Recent Advances in Alkane Dehydrogenation Catalyzed by Pincer Complexes

Chapter
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 54)

Abstract

Olefins are ubiquitous intermediates in the production of fuels and commodity chemicals. Accordingly, the development of methods for the selective dehydrogenation of alkanes to give olefins is a goal with great potential value. Molecular (homogeneous) catalysts appear quite promising in this respect. Great advances have been seen with pincer-ligated catalysts since the mid-1990s, particularly (but not exclusively) with iridium complexes. In this chapter we give an overview of this productive area of research, with emphasis on recent progress.

Keywords

Alkane functionalization Alkane metathesis Alkylarenes C–H bond activation Dehydrogenation Pincer catalysts 

References

  1. 1.
    Crabtree RH, Mihelcic JM, Quirk JM (1979) J Am Chem Soc 101:7738–7740CrossRefGoogle Scholar
  2. 2.
    Crabtree RH, Demou PC, Eden D, Mihelcic JM, Parnell CA, Quirk JM, Morris GE (1982) J Am Chem Soc 104:6994–7001CrossRefGoogle Scholar
  3. 3.
    Crabtree RH, Mellea MF, Mihelcic JM, Quirk JM (1982) J Am Chem Soc 104:107–113CrossRefGoogle Scholar
  4. 4.
    Baudry D, Ephritikhine M, Felkin H (1980) J Chem Soc Chem Commun 1243–1244Google Scholar
  5. 5.
    Baudry D, Ephritikhine M, Felkin H (1982) J Chem Soc Chem Commun 606–607Google Scholar
  6. 6.
    Baudry D, Ephritikhine M, Felkin H, Zakrzewski J (1982) J Chem Soc Chem Commun 1235–1236Google Scholar
  7. 7.
    Bergman RG (1984) Science 223:902–908CrossRefGoogle Scholar
  8. 8.
    Janowicz AH, Bergman RG (1982) J Am Chem Soc 104:352–354CrossRefGoogle Scholar
  9. 9.
    Janowicz AH, Bergman RG (1983) J Am Chem Soc 105:3929–3939CrossRefGoogle Scholar
  10. 10.
    Ghosh CK, Rodgers DPS, Graham WAG (1988) J Chem Soc Chem Commun 1511–12Google Scholar
  11. 11.
    Hoyano JK, Graham WAG (1982) J Am Chem Soc 104:3723–3725CrossRefGoogle Scholar
  12. 12.
    Rest AJ, Whitwell I, Graham WAG, Hoyano JK, McMaster AD (1984) J Chem Soc Chem Commun 624–626Google Scholar
  13. 13.
    Rest AJ, Whitwell I, Graham WAG, Hoyano JK, McMaster AD (1987) J Chem Soc Dalton Trans 1181Google Scholar
  14. 14.
    Harper TGP, Shinomoto RS, Deming MA, Flood TC (1988) J Am Chem Soc 110:7915–7916CrossRefGoogle Scholar
  15. 15.
    Jones WD, Feher FJ (1983) Organometallics 2:562–563CrossRefGoogle Scholar
  16. 16.
    Jones WD (2000) Science 287:1942–1943Google Scholar
  17. 17.
    Labinger JA, Bercaw JE (2002) Nature 417:507–514CrossRefGoogle Scholar
  18. 18.
    Goldberg KI, Goldman AS (eds) (2004) Activation and functionalization of C–H bonds. In: ACS symposium series 885, Washington, DC, American Chemical SocietyGoogle Scholar
  19. 19.
    Bergman RG (2007) Nature 446:506CrossRefGoogle Scholar
  20. 20.
    Crabtree RH (2010) Chem Rev 110:575CrossRefGoogle Scholar
