Skip to main content
SpringerLink
Log in

Recent Advances in Alkane Dehydrogenation Catalyzed by Pincer Complexes

  • Chapter
  • First Online:
The Privileged Pincer-Metal Platform: Coordination Chemistry & Applications

Part of the book series: Topics in Organometallic Chemistry ((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.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Crabtree RH, Mihelcic JM, Quirk JM (1979) J Am Chem Soc 101:7738–7740

    Article  CAS  Google Scholar 

  2. Crabtree RH, Demou PC, Eden D, Mihelcic JM, Parnell CA, Quirk JM, Morris GE (1982) J Am Chem Soc 104:6994–7001

    Article  CAS  Google Scholar 

  3. Crabtree RH, Mellea MF, Mihelcic JM, Quirk JM (1982) J Am Chem Soc 104:107–113

    Article  CAS  Google Scholar 

  4. Baudry D, Ephritikhine M, Felkin H (1980) J Chem Soc Chem Commun 1243–1244

    Google Scholar 

  5. Baudry D, Ephritikhine M, Felkin H (1982) J Chem Soc Chem Commun 606–607

    Google Scholar 

  6. Baudry D, Ephritikhine M, Felkin H, Zakrzewski J (1982) J Chem Soc Chem Commun 1235–1236

    Google Scholar 

  7. Bergman RG (1984) Science 223:902–908

    Article  CAS  Google Scholar 

  8. Janowicz AH, Bergman RG (1982) J Am Chem Soc 104:352–354

    Article  CAS  Google Scholar 

  9. Janowicz AH, Bergman RG (1983) J Am Chem Soc 105:3929–3939

    Article  CAS  Google Scholar 

  10. Ghosh CK, Rodgers DPS, Graham WAG (1988) J Chem Soc Chem Commun 1511–12

    Google Scholar 

  11. Hoyano JK, Graham WAG (1982) J Am Chem Soc 104:3723–3725

    Article  CAS  Google Scholar 

  12. Rest AJ, Whitwell I, Graham WAG, Hoyano JK, McMaster AD (1984) J Chem Soc Chem Commun 624–626

    Google Scholar 

  13. Rest AJ, Whitwell I, Graham WAG, Hoyano JK, McMaster AD (1987) J Chem Soc Dalton Trans 1181

    Google Scholar 

  14. Harper TGP, Shinomoto RS, Deming MA, Flood TC (1988) J Am Chem Soc 110:7915–7916

    Article  CAS  Google Scholar 

  15. Jones WD, Feher FJ (1983) Organometallics 2:562–563

    Article  CAS  Google Scholar 

  16. Jones WD (2000) Science 287:1942–1943

    Google Scholar 

  17. Labinger JA, Bercaw JE (2002) Nature 417:507–514

    Article  CAS  Google Scholar 

  18. Goldberg KI, Goldman AS (eds) (2004) Activation and functionalization of C–H bonds. In: ACS symposium series 885, Washington, DC, American Chemical Society

    Google Scholar 

  19. Bergman RG (2007) Nature 446:506

    Article  CAS  Google Scholar 

  20. Crabtree RH (2010) Chem Rev 110:575

    Article  CAS  Google Scholar 

  21. Balcells D, Clot E, Eisenstein O (2010) Chem Rev 110:749–823

    Article  CAS  Google Scholar 

  22. Baudry D, Ephritikhine M, Felkin H, Holmes-Smith R (1983) J. Chem. Soc. Chem Commun 788–789

    Google Scholar 

  23. Goldman AS, Renkema KB, Czerw M, Krogh-Jespersen K (2004) Activation and Functionalization of C–H Bonds. ACS Symp Ser 885:198–215

    Article  CAS  Google Scholar 

  24. Burk MJ, Crabtree RH, Parnell CP, Uriarte RJ (1984) Organometallics 3:816–817

    Article  CAS  Google Scholar 

  25. Felkin H, Fillebeen-Khan T, Gault Y, Holmes-Smith R, Zakrzewski J (1984) Tetrahedron Lett 25:1279–1282

    Article  CAS  Google Scholar 

  26. Felkin H, Fillebeen-khan T, Holmes-Smith R, Yingrui L (1985) Tetrahedron Lett 26:1999–2000

    Article  CAS  Google Scholar 

  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. Burk MJ, Crabtree RH, McGrath DV (1985) J. Chem. Soc. Chem Commun 1829–1830

