Muniz, K.: 2018 Science of Synthesis, 2017/4: Catalytic Oxidation in Organic Synthesis DOI: 10.1055/sos-SD-225-00078
Catalytic Oxidation in Organic Synthesis

3 Metal-Catalyzed Oxidation of Alkanes To Give Esters or Amines

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Book

Editor: Muniz, K.

Authors: 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.

Title: Catalytic Oxidation in Organic Synthesis

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

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

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

Type: Multivolume Edition

 

Abstract

The modification of relatively unreactive alkanes of general formula CnH2n+2, as well as of cycloalkanes CnH2n, by oxidation of C—H bonds in a catalytic manner is reviewed, focusing on their direct conversions into esters or amines upon incorporation of carbene or nitrene fragments, respectively.

 
  • 1 Activation and Functionalization of C–H Bonds. Goldberg K I, Goldman A S. Eds.; ACS Symposium Series 885; American Chemical Society; Washington, DC 2004
  • 2 Handbook of C–H Transformations. Dyker G. Wiley-VCH; Weinheim, Germany 2005. Vol. 1.
  • 3 Shilov A E, Shulʼpin G B. Activation and Catalytic Reactions of Saturated Hydrocarbons in the Presence of Metal Complexes,. Kluwer; Dordrecht, The Netherlands 2000. Vol. 21.
  • 4 Arpe H-J. Industral Organic Chemistry, 5th ed.,. Wiley-VCH; Weinheim, Germany 2010
  • 5 Alkane C–H Activation by Single-Site Metal Catalysis. Pérez P J. Springer; Dordrecht, The Netherlands 2012. Vol.  38.
  • 6 Gunnoe T B, In Physical Inorganic Chemistry: Reactions, Processes, and Applications. Bakac A. Wiley Hoboken, NJ 2010; p  495
  • 7 Luo Y-R. Comprehensive Handbook of Chemical Bond Energies. CRC; Boca Raton, FL 2007
  • 8 Pauling L. J. Am. Chem. Soc. 1932; 54: 3570
  • 9 Periana R A, Taube D J, Gamble S, Taube H, Satoh T, Fujii H. Science (Washington, D. C.) 1998; 280: 560
  • 10 Mkhalid I A I, Barnard J H, Marder T B, Murphy J M, Hartwig J F. Chem. Rev. 2010; 110: 890
  • 11 Jensen C M. Chem. Commun. (Cambridge) 1999; 2443
  • 12 Goldman A S, Roy A H, Huang Z, Ahuja R, Schinski W, Brookhart M. Science (Washington, D. C.) 2006; 312: 257
  • 13 Caballero A, Díaz-Requejo M M, Fructos M R, Olmos A, Urbano J, Pérez P J. Dalton Trans. 2015; 44: 20 295
  • 14 Davies H M L, Manning J R. Nature (London) 2008; 451: 417
  • 15 Díaz-Requejo M M, Pérez P J. Chem. Rev. 2008; 108: 3379
  • 16 Díaz-Requejo M M, Belderrain T R, Nicasio M C, Pérez P J. Dalton Trans. 2006; 5559
  • 17 Zalatan D N, Du Bois J. Top. Curr. Chem. 2010; 292: 347
  • 18 Halfen J A. Curr. Org. Chem. 2005; 9: 657
  • 19 Müller P, Fruit C. Chem. Rev. 2003; 103: 2905
  • 20 Uchida T, Katsuki T. Chem. Rec. 2014; 14: 117
  • 21 Cheng Q-Q, Doyle M P. Adv. Organomet. Chem. 2016; 66: 1
  • 22 Doyle M P, McKervey M A, Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds. Wiley; New York 1998