  21. 21.
    Balcells D, Clot E, Eisenstein O (2010) Chem Rev 110:749–823CrossRefGoogle Scholar
  22. 22.
    Baudry D, Ephritikhine M, Felkin H, Holmes-Smith R (1983) J. Chem. Soc. Chem Commun 788–789Google Scholar
  23. 23.
    Goldman AS, Renkema KB, Czerw M, Krogh-Jespersen K (2004) Activation and Functionalization of C–H Bonds. ACS Symp Ser 885:198–215CrossRefGoogle Scholar
  24. 24.
    Burk MJ, Crabtree RH, Parnell CP, Uriarte RJ (1984) Organometallics 3:816–817CrossRefGoogle Scholar
  25. 25.
    Felkin H, Fillebeen-Khan T, Gault Y, Holmes-Smith R, Zakrzewski J (1984) Tetrahedron Lett 25:1279–1282CrossRefGoogle Scholar
  26. 26.
    Felkin H, Fillebeen-khan T, Holmes-Smith R, Yingrui L (1985) Tetrahedron Lett 26:1999–2000CrossRefGoogle Scholar
  27. 27.
    Afeefy, HY; Liebman, JF; Stein, SE "Neutral Thermochemical Data" in NIST Chemistry WebBook, NIST Standard Reference Database Number 69, Eds. P.J. Linstrom and W.G. Mallard, National Institute of Standards and Technology, Gaithersburg MD, 20899, http://webbook.nist.gov, (retrieved October 15, 2014)
  28. 28.
    Burk MJ, Crabtree RH, McGrath DV (1985) J. Chem. Soc. Chem Commun 1829–1830Google Scholar
  29. 29.
    Burk MJ, Crabtree RH (1987) J Am Chem Soc 109:8025–8032CrossRefGoogle Scholar
  30. 30.
    Kunin AJ, Eisenberg R (1986) J Am Chem Soc 108:535–536CrossRefGoogle Scholar
  31. 31.
    Kunin AJ, Eisenberg R (1988) Organometallics 7:2124–2129CrossRefGoogle Scholar
  32. 32.
    Sakakura T, Sodeyama T, Tanaka M (1989) New J Chem 13:737–745Google Scholar
  33. 33.
    Sakakura T, Sodeyama T, Tokunaga Y, Tanaka M (1988) Chem Lett 17:263–264CrossRefGoogle Scholar
  34. 34.
    Sakakura T, Tanaka M (1987) Chem Let 16:249–252CrossRefGoogle Scholar
  35. 35.
    Sakakura T, Tanaka M (1987) J Chem Soc Chem Commun 758–759Google Scholar
  36. 36.
    Aoki T, Crabtree RH (1993) Organometallics 12:294–298CrossRefGoogle Scholar
  37. 37.
    Fujii T, Higashino Y, Saito Y (1993) J Chem Soc Dalton Trans 517–520Google Scholar
  38. 38.
    Fujii T, Saito Y (1990) J Chem Soc Chem Commun 757–758Google Scholar
  39. 39.
    Maguire JA, Boese WT, Goldman AS (1989) J Am Chem Soc 111:7088–7093CrossRefGoogle Scholar
  40. 40.
    Maguire JA, Goldman AS (1991) J Am Chem Soc 113:6706–6708CrossRefGoogle Scholar
  41. 41.
    Maguire JA, Petrillo A, Goldman AS (1992) J Am Chem Soc 114:9492–9498CrossRefGoogle Scholar
  42. 42.
    Chowdhury AD, Weding N, Julis J, Franke R, Jackstell R, Beller M (2014) Angew Chem Int Ed Engl 53:6477–6481CrossRefGoogle Scholar
  43. 43.
    Wang K, Goldman ME, Emge TJ, Goldman AS (1996) J Organomet Chem 518:55–68CrossRefGoogle Scholar
  44. 44.
    Gupta M, Hagen C, Flesher RJ, Kaska WC, Jensen CM (1996) Chem Commun 2083–2084Google Scholar
  45. 45.
    Gupta M, Hagen C, Kaska WC, Cramer RE, Jensen CM (1997) J Am Chem Soc 119:840–841CrossRefGoogle Scholar
