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Muniz, K.: 2018 Science of Synthesis, 2017/4: Catalytic Oxidation in Organic Synthesis DOI: 10.1055/sos-SD-225-00002
Catalytic Oxidation in Organic Synthesis

2.1 Photocatalytic Oxidation

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Herausgeber: Muniz, K.

Autoren: Andries-Ulmer, A.; Bellina, F.; Berkessel, A.; Borrell, M.; Caballero, A.; Calleja, P.; Chemler, S.; Chen, P.; Costas, M.; Díaz-Requejo, M. M.; Dorel, R.; Dornan, L.; Ebner, D.; Echavarren, A. M.; Engler, H.; Esguerra, K.; Farràs, P.; Funes, I.; Garrido, P.; Gimbert-Suriñach, C.; Gómez-Arrayas, R.; Griesbeck, A. G. ; Gulder, T.; Hughes, N.; Ikariya, T.; Ishihara, K. ; Jiao, N.; Kayaki, Y. ; Kleczka, M.; Leuther, T.; Li, Z.; Liu, G.; Llobet, A.; Lumb, J.-P.; Martínez, C.; Maseras, F. ; Muldoon, M.; Muniz, K.; Park, N.; Patel, H.; Perego, L.; Pérez, P.; Race, N.; Rodríguez, Nú.; Sigman, M. S.; Sillner, S.; Singh, F. V. ; Stoltz, B. ; Uyanik, M. ; Vicens, L.; Wdowik, T.; Wirth, T.; Wright, A.

Titel: Catalytic Oxidation in Organic Synthesis

Print ISBN: 9783132012318; Online ISBN: 9783132403710; Buch-DOI: 10.1055/b-003-129345

1st edition © 2018. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie

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Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Reihenherausgeber: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Koch, G.; Molander, G. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Typ: Mehrbändiges Werk

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Abstract

In this chapter, the transfer of molecular oxygen to organic substrates initiated by the action of an electronically excited catalyst with a substrate molecule or with triplet oxygen is described. Most of the primary products that derive from these reactions have an intact oxygen–oxygen bond (i.e., they are peroxides, hydroperoxides, or acyclic/cyclic dialkyl peroxides) or they are, in subsequent steps, converted into reduced products such as alcohols, ethers, or carbonyl compounds.

Schlüsselwörter

alkenes - allylic alcohols - catalysts - hydroperoxides - oxygenation - peroxides - photochemistry - photooxidation - porphyrins
 