  • 23 Doyle M P, In Comprehensive Organometallic Chemistry II. Abel E W, Stone F G A, Wilkinson G. Pergamon; Oxford 1995. Vol.  12, p 421.
  • 24 Silberrad O, Roy C S. J. Chem. Soc. 1906; 89: 179
  • 25 Yates P. J. Am. Chem. Soc. 1952; 74: 5376
  • 26 Nozaki H, Moriuti S, Takaya H, Noyori R. Tetrahedron Lett. 1966; 5239
  • 27 Moser W R. J. Am. Chem. Soc. 1969; 91: 1135
  • 28 Moser W R. J. Am. Chem. Soc. 1969; 91: 1141
  • 29 Maxwell J L, Brown K C, Bartley D W, Kodadek T. Science (Washington, D. C.) 1992; 256: 1544
  • 30 Kornecki K P, Briones J F, Boyarskikh V, Fullilove F, Autschbach J, Schrote K E, Lancaster K M, Davies H M L, Berry J F. Science (Washington, D. C.) 2013; 342: 351
  • 31 Collman J P, Rose E, Venburg G D. J. Chem. Soc., Chem. Commun. 1993; 934
  • 32 Smith D A, Reynolds D N, Woo L K. J. Am. Chem. Soc. 1993; 115: 2511
  • 33 Galardon E, Le Maux P, Toupet L, Simonneaux G. Organometallics 1998; 17: 565
  • 34 Deng Q-H, Chen J, Huang J-S, Chui S S-Y, Zhu N, Li G-Y, Che C-M. Chem.–Eur. J. 2009; 15: 10 707
  • 35 Park S-B, Sakata N, Nishiyama H. Chem.–Eur. J. 1996; 2: 303
  • 36 Nishiyama H, Aoki K, Itoh H, Iwamura T, Sakata N, Kurihara O, Motoyama Y. Chem. Lett. 1996; 25: 1071
  • 37 Lee H M, Bianchini C, Jia G, Barbaro P. Organometallics 1999; 18: 1961
  • 38 Ranocchiari M, Mezzetti A. Organometallics 2009; 28: 3611
  • 39 Lu H, Dzik W I, Xu X, Wojtas L, de Bruin B, Zhang X P. J. Am. Chem. Soc. 2011; 133: 8518
  • 40 Mindiola D J, Hillhouse G L. J. Am. Chem. Soc. 2002; 124: 9976
  • 41 Waterman R, Hillhouse G L. J. Am. Chem. Soc. 2003; 125: 13 350
  • 42 Iluc V M, Hillhouse G L. J. Am. Chem. Soc. 2014; 136: 6479
  • 43 Straub B F, Hofmann P. Angew. Chem. Int. Ed. 2001; 40: 1288
  • 44 Barluenga J, López L A, Löber O, Tomás M, García-Granda S, Álvarez-Rúa C, Borge J. Angew. Chem. Int. Ed. 2001; 40: 3392
  • 45 Dai X L, Warren T H. J. Am. Chem. Soc. 2004; 126: 10 085
  • 46 Mankad N P, Peters J C. Chem. Commun. (Cambridge) 2008; 1061
  • 47 Pereira A, Champouret Y, Martín C, Álvarez E, Etienne M, Belderrain T R, Pérez P J. Chem.–Eur. J. 2015; 21: 9769
  • 48 Hussong M W, Rominger F, Krämer P, Straub B F. Angew. Chem. Int. Ed. 2014; 53: 9372
  • 49 Joost M, Estévez L, Mallet-Ladeira S, Miqueu K, Amgoune A, Bourissou D. Angew. Chem. Int. Ed. 2014; 53: 14 512
  • 50 Hofmann P, Shishkov I V, Rominger F. Inorg. Chem. 2008; 47: 11 755
  • 51 Shishkov I V, Rominger F, Hofmann P. Organometallics 2009; 28: 1049
  • 52 Hussong M W, Hoffmeister W T, Rominger F, Straub B F. Angew. Chem. Int. Ed. 2015; 54: 10 331
  • 53 Braga A A C, Maseras F, Urbano J, Caballero A, Díaz-Requejo M M, Pérez P J. Organometallics 2006; 25: 5292
  • 54 Braga A A C, Caballero A, Urbano J, Díaz-Requejo M M, Pérez P J, Maseras F. ChemCatChem 2011; 3: 1646
  • 55 Besora M, Braga A A C, Sameera W M C, Urbano J, Fructos M R, Pérez P J, Maseras F. J. Organomet. Chem. 2015; 784: 2
