Fe–H Complexes in Catalysis

  • Hiroshi Nakazawa
  • Masumi Itazaki
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 33)


Organic syntheses catalyzed by iron complexes have attracted considerable attention because iron is an abundant, inexpensive, and environmentally benign metal. It has been documented that various iron hydride complexes play important roles in catalytic cycles such as hydrogenation, hydrosilylation, hydroboration, hydrogen generation, and element–element bond formation. This chapter summarizes the recent developments, mainly from 2000 to 2009, of iron catalysts involving hydride ligand(s) and the role of Fe–H species in catalytic cycles.


Catalysis Electrochemical reduction Hydroboration Hydrogenation Hydrosilylation Iron hydride complex Photochemical reduction 



We would like to show our respect for the great efforts of all authors, whose names were listed in the references. We wish to thank Dr. Yuji Suzaki for the reference collection.


  1. 1.
    Connelly NG, Damhus T, Hartshorn RM, Hutton AT (eds) (2005) Nomenclature of Inorganic Chemistry IUPAC Recommendations 2005Google Scholar
  2. 2.
    Hieber W, Leutert F (1931) Naturwissenschaften 19:360Google Scholar
  3. 3.
    Weichselfelder T, Thiede B (1926) Justus Liebigs Ann Chem 447:64Google Scholar
  4. 4.
    Dahl LF, Blount JF (1965) Inorg Chem 4:1373Google Scholar
  5. 5.
    Manojlović-Muir L, Muir KW, Ibers JA (1970) Inorg Chem 9:447Google Scholar
  6. 6.
    Guggenberger LJ, Titus DD, Flood MT, Marsh RE, Orio AA, Gray HB (1972) J Am Chem Soc 94:1135Google Scholar
  7. 7.
    Esteruelas MA, Oro LA (1998) Chem Rev 98:577Google Scholar
  8. 8.
    Morris RH, Sawyer JF, Shiralian M, Zubkowski JD (1985) J Am Chem Soc 107:5581Google Scholar
  9. 9.
    Bianchini C, Peruzzini M, Zanobini F (1988) J Organomet Chem 354:C19Google Scholar
  10. 10.
    Field LD, Messerle BA, Smernik RJ (1997) Inorg Chem 36:5984Google Scholar
  11. 11.
    Stoppioni P, Mani F, Sacconi L (1974) Inorg Chim Acta 11:227Google Scholar
  12. 12.
    Plietker B (ed) (2008) Iron catalysis in organic chemistry, Wiley-VCH, WeinheimGoogle Scholar
  13. 13.
    Bolm C, Legros J, Le Paih J, Zani L (2004) Chem Rev 104:6217Google Scholar
  14. 14.
    Fürstner A, Martin R (2005) Chem Lett 34:624Google Scholar
  15. 15.
    Correa A, Mancheño OG, Bolm C (2008) Chem Soc Rev 37:1108Google Scholar
  16. 16.
    Sherry BD, Fürstner A (2008) Acc Chem Res 41:1500Google Scholar
  17. 17.
    Gaillard S, Renaud J-L (2008) ChemSusChem 1:505Google Scholar
  18. 18.
    Enthaler S, Junge K, Beller M (2008) Angew Chem 120:3363, Angew Chem Int Ed 47:3317Google Scholar
  19. 19.
    Sarhan AAO, Bolm C (2009) Chem Soc Rev 38:2730Google Scholar
  20. 20.
    Chen MS, White MC (2007) Science 318:783Google Scholar
  21. 21.
    Frankel EN, Emken EA, Peters HM, Davison VL, Butterfield RO (1964) J Org Chem 29:3292Google Scholar
  22. 22.
    Frankel EN, Emken EA, Davison VL (1965) J Org Chem 30:2739Google Scholar
  23. 23.
    Harmon RE, Gupta SK, Brown DJ (1973) Chem Rev 73:21Google Scholar
  24. 24.
    Schroder MA, Wrighton MS (1976) J Am Chem Soc 98:551Google Scholar
  25. 25.
    Kismartoni LC, Weitz E, Cedeno DL (2005) Organometallics 24:4714Google Scholar
  26. 26.
    Daida EJ, Peters JC (2004) Inorg Chem 43:7474Google Scholar
  27. 27.
    Bart SC, Lobkovsky E, Chirik PJ (2004) J Am Chem Soc 126:13794Google Scholar
  28. 28.