  • 1 The Chemistry of Peroxides. Rappoport Z. Wiley; Chichester, UK 2006
    Google Scholar
  • 2 The Chemistry of Peroxides. Patai S. Wiley; Chichester, UK 1983
    Google Scholar
  • 3 Active Oxygen in Chemistry. Foote C S, Valentine J S, Greenberg A, Liebman J F. Blackie; London 1995
    Google Scholar
  • 5 Advances in Oxygenated Processes. Baumstark A L. Jai; Greenwich, CT 1988
    Google Scholar
  • 6 CRC Handbook of Organic Photochemistry and Photobiology, 3rd ed.,. Griesbeck A G, Oelgemöller M, Ghetti F. CRC; Boca Raton, FL 2012
    Google Scholar
  • 7 Ravelli D, Fagnoni M. ChemCatChem 2012; 4: 169
  • 8 Xuan J, Xiao W-J. Angew. Chem. Int. Ed. 2012; 51: 6828
  • 9 Ravelli D, Fagnoni M, Albini A. Chem. Soc. Rev. 2013; 42: 97
  • 10 Ravelli D, Protti S, Fagnoni M. Chem. Rev. 2016; 116: 9850
  • 11 Kranz D P, Griesbeck A G, Alle R, Perez-Ruiz R, Neudörfl J M, Meerholz K, Schmalz H-G. Angew. Chem. Int. Ed. 2012; 51: 6000
  • 12 Gambarotti C, Melone L, Caronna T, Punta C. Curr. Org. Chem. 2013; 17: 2406
  • 13 Reckenthäler M, Griesbeck A G. Adv. Synth. Catal. 2013; 355: 2727
  • 14 Lu H, Yao J. Curr. Org. Chem. 2014; 18: 1365
  • 15 Fukuzumi S, Ohkubo K. Org. Biomol. Chem. 2014; 12: 6059
  • 16 Fukuzumi S, Ohkubo K. Chem. Sci. 2013; 4: 561
  • 17 Radicals in Organic Synthesis. Renaud P, Sibi M P. Wiley-VCH; Weinheim, Germany 2008
    Google Scholar
  • 18 Linker T, Schmittel M. Radikale und Radikalionen in der Organischen Synthese. Wiley-VCH; Weinheim, Germany 1998
    Google Scholar
  • 19 Sun X, Li X, Song S, Zhu Y, Liang Y-F, Jiao N. J. Am. Chem. Soc. 2015; 137: 6059
  • 20 Griesbeck A G, Steinwascher J, Reckenthäler M, Uhlig J. Res. Chem. Intermed. 2013; 39: 33
  • 21 Griesbeck A G, Reckenthäler M, Uhlig J. Photochem. Photobiol. Sci. 2010; 9: 775
  • 22 Yadav A K, Yadav L D S. Green Chem. 2015; 17: 3515
  • 23 Fan W, Yang Q, Xu F, Li P. J. Org. Chem. 2014; 79: 10588
  • 24 Ohkubo K, Hirose K, Fukuzumi S. Photochem. Photobiol. Sci. 2016; 15: 731
  • 25 Ohkubo K, Fujimoto A, Fukuzumi S. Chem. Commun. (Cambridge) 2011; 47: 8515
  • 26 Kalaitzakis D, Triantafyllakis M, Sofiadis M, Noutsias D, Vassilikogiannakis G. Angew. Chem. Int. Ed. 2016; 55: 4605
  • 27 Kalaitzakis D, Kouridaki A, Noutsias D, Montagnon T, Vassilikogiannakis G. Angew. Chem. Int. Ed. 2015; 54: 6283
  • 28 Miyashi T, Konno A, Takahashi Y. J. Am. Chem. Soc. 1988; 110: 3676
  • 29 Griesbeck A G, Sadlek O, Gollnick K, Polborn K. Angew. Chem. Int. Ed. Engl. 1994; 33: 2300
  • 30 Kamata M, Ohta M, Komatsu K-i, Kim H-S, Wataya Y. Tetrahedron Lett. 2002; 43: 2063
  • 31 Griesbeck A G, Sadlek O, Polborn K. Liebigs Ann. 1996; 545