    Google Scholar 

  29. Burk MJ, Crabtree RH (1987) J Am Chem Soc 109:8025–8032

    Article  CAS  Google Scholar 

  30. Kunin AJ, Eisenberg R (1986) J Am Chem Soc 108:535–536

    Article  CAS  Google Scholar 

  31. Kunin AJ, Eisenberg R (1988) Organometallics 7:2124–2129

    Article  CAS  Google Scholar 

  32. Sakakura T, Sodeyama T, Tanaka M (1989) New J Chem 13:737–745

    CAS  Google Scholar 

  33. Sakakura T, Sodeyama T, Tokunaga Y, Tanaka M (1988) Chem Lett 17:263–264

    Article  Google Scholar 

  34. Sakakura T, Tanaka M (1987) Chem Let 16:249–252

    Article  Google Scholar 

  35. Sakakura T, Tanaka M (1987) J Chem Soc Chem Commun 758–759

    Google Scholar 

  36. Aoki T, Crabtree RH (1993) Organometallics 12:294–298

    Article  CAS  Google Scholar 

  37. Fujii T, Higashino Y, Saito Y (1993) J Chem Soc Dalton Trans 517–520

    Google Scholar 

  38. Fujii T, Saito Y (1990) J Chem Soc Chem Commun 757–758

    Google Scholar 

  39. Maguire JA, Boese WT, Goldman AS (1989) J Am Chem Soc 111:7088–7093

    Article  CAS  Google Scholar 

  40. Maguire JA, Goldman AS (1991) J Am Chem Soc 113:6706–6708

    Article  CAS  Google Scholar 

  41. Maguire JA, Petrillo A, Goldman AS (1992) J Am Chem Soc 114:9492–9498

    Article  CAS  Google Scholar 

  42. Chowdhury AD, Weding N, Julis J, Franke R, Jackstell R, Beller M (2014) Angew Chem Int Ed Engl 53:6477–6481

    Article  CAS  Google Scholar 

  43. Wang K, Goldman ME, Emge TJ, Goldman AS (1996) J Organomet Chem 518:55–68

    Article  CAS  Google Scholar 

  44. Gupta M, Hagen C, Flesher RJ, Kaska WC, Jensen CM (1996) Chem Commun 2083–2084

    Google Scholar 

  45. Gupta M, Hagen C, Kaska WC, Cramer RE, Jensen CM (1997) J Am Chem Soc 119:840–841

    Article  CAS  Google Scholar 

  46. Choi J, Goldman A (2011) Top Organometal Chem 34:139–167

    CAS  Google Scholar 

  47. Choi J, MacArthur AHR, Brookhart M, Goldman AS (2011) Chem Rev 111:1761–1779

    Article  CAS  Google Scholar 

  48. Findlater M, Choi J, Goldman AS, Brookhart M (2012) Catal Met Complexes 38:113–141

    Article  CAS  Google Scholar 

  49. Xu W-W, Rosini GP, Krogh-Jespersen K, Goldman AS, Gupta M, Jensen CM, Kaska WC (1997) Chem Commun 2273–2274

    Google Scholar 

  50. Liu F, Pak EB, Singh B, Jensen CM, Goldman AS (1999) J Am Chem Soc 121:4086–4087

    Article  CAS  Google Scholar 

  51. Liu FS, Goldman A (1999) Chem Commun 655–656

    Google Scholar 

  52. Haenel MW, Oevers S, Angermund K, Kaska WC, Fan H-J, Hall MB (2001) Angew Chem Int Ed Engl 40:3596–3600

    Article  CAS  Google Scholar 

  53. Punji B, Emge TJ, Goldman AS (2010) Organometallics 29:2702–2709

    Article  CAS  Google Scholar 

  54. Zhu K, Achord PD, Zhang X, Krogh-Jespersen K, Goldman AS (2004) J Am Chem Soc 126:13044–13053

    Article  CAS  Google Scholar 

  55. Huang Z, Brookhart M, Goldman AS, Kundu S, Ray A, Scott SL, Vicente BC (2009) Adv Synth Catal 351:188–206

    Article  CAS  Google Scholar 

  56. Kuklin SA, Sheloumov AM, Dolgushin FM, Ezernitskaya MG, Peregudov AS, Petrovskii PV, Koridze AA (2006) Organometallics 25:5466–5476