    Bart SC, Chlopek K, Bill E, Bouwkamp MW, Lobkovsky E, Neese F, Wieghardt K, Chirik PJ (2006) J Am Chem Soc 128:13901Google Scholar
  29. 29.
    Bart SC, Hawrelak EJ, Lobkovsky E, Chirik PJ (2005) Organometallics 24:5518Google Scholar
  30. 30.
    Trovitch RJ, Lobkovsky E, Bill E, Chirik PJ (2008) Organometallics 27:1470Google Scholar
  31. 31.
    Archer AM, Bouwkamp MW, Cortez M-P, Lobkovsky E, Chirik PJ (2006) Organometallics 25:4269Google Scholar
  32. 32.
    Noyori R, Ohkuma T (2001) Angew Chem Int Ed 40:40Google Scholar
  33. 33.
    Ikariya T, Murata K, Noyori R (2006) Org Biomol Chem 4:393Google Scholar
  34. 34.
    Shvo Y, Czarkie D, Rahamim Y, Chodosh DF (1986) J Am Chem Soc 108:7400Google Scholar
  35. 35.
    Casey CP, Singer SW, Powell DR, Hayashi RK, Kavana M (2001) J Am Chem Soc 123:1090Google Scholar
  36. 36.
    Santosh Laxmi YR, Bäckvall J-E (2000) Chem Commun 611Google Scholar
  37. 37.
    Lau CP, Ng SM, Jia G, Lin Z (2007) Coord Chem Rev 251:2223Google Scholar
  38. 38.
    Noyori R, Kitamura M, Ohkuma T (2004) Proc Natl Acad Sci USA 101:5356Google Scholar
  39. 39.
    Clapham SE, Hadzovic A, Morris RH (2004) Coord Chem Rev 248:2201Google Scholar
  40. 40.
    Conley BL, Pennington-Boggio MK, Boz E, Williams TJ (2010) Chem Rev 110:2294Google Scholar
  41. 41.
    Blum Y, Czarkie D, Rahamim Y, Shvo Y (1985) Organometallics 4:1459Google Scholar
  42. 42.
    Shvo Y, Czarkie D, Rahamim Y, Chodosh DF (1986) J Am Chem Soc 108:7400Google Scholar
  43. 43.
    Menashe N, Shvo Y (1991) Organometallics 10:3885Google Scholar
  44. 44.
    Menashe N, Salant E, Shvo Y (1996) J Organomet Chem 514:97Google Scholar
  45. 45.
    Noyori R, Ohkuma T (1999) Pure Appl Chem 71:1493Google Scholar
  46. 46.
    Doucet H, Ohkuma T, Murata K, Yokozama T, Kozawa M, Katayama E, England AF, Ikariya T, Noyori R (1998) Angew Chem Int Ed 37:1703Google Scholar
  47. 47.
    Casey CP, Guan H (2007) J Am Chem Soc 129:5816Google Scholar
  48. 48.
    Casey CP, Guan H (2009) J Am Chem Soc 131:2499Google Scholar
  49. 49.
    Sui-Seng C, Freutel F, Lough AJ, Morris RH (2008) Angew Chem Int Ed 47:940Google Scholar
  50. 50.
    Hashiguchi S, Fujii A, Takehara J, Ikariya T, Noyori R (1995) J Am Chem Soc 117:7562Google Scholar
  51. 51.
    Rautenstrauch V, Hoang-Cong X, Churlaud R, Abdur-Rashid K, Morris RH (2003) Chem Eur J 9:4954Google Scholar
  52. 52.
    Mikhailine A, Lough AJ, Morris RH (2009) J Am Chem Soc 131:1394Google Scholar
  53. 53.
    Enthaler S, Erre G, Tse MK, Junge K, Beller M (2006) Tetrahedron Lett 47:8095Google Scholar
  54. 54.
    Enthaler S, Hagemann B, Erre G, Junge K, Beller M (2006) Chem Asian J 1:598Google Scholar
  55. 55.
    Zassinovich G, Mestroni G, Gladiali S (1992) Chem Rev 92:1051Google Scholar
  56. 56.
    Gladiali S, Mestroni G (2004) In: Beller M, Bolm C (eds) Transition metals for organic synthesis, 2nd edn. Wiley-VCH, Weinheim, p 145Google Scholar
  57. 57.
    Gladiali S, Alberico E (2006) Chem Soc Rev 35:226Google Scholar
  58. 58.