  46. 46.
    Choi J, Goldman A (2011) Top Organometal Chem 34:139–167Google Scholar
  47. 47.
    Choi J, MacArthur AHR, Brookhart M, Goldman AS (2011) Chem Rev 111:1761–1779CrossRefGoogle Scholar
  48. 48.
    Findlater M, Choi J, Goldman AS, Brookhart M (2012) Catal Met Complexes 38:113–141CrossRefGoogle Scholar
  49. 49.
    Xu W-W, Rosini GP, Krogh-Jespersen K, Goldman AS, Gupta M, Jensen CM, Kaska WC (1997) Chem Commun 2273–2274Google Scholar
  50. 50.
    Liu F, Pak EB, Singh B, Jensen CM, Goldman AS (1999) J Am Chem Soc 121:4086–4087CrossRefGoogle Scholar
  51. 51.
    Liu FS, Goldman A (1999) Chem Commun 655–656Google Scholar
  52. 52.
    Haenel MW, Oevers S, Angermund K, Kaska WC, Fan H-J, Hall MB (2001) Angew Chem Int Ed Engl 40:3596–3600CrossRefGoogle Scholar
  53. 53.
    Punji B, Emge TJ, Goldman AS (2010) Organometallics 29:2702–2709CrossRefGoogle Scholar
  54. 54.
    Zhu K, Achord PD, Zhang X, Krogh-Jespersen K, Goldman AS (2004) J Am Chem Soc 126:13044–13053CrossRefGoogle Scholar
  55. 55.
    Huang Z, Brookhart M, Goldman AS, Kundu S, Ray A, Scott SL, Vicente BC (2009) Adv Synth Catal 351:188–206CrossRefGoogle Scholar
  56. 56.
    Kuklin SA, Sheloumov AM, Dolgushin FM, Ezernitskaya MG, Peregudov AS, Petrovskii PV, Koridze AA (2006) Organometallics 25:5466–5476CrossRefGoogle Scholar
  57. 57.
    Bezier D, Brookhart M (2014) ACS Catal 4:3411–3420CrossRefGoogle Scholar
  58. 58.
    Göttker-Schnetmann I, Brookhart M (2004) J Am Chem Soc 126:9330–9338CrossRefGoogle Scholar
  59. 59.
    Göttker-Schnetmann I, White P, Brookhart M (2004) J Am Chem Soc 126:1804–1811CrossRefGoogle Scholar
  60. 60.
    Göttker-Schnetmann I, White PS, Brookhart M (2004) Organometallics 23:1766–1776CrossRefGoogle Scholar
  61. 61.
    Ahuja R, Punji B, Findlater M, Supplee C, Schinski W, Brookhart M, Goldman AS (2011) Nature Chem 3:167–171CrossRefGoogle Scholar
  62. 62.
    Dobereiner GE, Yuan J, Schrock RR, Goldman AS, Hackenberg JD (2013) J Am Chem Soc 135:12572–12575CrossRefGoogle Scholar
  63. 63.
    Shi Y, Suguri T, Dohi C, Yamada H, Kojima S, Yamamoto Y (2013) Chem Eur J 19:10672–10689CrossRefGoogle Scholar
  64. 64.
    Yao W, Zhang Y, Jia X, Huang Z (2014) Angew Chem 126:1414–1418CrossRefGoogle Scholar
  65. 65.
    Jia X, Zhang L, Qin C, Leng X, Huang Z (2014) Chem Commun 50:11056–11059CrossRefGoogle Scholar
  66. 66.
    Morales-Morales D, Redón Ro, Yung C, Jensen CM (2004) Inorg Chim Acta 357:2953–2956Google Scholar
  67. 67.
    Kundu S, Choliy Y, Zhuo G, Ahuja R, Emge TJ, Warmuth R, Brookhart M, Krogh-Jespersen K, Goldman AS (2009) Organometallics 28:5432–5444CrossRefGoogle Scholar
  68. 68.
    Yao W, Zhang Y, Jia X, Huang Z (2014) Angew Chem Int Ed Engl 53:1390–1394CrossRefGoogle Scholar
  69. 69.
    Brayton DF, Beaumont PR, Fukushima EY, Sartain HT, Morales-Morales D, Jensen CM (2014) Organometallics 33:5198–5202CrossRefGoogle Scholar
