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High-Valent Iron in Biomimetic Alkane Oxidation Catalysis

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Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 50))

Abstract

The combination of iron salts or complexes with strong oxidants such as hydrogen peroxide results in the formation of high-valent iron oxo species, the nature of which has been under discussion in the chemical literature for more than a century. Recent advances in the design and development of molecular iron-based oxidation catalysts and their mechanistic understanding are summarised in this chapter, in particular iron complexes featuring tetradentate and pentadentate ligands. Inspired by enzymatic systems based on heme and nonheme ligand environments, the development of biomimetic iron-based catalysts for the selective oxidation of alkanes and alkenes can potentially be applied in a range of areas, from late stage functionalisation of natural product synthesis to large-scale oxidation of hydrocarbons.

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Abbreviations

BLM:

Bleomycin

DFT:

Density functional theory

DNA:

Deoxyribonucleic acid

EPR:

Electron paramagnetic resonance

HAT:

Hydrogen atom transfer

His:

Histidine

KIE:

Kinetic isotope effect

MMO:

Methane monooxygenase

NMR:

Nuclear magnetic resonance

PCET:

Proton-coupled electron transfer

RC:

Retention of configuration

References

  1. Merkx M, Kopp DA, Sazinsky MH, Blazyk JL, Muller J, Lippard S (2001) Angew Chem Int Ed 40:2782

    CAS  Google Scholar 

  2. Balasubramanian R, Rosenzweig AC (2007) Acc Chem Res 40:573

    CAS  Google Scholar 

  3. Costas M, Mehn MP, Jensen MP, Que L Jr (2004) Chem Rev 104:939

    CAS  Google Scholar 

  4. Sono M, Roach MP, Coulter ED, Dawson JH (1996) Chem Rev 96:2841

    CAS  Google Scholar 

  5. Law NA, Caudle MT, Pecoraro VL (1999) Adv Inorg Chem 46:305

    Google Scholar 

  6. Krebs C, Fujimori GD, Walsh CT, Bollinger JM Jr (2007) Acc Chem Res 40:484

    CAS  Google Scholar 

  7. Abu-Omar MM, Loaiza A, Hontzeas N (2005) Chem Rev 105:2227

    CAS  Google Scholar 

  8. Neidig ML, Solomon EI (2005) Chem Commun 41:5843

    Google Scholar 

  9. Nam W (2007) Acc Chem Res 40:522

    CAS  Google Scholar 

  10. Que L Jr (2007) Acc Chem Res 40:493

    CAS  Google Scholar 

  11. MacBeth CE, Golombek AP, Young VG, Kuczera K, Hendrich MP, Borovik AS (2000) Science 289:938

    CAS  Google Scholar 

  12. Kovacs JA (2003) Science 299:1024

    CAS  Google Scholar 

  13. Meunier B, de Visser SP, Shaik S (2004) Chem Rev 104:3947

    CAS  Google Scholar 

  14. Harris DL, Loew GH (1998) J Am Chem Soc 120:8941

    CAS  Google Scholar 

  15. Karlsson A, Parales JV, Parales RE, Gibson DT, Eklund H, Ramaswamy S (2003) Science 299:1039

    CAS  Google Scholar 

  16. Chen K, Costas M, Que Jr L (2002) J Chem Soc Dalton Trans: 672

    Google Scholar 

  17. Solomon EI (2001) Inorg Chem 40:3656

    CAS  Google Scholar 

  18. Groves JT (1985) J Chem Educ 62:928

    CAS  Google Scholar 

  19. Que L Jr, Ho YNR (1996) Chem Rev 96:2607

    CAS  Google Scholar 

  20. Ho RYN, Que L Jr, Roelfes G, Feringa BL, Hermant R, Hage R (1999) Chem Commun 21:2161

    Google Scholar 

  21. Neese F, Solomon EI (1998) J Am Chem Soc 120:12829

    CAS  Google Scholar 

  22. Decker A, Solomon EI (2005) Curr Opin Chem Biol 9:152

    CAS  Google Scholar 

  23. Hegg EL, Que L Jr (1997) Eur J Biochem 250:625

    CAS  Google Scholar 

  24. Lehnert N, DeBeer George S, Solomon EI (2001) Curr Opin Chem Biol 5:176

    CAS  Google Scholar 

  25. Solomon EI, Brunold TC, Davis MI, Kemsley JN, Lee SK, Lehnert N, Neese F, Skulan AJ, Yang YS, Zhou J (2000) Chem Rev 100:235