  • 56 Rivilla I, Sameera W M C, Álvarez E, Díaz-Requejo M M, Maseras F, Pérez P J. Dalton Trans. 2013; 42: 4132
  • 57 Scott L T, DeCicco G J. J. Am. Chem. Soc. 1974; 96: 322
  • 58 Wulfman D S, McDaniel Jr. R S, Peace B W. Tetrahedron 1976; 32: 1241
  • 59 Demonceau A, Noels A F, Hubert A J, Teyssié P. J. Chem. Soc., Chem. Commun. 1981; 688
  • 60 Demonceau A, Noels A F, Hubert A J, Teyssié P. Bull. Soc. Chim. Belg. 1984; 93: 945
  • 61 Davies H M L, Hansen T, Churchill M R J. J. Am. Chem. Soc. 2000; 122: 3063
  • 62 Endres A, Maas G. J. Organomet. Chem. 2002; 643: 174
  • 63 Demonceau A, Noels A F, Teyssié P, Hubert A J. J. Mol. Catal. 1988; 49: L13
  • 64 Demonceau A, Noels A F, Hubert A J. J. Mol. Catal. 1989; 57: 149
  • 65 Demonceau A, Noels A F, Costa J-L, Hubert A J. J. Mol. Catal. 1990; 58: 21
  • 66 Davies H M L, Hansen T. J. Am. Chem. Soc. 1997; 119: 9075
  • 67 Davies H M L, Antoulinakis E G. J. Organomet. Chem. 2001; 617–618: 47
  • 68 Callot H J, Metz F. Tetrahedron Lett. 1982; 23: 4321
  • 69 Thu H-Y, Tong G S-M, Huang J-S, Chan S L-F, Deng Q-H, Che C-M. Angew. Chem. Int. Ed. 2008; 47: 9747
  • 70 Callot H J, Metz F. Nouv. J. Chim. 1985; 9: 167
  • 71 Díaz-Requejo M M, Belderrain T R, Nicasio M C, Trofimenko S, Pérez P J. J. Am. Chem. Soc. 2002; 124: 896
  • 72 Fructos M R, de Frémont P, Nolan S P, Díaz-Requejo M M, Pérez P J. Organometallics 2006; 25: 2237
  • 73 Caballero A, Díaz-Requejo M M, Belderrain T R, Nicasio M C, Trofimenko S, Pérez P J. J. Am. Chem. Soc. 2003; 125: 1446
  • 74 Caballero A, Díaz-Requejo M M, Belderrain T R, Nicasio M C, Trofimenko S, Pérez P J. Organometallics 2003; 22: 4145
  • 75 Rangan K, Fianchini M, Singh S, Dias H V R. Inorg. Chim. Acta 2009; 362: 4347
  • 76 Pérez J, Morales D, García-Escudero L A, Martínez-García H, Miguel D, Bernad P. Dalton Trans. 2009; 375
  • 77 Despagnet-Ayoub E, Jacob K, Vendier L, Etienne M, Álvarez E, Caballero A, Díaz-Requejo M M, Pérez P J. Organometallics 2008; 27: 4779
  • 78 Gava R, Olmos A, Noverges B, Varea T, Funes-Ardoiz I, Belderrain T R, Caballero A, Maseras F, Asensio G, Pérez P J. ChemCatChem 2015; 7: 3254
  • 79 Dias H V R, Browning R G, Richey S A, Lovely C J. Organometallics 2004; 23: 1200
  • 80 Dias H V R, Browning R G, Richey S A, Lovely C J. Organometallics 2005; 24: 5784
  • 81 Urbano J, Belderrain T R, Nicasio M C, Trofimenko S, Díaz-Requejo M M, Pérez P J. Organometallics 2005; 24: 1528
  • 82 Lovely C J, Flores J A, Meng X, Dias H V R. Synlett 2009; 129
  • 83 Rodríguez P, Álvarez E, Nicasio M C, Pérez P J. Organometallics 2007; 26: 6661
  • 84 Fuentes M Á, Muñoz B K, Jacob K, Vendier L, Caballero A, Etienne M, Pérez P J. Chem.–Eur. J. 2013; 19: 1327
  • 85 Fuentes M Á, Rodríguez-Castillo M, Monge M, Olmos M E, López de Luzuriaga J M, Caballero A, Pérez P J. Inorg. Chim. Acta 2011; 369: 146
  • 86 Flores J A, Komine N, Pal K, Pinter B, Pink M, Chen C-H, Caulton K G, Mindiola D J. ACS Catal. 2012; 2: 2066