  70. 70.
    Jia X, Zhang L, Qin C, Leng X, Huang Z (2014) Chem Commun 50:11056–11059CrossRefGoogle Scholar
  71. 71.
    Haibach MC, Kundu S, Brookhart M, Goldman AS (2012) Acc Chem Res 45:947–958CrossRefGoogle Scholar
  72. 72.
    Goldman AS, Roy AH, Huang Z, Ahuja R, Schinski W, Brookhart M (2006) Science 312:257–261CrossRefGoogle Scholar
  73. 73.
    Ahuja R, Kundu S, Goldman AS, Brookhart M, Vicente BC, Scott SL (2008) Chem Commun 253-255Google Scholar
  74. 74.
    Nawara-Hultzsch AJ, Hackenberg JD, Punji B, Supplee C, Emge TJ, Bailey BC, Schrock RR, Brookhart M, Goldman AS (2013) ACS Catal 3:2505–2514CrossRefGoogle Scholar
  75. 75.
    Goldman A, Ahuja R, Schinski W (2013) Rutgers, The State University of New Jersey, USA. US20130123552A1Google Scholar
  76. 76.
    Steffens AM, Goldman AS (2013) Abstracts of Papers, 245th ACS National Meeting & Exposition, New Orleans, LA, United States, April 7-11, 2013, INOR-1328Google Scholar
  77. 77.
    Leitch DC, Labinger JA, Bercaw JE (2014) Organometallics 33:3353–3365CrossRefGoogle Scholar
  78. 78.
    Leitch DC, Lam YC, Labinger JA, Bercaw JE (2013) J Am Chem Soc 135:10302–10305CrossRefGoogle Scholar
  79. 79.
    Gupta M, C. Kaska W, M. Jensen C (1997) Chem Commun 461–462Google Scholar
  80. 80.
    Jensen CM (1999) Chem. Commun 2443–2449Google Scholar
  81. 81.
    Zhang X, Fried A, Knapp S, Goldman AS (2003) Chem. Commun 2060–2061Google Scholar
  82. 82.
    Kumar A, Goldman AS (2013) Abstracts of Papers, 245th ACS National Meeting & Exposition, New Orleans, LA, United States, April 7-11, 2013, INOR-1202Google Scholar
  83. 83.
    Biswas S, Huang Z, Choliy Y, Wang DY, Brookhart M, Krogh-Jespersen K, Goldman AS (2012) J Am Chem Soc 134:13276–13295CrossRefGoogle Scholar
  84. 84.
    Knapp SMM, Shaner SE, Kim D, Shopov DY, Tendler JA, Pudalov DM, Chianese AR (2014) Organometallics 33:473–484CrossRefGoogle Scholar
  85. 85.
    Roddick DM (2013) Top Organomet Chem 40:49–88Google Scholar
  86. 86.
    Adams JJ, Arulsamy N, Roddick DM (2011) Organometallics 30:697–711CrossRefGoogle Scholar
  87. 87.
    Adams JJ, Arulsamy N, Roddick DM (2011) Dalton Trans 40:10014–10019CrossRefGoogle Scholar
  88. 88.
    Adams JJ, Arulsamy N, Roddick DM (2012) Organometallics 31:1439–1447CrossRefGoogle Scholar
  89. 89.
    Lee DW, Kaska WC, Jensen CM (1998) Organometallics 17:1–3CrossRefGoogle Scholar
  90. 90.
    Ghosh R, Kanzelberger M, Emge TJ, Hall GS, Goldman AS (2006) Organometallics 25:5668–5671CrossRefGoogle Scholar
  91. 91.
    Morales-Morales D, Lee DW, Wang Z, Jensen CM (2001) Organometallics 20:1144–1147CrossRefGoogle Scholar
  92. 92.
    Allen KE, Heinekey DM, Goldman AS, Goldberg KI (2014) Organometallics 33:1337–1340CrossRefGoogle Scholar
  93. 93.
    Allen KE, Heinekey DM, Goldman AS, Goldberg KI (2013) Organometallics 32:1579–1582CrossRefGoogle Scholar