    CAS  Google Scholar 

  26. Solomon EI, Randall DW, Glaser T (2000) Coord Chem Rev 200–202:595

    Google Scholar 

  27. Bugg TDH, Ramaswamy S (2008) Curr Opin Chem Biol 12:134

    CAS  Google Scholar 

  28. Ullrich R, Hofrichter M (2007) Cell Mol Life Sci 64:271

    CAS  Google Scholar 

  29. Que L Jr (2000) Nat Struct Biol 7:182

    CAS  Google Scholar 

  30. Moelands MAH, Nijsse S, Folkertsma E, de Bruin B, Lutz M, Spek AL, Klein Gebbink RJM (2013) Inorg Chem 52:7394

    CAS  Google Scholar 

  31. Solomon EI, Decker A, Lehnert N (2003) Proc Natl Acad Sci U S A 100:3589

    CAS  Google Scholar 

  32. Hufton SE, Jennings IG, Cotton RGH (1995) Biochem J 311:353

    CAS  Google Scholar 

  33. Ohlendorf DH, Orville AM, Lipscomb JD (1994) J Mol Biol 244:586

    CAS  Google Scholar 

  34. Ohlendorf DH, Lipscomb JD, Weber PC (1988) Nature 336:403

    CAS  Google Scholar 

  35. Eltis LD, Bolin JT (1996) J Bacteriol 178:5930

    CAS  Google Scholar 

  36. Miller AF (2001) Handbook of metalloproteins. Wiley, Chichester

    Google Scholar 

  37. Roach PL, Clifton IJ, Fulop V, Harlos K, Barton GJ, Hajdu J, Andersson I, Schofield CJ, Baldwin JE (1995) Nature 375:700

    CAS  Google Scholar 

  38. Schofield CJ, Zhang Z (1999) Curr Opin Struct Biol 9:722

    CAS  Google Scholar 

  39. Schenk WA (2000) Angew Chem Int Ed 39:3409

    CAS  Google Scholar 

  40. Roach PL, Clifton IJ, Hensgens CMH, Shibata N, Long AJ, Strange RW, Hasnain SS, Schofield CJ, Baldwin JE, Hajdu J (1996) Eur J Biochem 242:736

    CAS  Google Scholar 

  41. Orville AM, Chen VJ, Kriauciunas A, Harpel MR, Fox BG, Munck E, Lipscomb JD (1992) Biochemistry 31:4602

    CAS  Google Scholar 

  42. Baldwin JE, Bradley M (1990) Chem Rev 90:1079

    CAS  Google Scholar 

  43. Nanda S, Yadav JS (2003) J Mol Catal B: Enzym 26:3

    CAS  Google Scholar 

  44. Minor W, Steczko J, Stec B, Otwinowski Z, Bolin JT, Walter R, Axelrod B (1996) Biochemistry 35:10687

    CAS  Google Scholar 

  45. Kauppi B, Lee K, Carredano E, Parales RE, Gibson DT, Eklund H, Ramaswamy S (1998) Structure 6:571

    CAS  Google Scholar 

  46. Stubbe J, Kozarich JW, Wu W, Vanderwall DE (1996) Acc Chem Res 29:322

    CAS  Google Scholar 

  47. Rosenzweig AC, Frederick CA, Lippard SJ, Nordlund P (1993) Nature 366:537

    CAS  Google Scholar 

  48. Wallar BJ, Lipscomb JD (1996) Chem Rev 96:2625

    CAS  Google Scholar 

  49. Sam JW, Tang XJ, Peisach J (1994) J Am Chem Soc 116:5250

    CAS  Google Scholar 

  50. Stubbe J, Kozarich JW (1987) Chem Rev 87:1107

    CAS  Google Scholar 

  51. Neese F, Zaleski JM, Zaleski KL, Solomon EI (2000) J Am Chem Soc 122:11703

    CAS  Google Scholar 

  52. Absalon MJ, Wu W, Kozarich JW, Stubbe J (1995) J Am Chem Soc 34:2076

    CAS  Google Scholar 

  53. Westre TE, Loeb KE, Zaleski JM, Hedman B, Hodgson KO, Solomon EI (1995) J Am Chem Soc 117:1309

    CAS  Google Scholar 

  54. Guajardo RJ, Hudson SE, Brown SJ, Mascharak PK (1993) J Am Chem Soc 115:7971

    CAS  Google Scholar 

  55. Loeb KE, Zaleski JM, Westre TE, Guajardo RJ, Mascharak PK, Hedman B, Hodgson KO, Solomon EI (1995) J Am Chem Soc 117:4545