    Thorson MK, Klinkel KL, Wang J, Williams TJ (2009) Eur J Inorg Chem 295Google Scholar
  59. 59.
    Ojima I (1989) In: Patai S, Rapport Z (eds) The chemistry of organosilicon compounds, Wiley, New YorkGoogle Scholar
  60. 60.
    Brook MA (2000) Silicon in organic, organometallic, and polymer chemistry. Wiley, New YorkGoogle Scholar
  61. 61.
    Marciniec B (ed) (1992) Comprehensive handbook on hydrosilylation. Pergamon, OxfordGoogle Scholar
  62. 62.
    Marciniec B (1996) In: Cornils B, Herrmann WA (eds) Applied homogeneous catalysis with organometallic compounds, vol 1. Weinheim, Wiley-VCH, Chap 2Google Scholar
  63. 63.
    Speier JL (1979) Adv Organomet Chem 17:407Google Scholar
  64. 64.
    Marciniec B, Guliñski J (1993) J Organomet Chem 446:15Google Scholar
  65. 65.
    Nishiyama H, Furuta A (2007) Chem Commun 760Google Scholar
  66. 66.
    Furuta A, Nishiyama H (2008) Tetrahedron Lett 49:110Google Scholar
  67. 67.
    Shaikh NS, Junge K, Beller M (2007) Org Lett 9:5429Google Scholar
  68. 68.
    Shaikh NS, Enthaler S, Junge K, Beller M (2008) Angew Chem Int Ed 47:2497Google Scholar
  69. 69.
    Nishibayashi Y, Takei I, Uemura S, Hidai M (1998) Organometallics 17:3420Google Scholar
  70. 70.
    Yun J, Buchwald SL (1999) J Am Chem Soc 121:5640Google Scholar
  71. 71.
    Langlotz BK, Wadepohl H, Gade LH (2008) Angew Chem Int Ed 47:4670Google Scholar
  72. 72.
    Tondreau AM, Lobkovsky E, Chirik PJ (2008) Org Lett 10:2789Google Scholar
  73. 73.
    Tondreau AM, Darmon JM, Wile BM, Floyd SK, Lobkovsky E, Chirik PJ (2009) Organometallics 28:3928Google Scholar
  74. 74.
    Brown HC, Zaidlewicz M (2001) In: Organic Syntheses via Boranes, Vol 2. Aldrich Chemical Company, Milwaukee, p 118Google Scholar
  75. 75.
    Yamamoto Y, Asao N (1993) Chem Rev 93:2207Google Scholar
  76. 76.
    Bubnov YN (1987) Pure Appl Chem 59:895Google Scholar
  77. 77.
    Brown HC, Zaidlewicz M (2001) Organic syntheses via boranes, Vol 2. Aldrich Chemical Company, Milwaukee, WI, pp 189 and 207Google Scholar
  78. 78.
    Kennedy JWJ, Hall DG (2003) Angew Chem Int Ed 42:4732Google Scholar
  79. 79.
    Sugiura M, Hirano K, Kobayashi S (2004) J Am Chem Soc 126:7182Google Scholar
  80. 80.
    Solin N, Wallner OA, Szabó KJ (2005) Org Lett 7:689Google Scholar
  81. 81.
    Lou S, Moquist PN, Schaus SE (2007) J Am Chem Soc 129:15398Google Scholar
  82. 82.
    Sebelius S, Olsson VJ, Wallner OA, Szabó KJ (2006) J Am Chem Soc 128:8150Google Scholar
  83. 83.
    Burgess K, Ohlmeyer MJ (1991) Chem Rev 91:1179Google Scholar
  84. 84.
    Beletskaya I, Pelter A (1997) Tetrahedron 53:4957Google Scholar
  85. 85.
    Satoh M, Nomoto Y, Miyaura N, Suzuki A (1989) Tetrahedron Lett 30:3789Google Scholar
  86. 86.
    Zaidlewicz M, Meller J (1997) Tetrahedron Lett 38:7279Google Scholar
  87. 87.
    Matsumoto Y, Hayashi T (1991) Tetrahedron Lett 32:3387Google Scholar
  88. 88.
    Wu JY, Moreau B, Ritter T (2009) J Am Chem Soc 131:12915Google Scholar
  89. 89.
    Suginome M, Ohmori Y, Ito Y (2000) J Organomet Chem 611:403Google Scholar
  90. 90.
    Nakamura M, Matsuo K, Ito S, Nakamura E (2004) J Am Chem Soc 126:3686Google Scholar
  91. 91.