  • 32 Parrish J D, Ischay M A, Lu Z, Guo S, Peters N R, Yoon T P. Org. Lett. 2012; 14: 1640
  • 33 Gesmundo N J, Nicewicz D A. Beilstein J. Org. Chem. 2014; 10: 1272
  • 34 Adam W, Grabowski S, Wilson R M. Acc. Chem. Res. 1990; 23: 165
  • 35 Anderson M A, Grissom C B. J. Am. Chem. Soc. 1995; 117: 5041
  • 36 Adam W, Hannemann K, Wilson R M. J. Am. Chem. Soc. 1984; 106: 7646
  • 37 Adam W, Hannemann K, Wilson R M. J. Am. Chem. Soc. 1986; 108: 929
  • 38 Adam W, Kliem U, Mosandl T, Peters E-M, Peters K, von Schnering H G. J. Org. Chem. 1988; 53: 4986
  • 39 Mischne M P, Huber S N, Zinczuk J. Can. J. Chem. 1999; 77: 237
  • 40 Diaz-Uribe C E, Daza M C, Martínez F, Páez-Mozo E A, Guedes C L B, Di Mauro E. J. Photochem. Photobiol. A 2010; 215: 172
  • 41 Zou Y-Q, Chen J-R, Liu X-P, Lu L-Q, Davis R L, Jørgensen K A, Xiao W-J. Angew. Chem. Int. Ed. 2012; 51: 784
  • 42 Xuan J, Xiao W-J. Angew. Chem. Int. Ed. 2012; 51: 6828
  • 43 Pitre S P, McTiernan C D, Ismaili H, Scaiano J C. J. Am. Chem. Soc. 2013; 135: 13286
  • 44 Nicewicz D A, Nguyen T M. ACS Catal. 2014; 4: 355
  • 45 Toyao T, Ueno N, Miyahara K, Matsui Y, Kim T-H, Horiuchi Y, Ikeda H, Matsuoka M. Chem. Commun. (Cambridge) 2015; 51: 16103
  • 46 Johnson J A, Luo J, Zhang X, Chen Y-S, Morton M D, Echeverría E, Torres F E, Zhang J. ACS Catal. 2015; 5: 5283
  • 47 Luo J, Zhang X, Zhang J. ACS Catal. 2015; 5: 2250
  • 48 Yi H, Bian C, Hu X, Niu L, Lei A. Chem. Commun. (Cambridge) 2015; 51: 14046
  • 49 Ohkubo K, Mizushima K, Iwata R, Souma K, Suzuki N, Fukuzumi S. Chem. Commun. (Cambridge) 2010; 46: 601
  • 50 Yamada Y, Maeda K, Ohkubo K, Karlin K D, Fukuzumi S. Phys. Chem. Chem. Phys. 2012; 14: 9654
  • 51 Santamaria J, Jroundi R, Rigaudy J. Tetrahedron Lett. 1989; 30: 4677
  • 52 Santamaria J, Jroundi R. Tetrahedron Lett. 1991; 32: 4291
  • 53 Fujita M, Ishida A, Takamuku S, Fukuzumi S. J. Am. Chem. Soc. 1996; 118: 8566
  • 54 Maslak P, Chapman Jr. W H. Tetrahedron 1990; 46: 2715
  • 55 Mattes S L, Farid S. J. Am. Chem. Soc. 1982; 104: 1454
  • 56 Gollnick K, Schnatterer A. Tetrahedron Lett. 1985; 26: 173
  • 57 Gollnick K, Schnatterer A. Tetrahedron Lett. 1985; 26: 5029
  • 58 Eriksen J, Foote C S, Parker T L. J. Am. Chem. Soc. 1977; 99: 6455
  • 59 Eriksen J, Foote C S. J. Am. Chem. Soc. 1980; 102: 6083
  • 60 Ohkubo K, Nanjo T, Fukuzumi S. Catal. Today 2006; 117: 356
  • 61 Ohkubo K, Nanjo T, Fukuzumi S. Org. Lett. 2005; 7: 4265
  • 62 Kotani H, Ohkubo K, Fukuzumi S. J. Am. Chem. Soc. 2004; 126: 15999
  • 63 Fukuzumi S, Ohkubo K. Org. Biomol. Chem. 2014; 12: 6059
  • 64 Singlet Oxygen: Applications in Biosciences and Nanosciences. Nonell S, Flors C. RSC; Cambridge, UK 2016