    CAS  Google Scholar 

  56. Guajardo RJ, Chavez F, Farinas ET, Mascharak PK (1995) J Am Chem Soc 117:3883

    CAS  Google Scholar 

  57. Baik MH, Newcomb M, Friesner RA, Lippard SJ (2003) Chem Rev 103:2385

    CAS  Google Scholar 

  58. Tshuva EY, Lippard SJ (2004) Chem Rev 104:987

    CAS  Google Scholar 

  59. Costas M, Chen K, Que L Jr (2000) Coord Chem Rev 200–202:517

    Google Scholar 

  60. Shu L, Nesheim JC, Kauffmann KE, Munck E, Lipscomb JD, Que L Jr (1997) Science 275:515

    CAS  Google Scholar 

  61. Partenheimer W (1995) Catal Today 23:69

    CAS  Google Scholar 

  62. Fenton HJH (1894) J Chem Soc Trans 65:889

    Google Scholar 

  63. Gozzo F (2001) J Mol Catal A Chem 171:1

    CAS  Google Scholar 

  64. Dunford HB (2002) Coord Chem Rev 233–234:311

    Google Scholar 

  65. Goldstein AS, Drago RS (1991) Inorg Chem 30:4506

    CAS  Google Scholar 

  66. Haber F, Weiss J (1934) Proc R Soc London Ser A 147:332

    CAS  Google Scholar 

  67. Russell GA (1957) J Am Chem Soc 79:3871

    CAS  Google Scholar 

  68. Tanase S, Bouwman E (2006) Adv Inorg Chem 58:29

    CAS  Google Scholar 

  69. Talsi EP, Chinakov VD, Babenko VP, Sidelnikov VN, Zamaraev KI (1993) J Mol Catal 81:215

    CAS  Google Scholar 

  70. Meunier B (1992) Chem Rev 92:1411

    CAS  Google Scholar 

  71. Nam W, Oh S-Y, Sun YJ, Kim J, Kim W-K, Woo SK, Shin W (2003) J Org Chem 68:7903

    CAS  Google Scholar 

  72. Srinivas KA, Kumar A, Chauhan SMS (2002) Chem Commun 38:2456

    Google Scholar 

  73. Stephenson NA, Bell AT (2005) J Am Chem Soc 127:8635

    CAS  Google Scholar 

  74. Sorokin AB, Kudrik EV, Bouchu D (2008) Chem Commun 44:2562

    Google Scholar 

  75. Cunningham ID, Danks TN, Hay JN, Hamerton I, Gunathilagan S (2001) Tetrahedron 57:6847

    CAS  Google Scholar 

  76. Cunningham ID, Danks TN, Hay JN, Hamerton I, Gunathilagan S, Janczak C (2002) J Mol Catal 185:25

    CAS  Google Scholar 

  77. Cunningham ID, Danks TN, O’Connell KTA, Scott PW (1999) J Chem Soc Perkin Trans 2: 2133

    Google Scholar 

  78. Serra AC, Marçalo EC, Rocha Gonsalves AMdA (2004) J Mol Catal 215:17

    CAS  Google Scholar 

  79. Nappa MJ, Tolman CA (1985) Inorg Chem 24:4711

    CAS  Google Scholar 

  80. Goh YM, Nam W (1999) Inorg Chem 38:914

    CAS  Google Scholar 

  81. Nam W, Jin SW, Lim MH, Ryu JY, Kim C (2002) Inorg Chem 41:3647

    CAS  Google Scholar 

  82. Hill CL, Prosser-McCartha CM (1995) Coord Chem Rev 143:407

    CAS  Google Scholar 

  83. Barton DHR, Doller D (1992) Acc Chem Res 25:504

    CAS  Google Scholar 

  84. Barton DHR (1996) Chem Soc Rev 25:237

    CAS  Google Scholar 

  85. Sawyer DT, Sobkowiak A, Matsushita T (1996) Acc Chem Res 29:409

    CAS  Google Scholar 

  86. Sawyer DT (1997) Coord Chem Rev 165:297

    CAS  Google Scholar 

  87. Vincent JB, Huffman JC, Christou G, Li Q, Nanny MA, Hendrickson DN, Fong RH, Fish RH (1988) J Am Chem Soc 110:6898

    CAS  Google Scholar 

  88. Rabion A, Buchanan RM, Seris JL, Fish RH (1997) J Mol Catal A Chem 116:43