    Sapountzis I, Lin W, Kofink CC, Despotopoulou C, Knochel P (2005) Angew Chem 117:1682, Angew Chem Int Ed 44:1654Google Scholar
  92. 92.
    Plietker B (2006) Angew Chem 118:6200, Angew Chem Int Ed 45:6053Google Scholar
  93. 93.
    Cahiez G, Habiak V, Duplais C, Moyeux A (2007) Angew Chem 119:4442, Angew Chem Int Ed 46:4364Google Scholar
  94. 94.
    Guérinot A, Reymond S, Cossy J (2007) Angew Chem 119:6641, Angew Chem Int Ed 46:6521Google Scholar
  95. 95.
    Fürstner A, Martin R, Krause H, Seidel G, Goddard R, Lehmann CW (2008) J Am Chem Soc 130:8773Google Scholar
  96. 96.
    Carril M, Correa A, Bolm C (2008) Angew Chem 120:4940, Angew Chem Int Ed 47:4862Google Scholar
  97. 97.
    Czaplik WM, Mayer M, Wangelin AJ (2009) Angew Chem 121:616, Angew Chem Int Ed 48:607Google Scholar
  98. 98.
    Yoshikai N, Matsumoto A, Norinder J, Nakamura E (2009) Angew Chem 121:2969, Angew Chem Int Ed 48:2925Google Scholar
  99. 99.
    Cahiez G, Foulgoc L, Moyeux A (2009) Angew Chem 121:3013, Angew Chem Int Ed 48:2969Google Scholar
  100. 100.
    Li Y-Z, Li B-J, Lu X-Y, Lin S, Shi Z-J (2009) Angew Chem 121:3875, Angew Chem Int Ed 48:3817Google Scholar
  101. 101.
    Li Z, Cao L, Li C-J (2007) Angew Chem 119:6625, Angew Chem Int Ed 46:6505Google Scholar
  102. 102.
    Li Z, Yu R, Li H (2008) Angew Chem 120:7607, Angew Chem Int Ed 47:7497Google Scholar
  103. 103.
    Zhang Y, Li C-J (2007) Eur J Org Chem 4654Google Scholar
  104. 104.
    Nagano T, Hayashi T (2004) Org Lett 6:1297Google Scholar
  105. 105.
    Zhang D, Ready JM (2006) J Am Chem Soc 128:15050Google Scholar
  106. 106.
    Duboudin JG, Jousseaume B, Bonakdar A, Saux A (1979) J Organomet Chem 168:227Google Scholar
  107. 107.
    Lu Z, Ma S (2006) J Org Chem 71:2655Google Scholar
  108. 108.
    Moreau B, Wu JY, Ritter T (2009) Org Lett 11:337Google Scholar
  109. 109.
    Zhang S-Y, Tu Y-Q, Fan C-A, Zhang F-M, Shi L (2009) Angew Chem Int Ed 48:8761Google Scholar
  110. 110.
    Driller KM, Klein H, Jackstell R, Beller M (2009) Angew Chem Int Ed 48:6041Google Scholar
  111. 111.
    Periasamy M, Rameshkumar C, Radhakrishnan U (1997) Tetrahedron Lett 38:7229Google Scholar
  112. 112.
    Periasamy M, Rameshkumar C, Radhakrishnan U, Brunet J-J (1998) J Org Chem 63:4930Google Scholar
  113. 113.
    Rameshkumar C, Periasamy M (2000) Organometallics 19:2400Google Scholar
  114. 114.
    Rameshkumar C, Periasamy M (2000) Tetrahedron Lett 41:2719Google Scholar
  115. 115.
    Periasamy M, Mukkanti A, Raj DS (2004) Organometallics 23:6323Google Scholar
  116. 116.
    Periasamy M, Mukkanti A, Raj DS (2004) Organometallics 23:619Google Scholar
  117. 117.
    Rameshkumar C, Periasamy M (2000) Synlett 1619Google Scholar
  118. 118.
    Periasamy M, Rameshkumar C, Mukkati A (2002) J Organomet Chem 649:209Google Scholar
  119. 119.
    Sylvester KT, Chirik PJ (2009) J Am Chem Soc 131:8772Google Scholar
  120. 120.
    Jang H-Y, Krische MJ (2004) Acc Chem Res 37:653Google Scholar
  121. 121.
    Small BL, Brookhart M, Bennett AMA (1998) J Am Chem Soc 120:4049Google Scholar
  122. 122.