  94. 94.
    Chianese AR, Drance MJ, Jensen KH, McCollom SP, Yusufova N, Shaner SE, Shopov DY, Tendler JA (2014) Organometallics 33:457–464CrossRefGoogle Scholar
  95. 95.
    Chianese AR, Mo A, Lampland NL, Swartz RL, Bremer PT (2010) Organometallics 29:3019–3026CrossRefGoogle Scholar
  96. 96.
    Chianese AR, Shaner SE, Tendler JA, Pudalov DM, Shopov DY, Kim D, Rogers SL, Mo A (2012) Organometallics 31:7359–7367CrossRefGoogle Scholar
  97. 97.
    Ito J-i, Kaneda T, Nishiyama H (2012) Organometallics 31:4442-4449Google Scholar
  98. 98.
    Pahls DR, Allen KE, Wright AM, Goldberg KI, Cundari TR (2014) Abstracts of Papers, 248th ACS National Meeting & Exposition, San Francisco, CA, United States, August 10-14, 2014, INOR-804Google Scholar
  99. 99.
    Kuznetsov VF, Abdur-Rashid K, Lough AJ, Gusev DG (2006) J Am Chem Soc 128:14388–14396CrossRefGoogle Scholar
  100. 100.
    Azerraf C, Gelman D (2009) Organometallics 28:6578–6584CrossRefGoogle Scholar
  101. 101.
    Gelman D, Romm R (2013) Organometal Pincer Chem 40:289–317Google Scholar
  102. 102.
    Musa S, Ackermann L, Gelman D (2013) Adv Synth Catal 355:3077–3080CrossRefGoogle Scholar
  103. 103.
    Huang Z, Rolfe E, Carson EC, Brookhart M, Goldman AS, El-Khalafy SH, MacArthur AHR (2010) Adv Synth Catal 352:125–135CrossRefGoogle Scholar
  104. 104.
    Gagliardo M, Chase PA, Brouwer S, van Klink GPM, van Koten G (2007) Organometallics 26:2219–2227CrossRefGoogle Scholar
  105. 105.
    Adams JJ, Gruver BC, Donohoue R, Arulsamy N, Roddick DM (2012) Dalton Trans 41:12601–12611CrossRefGoogle Scholar
  106. 106.
    Gruver BC, Adams JJ, Arulsamy N, Roddick DM (2013) Organometallics 32:6468–6475CrossRefGoogle Scholar
  107. 107.
    Gruver BC, Adams JJ, Warner SJ, Arulsamy N, Roddick DM (2011) Organometallics 30:5133–5140CrossRefGoogle Scholar
  108. 108.
    Kerr RA (2011) Science 331:1510–1511CrossRefGoogle Scholar
  109. 109.
    Murray J, King D (2012) Nature 481:433–435CrossRefGoogle Scholar
  110. 110.
    Brandt AR, Millard-Ball A, Ganser M, Gorelick SM (2013) Environ Sci Technol 47:8031–8041CrossRefGoogle Scholar
  111. 111.
    Huber GW, Iborra S, Corma A (2006) Chem Rev 106:4044–4098CrossRefGoogle Scholar
  112. 112.
    Graves C, Ebbesen SD, Mogensen M, Lackner KS (2011) Renew Sustain Energy Rev 15:1–23CrossRefGoogle Scholar
  113. 113.
    Dry ME (2002) J Chem Technol Biotechnol 77:43–50CrossRefGoogle Scholar
  114. 114.
    Dry ME (2002) Catalysis Today 71:227–241CrossRefGoogle Scholar
  115. 115.
    Dry ME (2004) Appl Catal A 276:1–3CrossRefGoogle Scholar
  116. 116.
    Leckel D (2009) Energy Fuels 23:2342–2358CrossRefGoogle Scholar
  117. 117.
    Hildebrandt D, Glasser D, Hausberger B, Patel B, Glasser BJ (2009) Science 323:1680–1681CrossRefGoogle Scholar
  118. 118.
    Burnett RL, Hughes TR (1973) J Catal 31:55–64CrossRefGoogle Scholar