    CAS  Google Scholar 

  89. Neimann K, Neumann R, Rabion A, Buchanan RM, Fish RH (1999) Inorg Chem 38:3575

    CAS  Google Scholar 

  90. Kim C, Chen K, Kim J, Que L Jr (1997) J Am Chem Soc 119:5964

    CAS  Google Scholar 

  91. Chen K, Que L Jr (2001) J Am Chem Soc 123:6327

    CAS  Google Scholar 

  92. Leising RA, Norman RE, Que L Jr (1990) Inorg Chem 29:2553

    CAS  Google Scholar 

  93. Ménage S, Vincent JM, Lambeaux C, Chottard G, Grand A, Fontecave M (1993) Inorg Chem 32:4766

    Google Scholar 

  94. Nguyen C, Guajardo RJ, Mascharak PK (1996) Inorg Chem 35:6273

    CAS  Google Scholar 

  95. Lane BS, Burgess K (2003) Chem Rev 103:2457

    CAS  Google Scholar 

  96. Talsi EP, Bryliakov KP (2012) Coord Chem Rev 256:1418

    CAS  Google Scholar 

  97. Ménage S, Vincent JM, Lambeaux C, Fontecave M (1996) J Mol Catal A Chem 113:61

    Google Scholar 

  98. Kulikova VS, Gritsenko ON, Shteinman AA (1996) Mendeleev Commun 6:119

    Google Scholar 

  99. Duboc-Toia C, Ménage S, Lambeaux C, Fontecave M (1997) Tetrahedron Lett 38:3727

    CAS  Google Scholar 

  100. Chen K, Que L Jr (1999) Chem Commun 35:1375

    Google Scholar 

  101. Costas M, Que L Jr (2002) Angew Chem Int Ed 41:2179

    CAS  Google Scholar 

  102. Mekmouche Y, Ménage S, Toia-Duboc C, Fontecave M, Galey J-B, Lebrun C, Pécaut J (2001) Angew Chem Int Ed 40:949

    CAS  Google Scholar 

  103. Ho RYN, Roelfes G, Feringa BL, Que L Jr (1999) J Am Chem Soc 121:264

    CAS  Google Scholar 

  104. Bassan A, Blomberg MRA, Siegbahn PEM, Que L Jr (2002) J Am Chem Soc 124:11056

    CAS  Google Scholar 

  105. Duboc-Toia C, Menge S, Ho RYN, Que L Jr, Fontecave M (1999) Inorg Chem 38:1261

    CAS  Google Scholar 

  106. Hummel H, Mekmouche Y, Duboc-Toia C, Ho RYN, Que L Jr, Thomas F, Trautwein A, Lebrun C, Fontecave M, Ménage S (2002) Angew Chem Int Ed 41:617

    CAS  Google Scholar 

  107. Mekmouche Y, Hummel H, Ho RYN, Que L Jr, Schunemann V, Thomas F, Trautwein AX, Lebrun C, Gorgy K, Lepretre J-C, Collomb M-N, Deronzier A, Fontecave M, Menage S (2002) Chem Eur J 8:1196

    CAS  Google Scholar 

  108. Jensen MP, Costas M, Ho RYN, Kaizer J, Payeras AM, Muenck E, Que L Jr, Rohde J-U, Stubna A (2005) J Am Chem Soc 127:10512

    CAS  Google Scholar 

  109. Tiago de Oliveira F, Chanda A, Banerjee D, Shan X, Mondal S, Que L Jr, Bominaar EL, Muenck E, Collins TJ (2007) Science 315:835

    CAS  Google Scholar 

  110. Britovsek GJP, England J, White AJP (2005) Inorg Chem 44:8125

    CAS  Google Scholar 

  111. Ito S, Suzuki M, Kobayashi T, Itoh H, Harada A, Ohba S, Nishida Y (1996) J Chem Soc Dalton Trans: 2579

    Google Scholar 

  112. Klopstra M, Roelfes G, Hage R, Kellogg RM, Feringa BL (2004) Eur J Inorg Chem: 846

    Google Scholar 

  113. Gutkina EA, Rubtsova TB, Shteinman AA (2003) Kinet Catal 44:106

    CAS  Google Scholar 

  114. Gómez L, Garcia-Bosch I, Company A, Benet-Buchholz J, Polo A, Sala X, Ribas X, Costas M (2009) Angew Chem Int Ed 48:5720