    Small BL, Brookhart M (1998) J Am Chem Soc 120:7143Google Scholar
  123. 123.
    Britovsek GJP, Gibson VC, Kimberley BS, Maddox PJ, McTavish SJ, Solan GA, Whitea AJP, Williams DJ (1998) Chem Commun 849Google Scholar
  124. 124.
    Britovsek GJP, Bruce M, Gibson VC, Kimberley BS, Maddox PJ, Mastroianni S, McTavish SJ, Redshaw C, Solan GA, Strömberg S, White AJP, Williams DJ (1999) J Am Chem Soc 121:8728Google Scholar
  125. 125.
    Britovsek GJP, Mastroianni S, Solan GA, Baugh SPD, Redshaw C, Gibson VC, White AJP, Williams DJ, Elsegood MRJ (2000) Chem Eur J 6:2221Google Scholar
  126. 126.
    Small BL, Marcucci AJ (2001) Organometallics 20:5738Google Scholar
  127. 127.
    Babik ST, Fink G (2002) J Mol Cat A: Chem 188:245Google Scholar
  128. 128.
    Khoroshun DV, Musaev DG, Vreven T, Morokuma K (2001) Organometallics 20:2007Google Scholar
  129. 129.
    Raucoules R, de Bruin T, Raybaud P, Adamo C (2009) Organometallics 28:5358Google Scholar
  130. 130.
    Kadyrov R, Riermeier TH (2003) Angew Chem 115:5630, Angew Chem Int Ed 42:5472Google Scholar
  131. 131.
    Bunlaksananusorn T, Rampf F (2005) Synlett 2682Google Scholar
  132. 132.
    Hamid MHSA, Williams JMJ (2007) Chem Commun 725Google Scholar
  133. 133.
    Tararov VI, Börner A (2005) Synlett 203Google Scholar
  134. 134.
    Tararov VI, Kadyrov R, Riermeier TH, Fischer C, Börner A (2004) Adv Synth Catal 346:561Google Scholar
  135. 135.
    Tararov VI, Kadyrov R, Riermeier TH, Börner A (2002) Adv Synth Catal 344:200Google Scholar
  136. 136.
    Tararov VI, Kadyrov R, Riermeier TH, Börner A (2000) Chem Commun 1867Google Scholar
  137. 137.
    Kadyrov R, Riermeier TH, Dingerdissen U, Tararov V, Börner A (2003) J Org Chem 68:4067Google Scholar
  138. 138.
    Kitamura M, Lee D, Hayashi S, Tanaka S, Yoshimura M (2002) J Org Chem 67:8685Google Scholar
  139. 139.
    Imao D, Fujihara S, Yamamoto T, Ohta T, Ito Y (2005) Tetrahedron 61:6988Google Scholar
  140. 140.
    Fujita K-I, Yamaguchi R (2005) Synlett 560Google Scholar
  141. 141.
    Chi Y, Zhou Y-G, Zhang X (2003) J Org Chem 68:4120Google Scholar
  142. 142.
    Blank B, Madalska M, Kempe R (2008) Adv Synth Catal 350:749Google Scholar
  143. 143.
    Robichaud A, Nait Ajjou A (2006) Tetrahedron Lett 47:3633Google Scholar
  144. 144.
    Bhor MD, Bhanushali MJ, Nandurkar NS, Bhanage BM (2008) Tetrahedron Lett 49:965Google Scholar
  145. 145.
    Zhou S, Addis D, Das S, Junge K, Beller M (2009) Chem Commun 4883Google Scholar
  146. 146.
    Hanada S, Motoyama Y, Nagashima H (2008) Eur J Org Chem 4097Google Scholar
  147. 147.
    Zhou S, Junge K, Addis D, Das S, Beller M (2009) Angew Chem Int Ed 48:9507Google Scholar
  148. 148.
    Sunada Y, Kawakami H, Imaoka T, Motoyama Y, Nagashima H (2009) Angew Chem Int Ed 48:9511Google Scholar
  149. 149.
    Iwanami K, Seo H, Tobita Y, Oriyama T (2005) Synthesis 183Google Scholar
  150. 150.
    Iwanami K, Yano K, Oriyama T (2005) Synthesis 2669Google Scholar
  151. 151.
    Iwanami K, Yano K, Oriyama T (2007) Chem Lett 36:38Google Scholar
  152. 152.