    Google Scholar
  • 65 Wasserman H H, DeSimone R W, Chia K R X, Banwell M G. e-EROS Encyclopedia of Reagents for Organic Synthesis. Wiley; Chichester, UK (2001); DOI: 10.1002/047 084 289X.rs035.
    Google Scholar
  • 66 Singlet Oxygen. Wasserman H H, Murray R W. Academic; New York 1979
    Google Scholar
  • 67 Pierlot C, Nardello V, Schrive J, Mabille C, Barbillat J, Sombret B, Aubry J-M. J. Org. Chem. 2002; 67: 2418
  • 68 Bartlett P D, Mendenhall G D, Durham D L. J. Org. Chem. 1980; 45: 4269
  • 69 Aubry J M, Cazin B, Duprat F. J. Org. Chem. 1989; 54: 726
  • 70 Kuwajima I, Urabe H. Tetrahedron Lett. 1981; 22: 5191
  • 71 Evans D F, Upton M W. J. Chem. Soc., Dalton Trans. 1985; 1151
  • 72 Martinez G R, Ravanat J-L, Medeiros M H G, Cadet J, Di Mascio P. J. Am. Chem. Soc. 2000; 122: 10212
  • 73 Schmidt R. Photochem. Photobiol. 2006; 82: 1161
  • 74 Schweitzer C, Schmidt R. Chem. Rev. 2003; 103: 1685
  • 75 Wilkinson F, Helman W P, Ross A B. J. Phys. Chem. Ref. Data 1995; 24: 663
  • 76 Jiang X-D, Xi D, Le Guennic B, Guan J, Jacquemin D, Guan J, Xiao L-J. Tetrahedron 2015; 71: 7676
  • 77 Ghogare A A, Greer A. Chem. Rev. 2016; 116: 9994
  • 78 Griesbeck A G, Sillner S, Kleczka M, In Singlet Oxygen: Applications in Biosciences and Nanosciences. Nonell S, Flors C. RSC; Cambridge, UK 2016. Vol.  1, p  369.
    Google Scholar
  • 79 Schenck G O, Eggert H, Denk W. Justus Liebigs Ann. Chem. 1953; 584: 177
  • 80 Stratakis M, Orfanopoulos M. Tetrahedron 2000; 56: 1595
  • 81 Clennan E L, Pace A. Tetrahedron 2005; 61: 6665
  • 82 Clennan E L. Tetrahedron 2000; 56: 9151
  • 83 Alberti M N, Orfanopoulos M, In CRC Handbook of Organic Photochemistry and Photobiology, 3rd ed.,. Griesbeck A G, Oelgemöller M, Ghetti F. CRC Boca Raton, FL 2012; p  765
    Google Scholar
  • 84 Prein M, Adam W. Angew. Chem. Int. Ed. Engl. 1996; 35: 477
  • 85 Alberti M N, Orfanopoulos M. Chem.–Eur. J. 2010; 16: 9414
  • 86 Rehbein J, Carpenter B K. Phys. Chem. Chem. Phys. 2011; 13: 20906
  • 87 Singleton D A, Hang C, Szymanski M J, Meyer M P, Leach A G, Kuwata K T, Chen J S, Greer A, Foote C S, Houk K N. J. Am. Chem. Soc. 2003; 125: 1319
  • 88 Griesbeck A G, Goldfuss B, Leven M, de Kiff A. Tetrahedron Lett. 2013; 54: 2938
  • 89 Hurst J R, Wilson S L, Schuster G B. Tetrahedron 1985; 41: 2191
  • 90 Clark Jr. B C, Jones B B, Iacobucci G A. Tetrahedron 1981; 37: 405
  • 91 Griesbeck A G, Cho M. Org. Lett. 2007; 9: 611
  • 92 Foote C S, Wexler S. J. Am. Chem. Soc. 1964; 86: 3879
  • 93 Kaanumalle L S, Shailaja J, Robbins R J, Ramamurthy V. J. Photochem. Photobiol. A 2002; 153: 55