    Google Scholar 

  115. England J, Britovsek GJP, Rabadia N, White AJP (2007) Inorg Chem 46:3752

    CAS  Google Scholar 

  116. Chen K, Costas M, Kim J, Tipton AK, Que L Jr (2002) J Am Chem Soc 124:3026

    CAS  Google Scholar 

  117. White MC, Doyle AG, Jacobsen EN (2001) J Am Chem Soc 123:7194

    CAS  Google Scholar 

  118. Mas-Ballesté R, Que L Jr (2007) J Am Chem Soc 129:15964

    Google Scholar 

  119. Mas-Ballesté R, Fujita M, Que L Jr (2008) Dalton Trans 37:1828

    Google Scholar 

  120. Chen MS, White MC (2007) Science 318:783

    CAS  Google Scholar 

  121. Chen MS, White MC (2010) Science 327:566

    CAS  Google Scholar 

  122. England J, Gondhia R, Bigorra-Lopez L, Petersen AR, White AJP, Britovsek GJP (2009) Dalton Trans 38:5319

    Google Scholar 

  123. England J, Davis CR, Banaru M, White AJP, Britovsek GJP (2008) Adv Synth Catal 350:883

    CAS  Google Scholar 

  124. Suzuki K, Oldenburg PD, Que L Jr (2008) Angew Chem Int Ed Engl 47:1887

    CAS  Google Scholar 

  125. Canta M, Font D, Gómez L, Ribas X, Costas M (2014) Adv Synth Catal 356:818

    CAS  Google Scholar 

  126. Vermeulen NA, Chen MS, Christina White M (2009) Tetrahedron 65:3078

    CAS  Google Scholar 

  127. Kurtz DM Jr (1990) Chem Rev 90:585

    CAS  Google Scholar 

  128. Poussereau S, Blondin G, Cesario M, Guilhem J, Chottard G, Gonnet F, Girerd J-J (1998) Inorg Chem 37:3127

    CAS  Google Scholar 

  129. Taktak S, Kryatov SV, Rybak-Akimova EV (2004) Inorg Chem 43:7196

    CAS  Google Scholar 

  130. Hazell R, Jensen KB, McKenzie CJ, Toftlund H (1995) J Chem Soc Dalton Trans: 707

    Google Scholar 

  131. Gómez L, Canta M, Font D, Prat I, Ribas X, Costas M (2013) J Org Chem 78:1421

    Google Scholar 

  132. Gormisky PE, White MC (2013) J Am Chem Soc 135:14052

    CAS  Google Scholar 

  133. Britovsek GJP, England J, White AJP (2006) Dalton Trans 35:1399

    Google Scholar 

  134. Grau M, Kyriacou A, Cabedo Martinez F, de Wispelaere I, White AJP, Britovsek GJP (2014) Dalton Trans 43:17108

    CAS  Google Scholar 

  135. Whiteoak CJ, Torres Martin de Rosales R, White AJP, Britovsek GJP (2010) Inorg Chem 49:11106

    CAS  Google Scholar 

  136. Roelfes G, Lubben M, Hage R, Que L Jr, Feringa BL (2000) Chem Eur J 6:2152

    CAS  Google Scholar 

  137. Rowland JM, Olmstead M, Mascharak PK (2001) Inorg Chem 40:2810

    CAS  Google Scholar 

  138. Wada A, Ogo S, Nagatomo S, Kitagawa T, Watanabe Y, Jitsukawa K, Masuda H (2002) Inorg Chem 41:616

    CAS  Google Scholar 

  139. Comba P, Maurer M, Vadivelu P (2009) Inorg Chem 48:10389

    CAS  Google Scholar 

  140. Wong E, Jeck J, Grau M, White AJP, Britovsek GJP (2013) Catal Sci Technol 3:1116

    CAS  Google Scholar 

  141. Roelfes G, Lubben M, Chen K, Ho RYN, Meetsma A, Genseberger S, Hermant RM, Hage R, Mandal SK, Young VG, Zang Y, Kooijman H, Spek AL, Que L Jr, Feringa BL (1999) Inorg Chem 38:1929

    CAS  Google Scholar 

  142. Lehnert N, Neese F, Ho RYN, Que L Jr, Solomon EI (2002) J Am Chem Soc 124:10810

    CAS  Google Scholar 

  143. Kaizer J, Klinker EJ, Oh NY, Rohde JU, Song WJ, Stubna A, Kim J, Muenck E, Nam W, Que L Jr (2004) J Am Chem Soc 126:472