    Doyle MP, DeBruyn DJ, Kooistra DA (1972) J Am Chem Soc 94:3659Google Scholar
  153. 153.
    Nicolaou KC, Hwang C-K, Nugiel DA (1989) J Am Chem Soc 111:4136Google Scholar
  154. 154.
    Izumi M, Fukase K (2005) Chem Lett 34:594Google Scholar
  155. 155.
    Kato J-I, Iwasawa N, Mukaiyama T (1985) Chem Lett 743Google Scholar
  156. 156.
    Sassaman MB, Kotian KD, Prakash GKS, Olah GA (1987) J Org Chem 52:4314Google Scholar
  157. 157.
    Hatakeyama S, Mori H, Kitano K, Yamada H, Nishizawa M (1994) Tetrahedron Lett 35:4367Google Scholar
  158. 158.
    Komatsu N, Ishida J, Suzuki H (1997) Tetrahedron Lett 38:7219Google Scholar
  159. 159.
    Bajwa JS, Jiang X, Slade J, Prasad K, Repič O, Blacklock TJ (2002) Tetrahedron Lett 43:6709Google Scholar
  160. 160.
    Yang W-C, Lu X-A, Kulkarni SS, Hung S-C (2003) Tetrahedron Lett 44:7837Google Scholar
  161. 161.
    Chandrasekhar S, Chandrashekar G, Babu BN, Vijeender K, Venkatram Reddy K (2004) Tetrahedron Lett 45:5497Google Scholar
  162. 162.
    Wada M, Nagayama S, Mizutani K, Hiroi R, Miyoshi N (2002) Chem Lett 248Google Scholar
  163. 163.
    Nakazawa H, Kamata K, Itazaki M (2005) Chem Commun 4004Google Scholar
  164. 164.
    Nakazawa H, Itazaki M, Kamata K, Ueda K (2007) Chem Asian J 2:882Google Scholar
  165. 165.
    Nakazawa H, Kawasaki T, Miyoshi K, Suresh CH, Koga N (2004) Organometallics 23:117Google Scholar
  166. 166.
    Itazaki M, Ueda K, Nakazawa H (2009) Angew Chem Int Ed 48:3313; ibid 48: 6938Google Scholar
  167. 167.
    Sharma HK, Pannell KH (2009) Angew Chem Int Ed 48:7052Google Scholar
  168. 168.
    Trost BM, Kulawiec RJ (1993) J Am Chem Soc 115:2027 (and references cited therein)Google Scholar
  169. 169.
    Bäckvall JE, Andreasson U (1993) Tetrahedron Lett 34:5459Google Scholar
  170. 170.
    Marko IE, Gautier A, Tsukazaki M, Llobet A, Plantalech-Mir E, Urch CJ, Brown SM (1999) Angew Chem Int Ed 38:1960Google Scholar
  171. 171.
    Slugovc C, Rüba E, Schmid R, Kirchner K (1999) Organometallics 18:4230Google Scholar
  172. 172.
    Ni Bricourt H, Monflier E, Carpentier J-F, Mortreux A (1998) Eur J Inorg Chem 1739Google Scholar
  173. 173.
    Cherkaoui H, Soufiaoui M, Grée R (2001) Tetrahedron 57:2379Google Scholar
  174. 174.
    Hendrix WT, Cowherd FG, von Rosenberg JL (1968) Chem Commun 97Google Scholar
  175. 175.
    Strauss JU, Ford PW (1975) Tetrahedron Lett 2917Google Scholar
  176. 176.
    Chong TS, Tan ST, Fan WY (2006) Chem A Eur J 12:5128Google Scholar
  177. 177.
    Shi B, O’Brien RJ, Bao S, Davis BH (2001) J Catal 199:202Google Scholar
  178. 178.
    Taber DF, Kanai K, Jiang Q, Bui G (2000) J Am Chem Soc 122:6807Google Scholar
  179. 179.
    Glascoe EA, Sawyer KR, Shanoski JE, Harris CB (2007) J Phys Chem C 111:8789Google Scholar
  180. 180.
    Sawyer KR, Glascoe EA, Cahoon JF, Schlegel JP, Harris CB (2008) Organometallics 27:4370Google Scholar
  181. 181.
    Navarro RM, Pena MA, Fierro JLG (2007) Chem Rev 107:3952Google Scholar
  182. 182.
    Peters JW, Lanzilotta WN, Lemon BJ, Seefeldt LC (1998) Science 282:1853Google Scholar
  183. 183.