  • 94 Kyriakopoulos J, Papastavrou A T, Panagiotou G D, Tzirakis M D, Triantafyllidis K S, Alberti M N, Bourikas K, Kordulis C, Orfanopoulos M, Lycourghiotis A. J. Mol. Catal. A: Chem. 2014; 381: 9
  • 95 Griesbeck A G, Uhlig J, Sottmann T, Belkoura L, Strey R. Chem.–Eur. J. 2012; 18: 16161
  • 96 Nardello V, Caron L, Aubry J-M, Bouttemy S, Wirth T, Saha-Möller C R, Adam W. J. Am. Chem. Soc. 2004; 126: 10692
  • 97 Griesbeck A G, El-Idreesy T T. Photochem. Photobiol. Sci. 2005; 4: 205
  • 98 Griesbeck A G, Schäfer M, Uhlig J. Adv. Synth. Catal. 2008; 350: 2104
  • 99 Griesbeck A G, El-Idreesy T T, Bartoschek A. Adv. Synth. Catal. 2004; 346: 245
  • 100 Alberti M N, Orfanopoulos M. Chem.–Eur. J. 2010; 16: 9414
  • 101 Griesbeck A G, Maptue N, Bondock S, Oelgemöller M. Photochem. Photobiol. Sci. 2003; 2: 450
  • 102 Adam W, Griesbeck A. Angew. Chem. Int. Ed. Engl. 1985; 24: 1070
  • 103 Adam W, Griesbeck A. Synthesis 1986; 1050
  • 104 Adam W, Kumar A S, Saha-Möller C R. Synthesis 1995; 1525
  • 105 Stensaas K L, McCarty B V, Touchette N M, Brock J B. Tetrahedron 2006; 62: 10683
  • 106 Vougioukalakis G C, Angelis Y, Vakros J, Panagiotou G, Kordulis C, Lycourghiotis A, Orfanopoulos M. Synlett 2004; 971
  • 107 Basavaiah D, Reddy B S, Badsara S S. Chem. Rev. 2010; 110: 5447
  • 108 Orfanopoulos M, Stratakis M, Elemes Y. J. Am. Chem. Soc. 1990; 112: 6417
  • 109 Griesbeck A G, Adam W, Bartoschek A, El-Idreesy T T. Photochem. Photobiol. Sci. 2003; 2: 877
  • 110 Bartoschek A, El-Idreesy T T, Griesbeck A G, Höinck L-O, Lex J, Miara C, Neudörfl J M. Synthesis 2005; 2433
  • 111 Griesbeck A G, El-Idreesy T T, Fiege M, Brun R. Org. Lett. 2002; 4: 4193
  • 112 Griesbeck A G, El-Idreesy T T, Höinck L-O, Lex J, Brun R. Bioorg. Med. Chem. Lett. 2005; 15: 595
  • 113 Griesbeck A G, Blunk D, El-Idreesy T T, Raabe A. Angew. Chem. Int. Ed. 2007; 46: 8883
  • 114 Griesbeck A G, Höinck L-O, Neudörfl J M. Beilstein J. Org. Chem. 2010; 6: 61
  • 115 Silveira P B, Monteiro A L. J. Mol. Catal. A: Chem. 2006; 247: 1
  • 116 Park S, Yang D, Kim K T, Jeon H B. Tetrahedron Lett. 2011; 52: 6578
  • 117 Córdova A, Sundén H, Engqvist M, Ibrahem I, Casas J. J. Am. Chem. Soc. 2004; 126: 8914
  • 118 Sundén H, Engqvist M, Casas J, Ibrahem I, Córdova A. Angew. Chem. Int. Ed. 2004; 43: 6532
  • 119 Ibrahem I, Zhao G-L, Sundén H, Córdova A. Tetrahedron Lett. 2006; 47: 4659
  • 120 Walaszek D J, Rybicka-Jasińska K, Smoleń S, Karczewski M, Gryko D. Adv. Synth. Catal. 2015; 357: 2061
  • 121 Windaus A, Brunken J. Justus Liebigs Ann. Chem. 1928; 460: 225
  • 122 Matsumoto M, Dobashi S, Kuroda K, Kondo K. Tetrahedron 1985; 41: 2154
  • 123 Dewar M J S, Thiel W. J. Am. Chem. Soc. 1977; 99: 2338