  • 87 Mbuvi H M, Woo L K. Organometallics 2008; 27: 637
  • 88 Choi M K-W, Yu W-Y, So M-H, Zhou C-Y, Deng Q-H, Che C-M. Chem.–Asian J. 2008; 3: 1256
  • 89 Kulkarni N V, Dash C, Jayaratna N B, Ridlen S G, Khani S K, Das A, Kou X, Yousufuddin M, Cundari T R, Dias H V R. Inorg. Chem. 2015; 54: 11 043
  • 90 Caballero A, Despagnet-Ayoub E, Díaz-Requejo M M, Díaz-Rodríguez A, González-Núñez M E, Mello R, Muñoz B K, Ojo W-S, Asensio G, Etienne M, Pérez P J. Science (Washington, D. C.) 2011; 332: 835
  • 91 Fuentes M Á, Olmos A, Muñoz B K, Jacob K, González-Núñez M E, Mello R, Asensio G, Caballero A, Etienne M, Pérez P J. Chem.–Eur. J. 2014; 20, 11: 013
  • 92 Gava R, Olmos A, Noverges B, Varea T, Álvarez E, Belderrain T R, Caballero A, Asensio G, Pérez P J. ACS Catal. 2015; 5: 3726
  • 93 Liao K, Negretti S, Musaev D G, Bacsa J, Davies H M L. Nature (London) 2016; 533: 230
  • 94 Modern Amination Methods. Ricci A. Wiley-VCH; Weinheim, Germany 2000
  • 95 Amino Group Chemistry: From Synthesis to the Life Sciences. Ricci A. Wiley; Weinheim, Germany 2008
  • 96 Royer J, In Asymmetric Synthesis of Nitrogen Heterocycles. Royer J. Wiley-VCH Weinheim, Germany 2009; pp  367
  • 97 Nugent T C, In Chiral Amine Synthesis: Methods, Developments and Applications. Nugent T C. Wiley-VCH Weinheim, Germany 2010; p  225
  • 98 Hili R, Yudin A K. Nat. Chem. Biol. 2006; 2: 284
  • 99 Catalyzed Carbon–Heteroatom Bond Formation. Yudin A K. Wiley-VCH; Weinheim, Germany 2011
  • 100 Hartwig J F. Nature (London) 2008; 455: 314
  • 101 Lu H, Zhang X P. Chem. Soc. Rev. 2011; 40: 1899
  • 102 Che C-M, Lo V K-Y, Zhou C-Y, Huang J-S. Chem. Soc. Rev. 2011; 40: 1950
  • 103 Breslow D S, Sloan M F. Tetrahedron Lett. 1968; 5349
  • 104 Breslow R, Gellman S H. J. Chem. Soc., Chem. Commun. 1982; 1400
  • 105 Yamada Y, Yamamoto T, Okawara M. Chem. Lett. 1975; 361
  • 106 Södergren M J, Alonso D A, Bedekar A V, Andersson P G. Tetrahedron Lett. 1997; 38: 6897
  • 107 Gómez-Emeterio B P, Urbano J, Díaz-Requejo M M, Pérez P J. Organometallics 2008; 27: 4126
  • 108 Li Z, Capretto D A, Rahaman R O, He C. Angew. Chem. Int. Ed. 2007; 46: 5184
  • 109 Díaz-Requejo M M, Belderrain T R, Nicasio M C, Trofimenko S, Pérez P J. J. Am. Chem. Soc. 2003; 125: 12 078
  • 110 Fructos M R, Trofimenko S, Díaz-Requejo M M, Pérez P J. J. Am. Chem. Soc. 2006; 128: 11784
  • 111 Bagchi V, Paraskevopoulou P, Das P, Chi L, Wang Q, Choudhury A, Mathieson J S, Cronin L, Pardue D B, Cundari T R, Mitrikas G, Sanakis Y, Stavropoulos P. J. Am. Chem. Soc. 2014; 136: 11 362
  • 112 Liu Y, Guan X, Wong E L-M, Liu P, Huang J-S, Che C-M. J. Am. Chem. Soc. 2013; 135: 7194
  • 113 Nägeli I, Baud C, Bernardelli G, Jacquier Y, Moraon M, Müller P. Helv. Chim. Acta 1997; 80: 1087
  • 114 Yu X-Q, Huang J-S, Zhou X-G, Che C-M. Org. Lett. 2000; 2: 2233
  • 115 Au S-M, Huang J-S, Che C-M, Yu W-Y. J. Org. Chem. 2000; 65: 7858
  • 116 Kalita B, Lamar A A, Nicholas K M. Chem. Commun. (Cambridge) 2008; 4291