    Nicolet Y, de Lacey AL, Vernede X, Fernandez VM, Hatchikian EC, Fontecilla-Camps JC (2001) J Am Chem Soc 123:1596Google Scholar
  184. 184.
    Nicolet Y, Piras C, Legrand P, Hatchikian CE, Fontecilla-Camps JC (1999) Structure 7:13Google Scholar
  185. 185.
    Peters JW, Lanzilotta WN, Lemon BJ, Seefeldt LC (1998) Science 282:1853Google Scholar
  186. 186.
    Nicolet Y, de Lacey AL, Vernede X, Fernandez VM, Hatchikian EC, Fontecilla-Camps JC (2001) J Am Chem Soc 123:1596Google Scholar
  187. 187.
    Frey M (2002) Chembiochem 3:153Google Scholar
  188. 188.
    Volbeda A, Garcin E, Piras C, de Lacey AL, Fernandez VM, Hatchikian EC, Frey M, Fontecilla-Camps JC (1996) J Am Chem Soc 118:12989Google Scholar
  189. 189.
    Volbeda A, Charon M-H, Piras C, Hatchikian EC, Frey M, Fontecilla-Camps JC (1995) Nature 373:580Google Scholar
  190. 190.
    Volbeda A, Martin L, Cavazza C, Matho M, Faber BW, Roseboom W, Albracht SPJ, Garcin E, Rousset M, Fontecilla-Camps JC (2005) J Biol Inorg Chem 10:239Google Scholar
  191. 191.
    Ogata H, Hirota S, Nakahara A, Komori H, Shibata N, Kato T, Kano K, Higuchi Y (2005) Structure 13:1635Google Scholar
  192. 192.
    de Lacey AL, Fernandez VM, Rousset M (2005) Coord Chem Rev 249:1596Google Scholar
  193. 193.
    Vincent KA, Belsey NA, Lubitz W, Armstrong FA (2006) J Am Chem Soc 128:7448Google Scholar
  194. 194.
    Huhmann-Vincent J, Scott BL, Kubas GJ (1999) Inorg Chim Acta 294:240Google Scholar
  195. 195.
    Shima S, Pilak O, Vogt S, Schick M, Stagni MS, Meyer-Klaucke W, Warkentin E, Thauer RK, Ermler U (2008) Science 321:572Google Scholar
  196. 196.
    Gloaguen F, Lawrence JD, Rauchfuss TB (2001) J Am Chem Soc 123:9476Google Scholar
  197. 197.
    Gloaguen F, Lawrence JD, Rauchfuss TB, Bénard M, Rohmer M-M (2002) Inorg Chem 41:6573Google Scholar
  198. 198.
    Mejia-Rodriguez R, Chong D, Reibenspies JH, Soriaga MP, Darensbourg MY (2004) J Am Chem Soc 126:12004Google Scholar
  199. 199.
    Chong D, Georgakaki IP, Mejia-Rodriguez R, Sanabria-Chinchilla J, Soriaga MP, Darensbourg MY (2003) Dalton Trans 3:4158Google Scholar
  200. 200.
    Volkers PI, Rauchfuss TB (2007) J Inorg Biochem 101:1748Google Scholar
  201. 201.
    Felton GAN, Vannucci AK, Chen J, Lockett LT, Okumura N, Petro BJ, Zakai UI, Evans DH, Glass RS, Lichtenberger DL (2007) J Am Chem Soc 129:12521Google Scholar
  202. 202.
    Felton GAN, Vannucci AK, Okumura N, Lockett LT, Evans DH, Glass RS, Lichtenberger DL (2008) Organometallics 27:4671Google Scholar
  203. 203.
    Chiang M-H, Liu Y-C, Yang S-T, Lee G-H (2009) Inorg Chem 48:7604Google Scholar
  204. 204.
    Liu Z-P, Hu P (2002) J Am Chem Soc 124:5175Google Scholar
  205. 205.
    Fan H-J, Hall MB (2001) J Am Chem Soc 123:3828Google Scholar
  206. 206.
    Zampella G, Greco C, Fantucci P, De Gioia L (2006) Inorg Chem 45:4109Google Scholar
  207. 207.
    Greco C, Bruschi M, De Gioia L, Ryde U (2007) Inorg Chem 46:5911Google Scholar
  208. 208.
    Ohki Y, Yasumura K, Kuge K, Tanino S, Ando M, Li Z, Tatsumi K (2008) Proc Natl Acad Sci USA 105:7652Google Scholar
  209. 209.
