 806
• 51a Ceylan M, Gürdere MB, Burdak Y, Kazaz C, Seçen H. Synthesis 2004; 1750
• 51b Amarnath V, Amarnath K. J. Org. Chem. 1995; 60: 301
• 52 Eisenthal KB, Turro NJ, DuPuy CG, Hrovat DA, Jenny TA. J. Phys. Chem. 1986; 90: 5168
• 53a Donkers RL, Workentin MS. J. Am. Chem. Soc. 2004; 126: 1688
• 53b Wasserman HH, Scheffer JR, Cooper JL. J. Am. Chem. Soc. 1972; 94: 4991
• 54a Kotani H, Ohkubo K, Fukuzumi S. J. Am. Chem. Soc. 2004; 126: 1599
• 54b Duerr BF, Chung YS, Czarnik AW. J. Org. Chem. 1988; 53: 2120
• 55 Wasserman HH, Wiberg KB, Larsen DL, Parr J. J. Org. Chem. 2005; 70: 105
• 56 Fuchter MJ, Hoffman BM, Barrett AG. M. J. Org. Chem. 2006; 71: 724
• 57 Bikales NM, Becker EI. J. Org. Chem. 1956; 21: 1405
• 58 Yates P, Stout GH. J. Am. Chem. Soc. 1954; 76: 5110