    CAS  Google Scholar 

  144. Bukowski MR, Zhu S, Koehntop KD, Brennessel WW, Que L Jr (2004) J Biol Inorg Chem 9:39

    CAS  Google Scholar 

  145. Taktak S, Ye W, Herrera AM, Rybak-Akimova EV (2007) Inorg Chem 46:2929

    CAS  Google Scholar 

  146. Sheu C, Richert SA, Cofre P, Ross B, Sobkowiak A, Sawyer DT, Kanofsky JR (1990) J Am Chem Soc 112:1936

    CAS  Google Scholar 

  147. Tanase S, Foltz C, Gelder R d, Hage R, Bouwman E, Reedijk J (2005) J Mol Catal A Chem 225:161

    CAS  Google Scholar 

  148. Yoon J, Wilson SA, Jang YK, Seo MS, Nehru K, Hedman B, Hodgson KO, Bill E, Solomon EI, Nam W (2009) Angew Chem Int Ed 48:1257

    CAS  Google Scholar 

  149. Lyakin OY, Bryliakov KP, Talsi EP (2011) Inorg Chem 50:5526

    CAS  Google Scholar 

  150. Girerd J-J, Banse F, Simaan AJ (2000) Metal-oxo and Metal-peroxo species in catalytic oxidations, vol 97. Springer, Berlin, p 145

    Google Scholar 

  151. Balland V, Banse F, Anxolabéhère-Mallart E, Nierlich M, Girerd J-J (2003) Eur J Inorg Chem: 2529

    Google Scholar 

  152. Balland V, Mathieu D, Pons-Y-Moll N, Bartoli JF, Banse F, Battioni P, Girerd J-J, Mansuy D (2004) J Mol Catal A Chem 215:81

    CAS  Google Scholar 

  153. Buxton GV, Greenstock CL, Helman PW, Ross AB, Tsang W (1988) J Phys Chem Ref Data 17:513

    CAS  Google Scholar 

  154. MacFaul PA, Ingold KU, Wayner DDM, Que L Jr (1997) J Am Chem Soc 119:10594

    CAS  Google Scholar 

  155. Groves JT, Nemo TE (1983) J Am Chem Soc 105:6243

    CAS  Google Scholar 

  156. Lubben M, Meetsma A, Wilkinson EC, Feringa BL, Que L Jr (1995) Angew Chem Int Ed 34:1512

    CAS  Google Scholar 

  157. Kim J, Harrison RG, Kim C, Que L Jr (1996) J Am Chem Soc 118:4373

    CAS  Google Scholar 

  158. Zang Y, Kim J, Dong Y, Wilkinson EC, Appelman EH, Que L Jr (1997) J Am Chem Soc 119:4197

    CAS  Google Scholar 

  159. Lehnert N, Ho RYN, Que L Jr, Solomon EI (2001) J Am Chem Soc 123:12802

    CAS  Google Scholar 

  160. Lehnert N, Ho RYN, Que L Jr, Solomon EI (2001) J Am Chem Soc 123:8271

    CAS  Google Scholar 

  161. Lim MH, Rohde J-U, Stubna A, Bukowski MR, Costas M, Ho RYN, Muenck E, Nam W, Que L Jr (2003) Proc Natl Acad Sci U S A 100:3665

    CAS  Google Scholar 

  162. Duban EA, Bryliakov KP, Talsi EP (2007) Eur J Inorg Chem: 852

    Google Scholar 

  163. Lobanova MV, Bryliakov KP, Duban EA, Talsi EP (2003) Mendeleev Commun 13:175

    Google Scholar 

  164. Duban EA, Bryliakov KP, Talsi EP (2005) Mendeleev Commun 15:12

    Google Scholar 

  165. Park MJ, Lee J, Suh Y, Kim J, Nam W (2006) J Am Chem Soc 128:2630

    CAS  Google Scholar 

  166. Makhlynets OV, Rybak-Akimova EV (2010) Chem Eur J 16:13995

    CAS  Google Scholar 

  167. Que L Jr, Tolman WB (2008) Nature 455:333

    CAS  Google Scholar 

  168. Lyakin OY, Bryliakov KP, Britovsek GJP, Talsi EP (2009) J Am Chem Soc 131:10798

    CAS  Google Scholar 

  169. Fenton HJH (1876) Chem News: 190

    Google Scholar 

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Grau, M., Britovsek, G.J.P. (2015). High-Valent Iron in Biomimetic Alkane Oxidation Catalysis. In: Bauer, E. (eds) Iron Catalysis II. Topics in Organometallic Chemistry, vol 50. Springer, Cham. https://doi.org/10.1007/3418_2015_100

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