  • 117 Barton D H R, Hay-Motherwell R S, Motherwell W B. J. Chem. Soc., Perkin Trans. 1 1983; 445
  • 118 Barman D N, Liu P, Houk K N, Nicholas K M. Organometallics 2010; 29: 3404
  • 119 Albone D P, Challenger S, Derrick A M, Fillery S M, Irwin J L, Parsons C M, Takada H, Taylor P C, Wilson D J. Org. Biomol. Chem. 2005; 3: 107
  • 120 Wehn P M, Du Bois J. J. Am. Chem. Soc. 2002; 124: 12 950
  • 121 Hinman A, Du Bois J. J. Am. Chem. Soc. 2003; 125: 11 510
  • 122 Parker K A, Chang W. Org. Lett. 2003; 5: 3891
  • 123 Tanino T, Ichikawa S, Matsuda A. Org. Lett. 2011; 13: 4028
  • 124 Huters A D, Quasdorf K W, Styduhar E D, Garg N K. J. Am. Chem. Soc. 2011; 133: 15 797
  • 125 Takahashi K, Yamaguchi D, Ishihara J, Hatakeyama S. Org. Lett. 2012; 14: 1644
  • 126 Liang C, Robert-Peillard F, Fruit C, Müller P, Dodd R H, Dauban P. Angew. Chem. Int. Ed. 2006; 45: 4641
  • 127 Liang C, Collet F, Robert-Peillard F, Müller P, Dodd R H, Dauban P. J. Am. Chem. Soc. 2008; 130: 343
  • 128 Lescot C, Darses B, Collet F, Retailleau P, Dauban P. J. Org. Chem. 2012; 77: 7232
  • 129 Espino C G, Fiori K W, Kim M, Du Bois J. J. Am. Chem. Soc. 2004; 126: 15 378
  • 130 Roizen J L, Zalatan D N, Du Bois J. Angew. Chem. Int. Ed. 2013; 52: 11 343
  • 131 Kwart H, Khan A A. J. Am. Chem. Soc. 1967; 89: 1951
  • 132 Intrieri D, Zardi P, Caselli A, Gallo E. Chem. Commun. (Cambridge) 2014; 50: 11 440
  • 133 Badiei Y M, Dinescu A, Dai X, Palomino R M, Heinemann F W, Cundari T R, Warren T H. Angew. Chem. Int. Ed. 2008; 47: 9961
  • 134 Liu Y, Che C-M. Chem.–Eur. J. 2010; 16: 10 494
  • 135 Xiao W, Wei J, Zhou C-Y, Che C-M. Chem. Commun. (Cambridge) 2013; 49: 4619
  • 136 Chan K-H, Guan X, Lo V K-Y, Che C-M. Angew. Chem. Int. Ed. 2014; 53: 2982
  • 137 Suárez J R, Chiara J L. Chem. Commun. (Cambridge) 2013; 49: 9194
  • 138 Beltrán A, Lescot C, Díaz-Requejo M M, Pérez P J, Dauban P. Tetrahedron 2013; 69: 4488
  • 139 Chikkade P K, Kuninobu Y, Kanai M. Chem. Sci. 2015; 6: 3195
  • 140 Wei Z, Li J, Wang N, Zhang Q, Shi D, Sun K. Tetrahedron 2014; 70: 1395
  • 141 Pelletier G, Powell D A. Org. Lett. 2006; 8: 6031
  • 142 Wiese S, Badiei Y M, Gephart R T, Mossin S, Varonka M S, Melzer M M, Meyer K, Cundari T R, Warren T H. Angew. Chem. Int. Ed. 2010; 49: 8850
  • 143 Gephart R T, Huang D L, Aguila M J B, Schmidt G, Shahu A, Warren T H. Angew. Chem. Int. Ed. 2012; 51: 6488
  • 144 Mann G, Hartwig J F. J. Am. Chem. Soc. 1996; 118: 13 109
  • 145 Wolfe J P, Wagaw S, Marcoux J-F, Buchwald S L. Acc. Chem. Res. 1998; 31: 805
  • 146 Hartwig J F. Angew. Chem. Int. Ed. 1998; 37: 2046
  • 147 Jang E S, McMullin C L, Käß M, Meyer K, Cundari T R, Warren T H. J. Am. Chem. Soc. 2014; 136: 10 930
  • 148 Xia R, Niu H-Y, Qu G-R, Guo H-M. Org. Lett. 2012; 14: 5546
  • 149 Tran B L, Li B, Driess M, Hartwig J F. J. Am. Chem. Soc. 2014; 136: 2555
  • 150 Zeng H-T, Huang J-M. Org. Lett. 2015; 17: 4276