    Li Z, Ohki Y, Tatsumi K (2005) J Am Chem Soc 127:8950Google Scholar
  210. 210.
    Tanino S, Li Z, Ohki Y, Tatsumi K (2009) Inorg Chem 48:2358Google Scholar
  211. 211.
    Perra A, Davies ES, Hyde JR, Wang Q, McMaster J, Schröder M (2006) Chem Commun 1103Google Scholar
  212. 212.
    Barton BE, Whaley CM, Rauchfuss TB, Gray DL (2009) J Am Chem Soc 131:6942Google Scholar
  213. 213.
    Yang X, Hall MB (2009) J Am Chem Soc 131:10901Google Scholar
  214. 214.
    Kirch M, Lehn J-M, Sauvage J-P (1979) Helv Chim Acta 62:1345Google Scholar
  215. 215.
    Moradpour A, Amouyal E, Keller P, Kagan H (1978) Nouv J Chim 2:547Google Scholar
  216. 216.
    Kalyanasundaram K, Kiwi J, Grätzel M (1978) Helv Chim Acta 61:2720Google Scholar
  217. 217.
    Krishnan CV, Sutin N (1981) J Am Chem Soc 103:2141Google Scholar
  218. 218.
    Goldsmith JI, Hudson WR, Lowry MS, Anderson TH, Bernhard S (2005) J Am Chem Soc 127:7502Google Scholar
  219. 219.
    Tinker LL, McDaniel ND, Curtin PN, Smith CK, Ireland MJ, Bernhard S (2007) Chem Eur J 13:8726Google Scholar
  220. 220.
    Cline ED, Adamson SE, Bernhard S (2008) Inorg Chem 47:10378Google Scholar
  221. 221.
    Tinker LL, Bernhard S (2009) Inorg Chem 48:10507Google Scholar
  222. 222.
    Curtin PN, Tinker LL, Burgess CM, Cline ED, Bernhard S (2009) Inorg Chem 48:10498Google Scholar
  223. 223.
    Du P, Schneider J, Luo G, Brennessel WW, Eisenberg R (2009) Inorg Chem 48:4952Google Scholar
  224. 224.
    Du P, Knowles K, Eisenberg R (2008) J Am Chem Soc 130:12576Google Scholar
  225. 225.
    Zhang J, Du P, Schneider J, Jarosz P, Eisenberg R (2007) J Am Chem Soc 129:7726Google Scholar
  226. 226.
    Lazarides T, McCormick T, Du P, Luo G, Lindley B, Eisenberg R (2009) J Am Chem Soc 131:9192Google Scholar
  227. 227.
    Rau S, Schäfer B, Gleich D, Anders E, Rudolph M, Friedrich M, Görls H, Henry W, Vos JG (2006) Angew Chem 118:6361, Angew Chem Int Ed 45:6215Google Scholar
  228. 228.
    Elvington M, Brown J, Arachchige SM, Brewer KJ (2007) J Am Chem Soc 129:10644Google Scholar
  229. 229.
    Ozawa H, Haga M, Sakai K (2006) J Am Chem Soc 128:4926Google Scholar
  230. 230.
    Palmans R, Frank AJ (1991) J Phys Chem 95:9438Google Scholar
  231. 231.
    Na Y, Wang M, Pan J, Zhang P, Åkermark B, Sun L (2008) Inorg Chem 47:2805Google Scholar
  232. 232.
    Lomoth R, Ott S (2009) Dalton Trans 9952Google Scholar
  233. 233.
    Gärtner F, Sundararaju B, Surkus A-E, Boddien A, Loges B, Junge H, Dixneuf PH, Beller M (2009) Angew Chem Int Ed 48:9962Google Scholar
  234. 234.
    Kluwer AM, Kapre R, Hartl F, Lutz M, Spek AL, Brouwer AM, van Leeuwen PWNM, Reek JNH (2009) Proc Natl Acad Sci 106:10460Google Scholar
  235. 235.
    Knölker H-J, Goesmann H, Klauss R (1999) Angew Chem Int Ed 38:702Google Scholar
  236. 236.
    Mercury 2.2 for Windows. This material is available free of charge via the Internet at

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© Springer Berlin Heidelberg 2011

Authors and Affiliations

  1. 1.Department of Chemistry, Graduate School of ScienceOsaka City UniversityOsakaJapan

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