  119. 119.
    Vidal V, Théolier A, Thivolle-Cazat J, Basset J-M (1997) Science 276:99–102CrossRefGoogle Scholar
  120. 120.
    Coperet C, Maury O, Thivolle-Cazat J, Basset J-M (2001) Angew Chem Int Ed Engl 40:2331–2334CrossRefGoogle Scholar
  121. 121.
    Basset JM, Copéret C, Lefort L, Maunders BM, Maury O, Le Roux E, Saggio G, Soignier S, Soulivong D, Sunley GJ, Taoufik M, Thivolle-Cazat J (2005) J Am Chem Soc 127:8604–8605CrossRefGoogle Scholar
  122. 122.
    Biswas S, Brookhart M, Choliy Y, Goldman A, Huang Z, Krogh-Jespersen K (2010) Abstracts of Papers, 239th ACS National Meeting, San Francisco, CA, United States, March 21-25, 2010, INOR-670Google Scholar
  123. 123.
    Biswas S, Zhou T, Wang DY, Hackenberg J, Nawara-Hultzsch A, Schrock RR, Brookhart M, Krogh-Jespersen K, Goldman AS (2013) Abstracts of Papers, 245th ACS National Meeting & Exposition, New Orleans, LA, United States, April 7-11, 2013, INOR-681Google Scholar
  124. 124.
    Schrock RR (2001) Chem Rev 102:145–180CrossRefGoogle Scholar
  125. 125.
    Bailey BC, Schrock RR, Kundu S, Goldman AS, Huang Z, Brookhart M (2008) Organometallics 28:355–360CrossRefGoogle Scholar
  126. 126.
    Goldman AS, Stibrany RT, Schinski WL (2013) Chevron U.S.A. Inc., USA; Rutgers, The State University of New Jersey . US20130090503A1Google Scholar
  127. 127.
    McLain SJ, Wood CD, Schrock RR (1979) J Am Chem Soc 101:4558–4570CrossRefGoogle Scholar
  128. 128.
    Yang J, Qiao W, Li Z, Cheng L (2005) Fuel 84:1607–1611Google Scholar
  129. 129.
    Bhalla G, Bischof SM, Ganesh SK, Liu XY, Jones CJ, Borzenko A, Tenn WJ III, Ess DH, Hashiguchi BG, Lokare KS, Leung CH, Oxgaard J, Goddard IIIWA, Periana RA (2011) Green Chem 13:69–81CrossRefGoogle Scholar
  130. 130.
    Oxgaard J, Muller RP, Goddard WA, Periana RA (2003) J Am Chem Soc 126:352–363CrossRefGoogle Scholar
  131. 131.
    Foley NA, Lee JP, Ke Z, Gunnoe TB, Cundari TR (2009) Acc Chem Res 42:585–597CrossRefGoogle Scholar
  132. 132.
    He C, You F (2014) Ind Eng Chem Res 53:11442–11459CrossRefGoogle Scholar
  133. 133.
    Armor JN (2013) J Energy Chem 22:21–26CrossRefGoogle Scholar
  134. 134.
    Kundu S, Lyons TW, Brookhart M (2013) ACS Catal 3:1768–1773CrossRefGoogle Scholar
  135. 135.
    Lyons TW, Guironnet D, Findlater M, Brookhart M (2012) J Am Chem Soc 134:15708–15711CrossRefGoogle Scholar
  136. 136.
    Goldman AS, Dinh LV, Schinski WL (2013) Rutgers, The State University of New Jersey, USA; Chevron USA Inc. WO2013070316A1Google Scholar

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© Springer International Publishing Switzerland 2015

Authors and Affiliations

  1. 1.Department of ChemistryIndian Institute of Technology GuwahatiGuwahatiIndia
  2. 2.Department of Chemistry and Chemical BiologyRutgers-The State University of New JerseyPiscatawayUSA

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