  • 124 McCarrick M A, Wu Y-D, Houk K N. J. Org. Chem. 1993; 58: 3330
  • 125 Yamaguchi K, In Singlet Oxygen. Frimer A A. CRC; Boca Raton, FL 1985. Vol.  3, p  119.
    Google Scholar
  • 126 Sevin F, McKee M L. J. Am. Chem. Soc. 2001; 123: 4591
  • 127 Bobrowski M, Liwo A, Ołdziej S, Jeziorek D, Ossowski T. J. Am. Chem. Soc. 2000; 122: 8112
  • 128 Rigaudy J, Capdevielle P, Combrisson S, Maumy M. Tetrahedron Lett. 1974; 15: 2757
  • 129 Gollnick K, Griesbeck A. Tetrahedron Lett. 1984; 25: 725
  • 130 Coşkun N, Erden I. Tetrahedron 2011; 67: 8607
  • 131 Adam W, Erden I. Angew. Chem. Int. Ed. Engl. 1978; 17: 210
  • 132 Kornblum N, De La Mare H E. J. Am. Chem. Soc. 1951; 73: 880
  • 133 Erden I, Öcal N, Song J, Gleason C, Gärtner C. Tetrahedron 2006; 62: 10676
  • 134 Erden I, Xu F P, Drummond J, Alstad R. J. Org. Chem. 1993; 58: 3611
  • 135 Georgiou T, Tofi M, Montagnon T, Vassilikogiannakis G. Org. Lett. 2006; 8: 1945
  • 136 Noutsias D, Alexopoulou I, Montagnon T, Vassilikogiannakis G. Green Chem. 2012; 14: 601
  • 137 Triantafyllakis M, Tofi M, Montagnon T, Kouridaki A, Vassilikogiannakis G. Org. Lett. 2014; 16: 3150
  • 138 Jefford C W, Rimbault C G. J. Am. Chem. Soc. 1978; 100: 6437
  • 139 Erden I, Song J, Cao W. Org. Lett. 2000; 2: 1383
  • 140 Charlton A, Donati D, Fusi S, Murphy P J, Ponticelli F. Tetrahedron Lett. 2013; 54: 1227
  • 141 Watanabe N, Sano Y, Suzuki H, Tanimura M, Ijuin H K, Matsumoto M. J. Org. Chem. 2010; 75: 5920
  • 142 Wada Y, Kaga H, Uchiito S, Kumazawa E, Tomiki M, Onozaki Y, Kurono N, Tokuda M, Ohkuma T, Orito K. J. Org. Chem. 2007; 72: 7301
  • 143 Schuster G B, Turro N J, Steinmetzer H C, Schaap A P, Faler G, Adam W, Liu J C. J. Am. Chem. Soc. 1975; 97: 7110
  • 144 De Vico L, Liu Y-J, Krogh J W, Lindh R. J. Phys. Chem. A 2007; 111: 8013
  • 145 Farahani P, Roca-Sanjuán D, Zapata F, Lindh R. J. Chem. Theory Comput. 2013; 9: 5404
  • 146 Erbas-Cakmak S, Akkaya E U. Org. Lett. 2014; 16: 2946
  • 147 Beck S, Köster H. Anal. Chem. 1990; 62: 2258
  • 148 Yuan Y, Zhang C-J, Xu S, Liu B. Chem. Sci. 2016; 7: 1862
  • 149 Toutchkine A, Aebisher D, Clennan E L. J. Am. Chem. Soc. 2001; 123: 4966
  • 150 Toutchkine A, Clennan E L. J. Org. Chem. 1999; 64: 5620
  • 151 Baciocchi E, Del Giacco T, Elisei F, Gerini M F, Guerra M, Lapi A, Liberali P. J. Am. Chem. Soc. 2003; 125: 16444
  • 152 Ramnath N, Ramesh V, Ramamurthy V. J. Org. Chem. 1983; 48: 214
  • 153 Sánchez-Arroyo A J, Pardo Z D, Moreno-Jiménez F, Herrera A, Martín N, García-Fresnadillo D. J. Org. Chem. 2015; 80: 10575
  • 154 Nakano M, Furuichi N, Mori H, Katsumura S. Tetrahedron Lett. 2001; 42: 7307