    Article  CAS  Google Scholar 

  57. Bezier D, Brookhart M (2014) ACS Catal 4:3411–3420

    Article  CAS  Google Scholar 

  58. Göttker-Schnetmann I, Brookhart M (2004) J Am Chem Soc 126:9330–9338

    Article  CAS  Google Scholar 

  59. Göttker-Schnetmann I, White P, Brookhart M (2004) J Am Chem Soc 126:1804–1811

    Article  CAS  Google Scholar 

  60. Göttker-Schnetmann I, White PS, Brookhart M (2004) Organometallics 23:1766–1776

    Article  CAS  Google Scholar 

  61. Ahuja R, Punji B, Findlater M, Supplee C, Schinski W, Brookhart M, Goldman AS (2011) Nature Chem 3:167–171

    Article  CAS  Google Scholar 

  62. Dobereiner GE, Yuan J, Schrock RR, Goldman AS, Hackenberg JD (2013) J Am Chem Soc 135:12572–12575

    Article  CAS  Google Scholar 

  63. Shi Y, Suguri T, Dohi C, Yamada H, Kojima S, Yamamoto Y (2013) Chem Eur J 19:10672–10689

    Article  CAS  Google Scholar 

  64. Yao W, Zhang Y, Jia X, Huang Z (2014) Angew Chem 126:1414–1418

    Article  Google Scholar 

  65. Jia X, Zhang L, Qin C, Leng X, Huang Z (2014) Chem Commun 50:11056–11059

    Article  CAS  Google Scholar 

  66. Morales-Morales D, Redón Ro, Yung C, Jensen CM (2004) Inorg Chim Acta 357:2953–2956

    Google Scholar 

  67. Kundu S, Choliy Y, Zhuo G, Ahuja R, Emge TJ, Warmuth R, Brookhart M, Krogh-Jespersen K, Goldman AS (2009) Organometallics 28:5432–5444

    Article  CAS  Google Scholar 

  68. Yao W, Zhang Y, Jia X, Huang Z (2014) Angew Chem Int Ed Engl 53:1390–1394

    Article  CAS  Google Scholar 

  69. Brayton DF, Beaumont PR, Fukushima EY, Sartain HT, Morales-Morales D, Jensen CM (2014) Organometallics 33:5198–5202

    Article  CAS  Google Scholar 

  70. Jia X, Zhang L, Qin C, Leng X, Huang Z (2014) Chem Commun 50:11056–11059

    Article  CAS  Google Scholar 

  71. Haibach MC, Kundu S, Brookhart M, Goldman AS (2012) Acc Chem Res 45:947–958

    Article  CAS  Google Scholar 

  72. Goldman AS, Roy AH, Huang Z, Ahuja R, Schinski W, Brookhart M (2006) Science 312:257–261

    Article  CAS  Google Scholar 

  73. Ahuja R, Kundu S, Goldman AS, Brookhart M, Vicente BC, Scott SL (2008) Chem Commun 253-255

    Google Scholar 

  74. Nawara-Hultzsch AJ, Hackenberg JD, Punji B, Supplee C, Emge TJ, Bailey BC, Schrock RR, Brookhart M, Goldman AS (2013) ACS Catal 3:2505–2514

    Article  CAS  Google Scholar 

  75. Goldman A, Ahuja R, Schinski W (2013) Rutgers, The State University of New Jersey, USA. US20130123552A1

    Google Scholar 

  76. Steffens AM, Goldman AS (2013) Abstracts of Papers, 245th ACS National Meeting & Exposition, New Orleans, LA, United States, April 7-11, 2013, INOR-1328

    Google Scholar 

  77. Leitch DC, Labinger JA, Bercaw JE (2014) Organometallics 33:3353–3365

    Article  CAS  Google Scholar 

  78. Leitch DC, Lam YC, Labinger JA, Bercaw JE (2013) J Am Chem Soc 135:10302–10305

    Article  CAS  Google Scholar 

  79. Gupta M, C. Kaska W, M. Jensen C (1997) Chem Commun 461–462

    Google Scholar 

  80. Jensen CM (1999) Chem. Commun 2443–2449

    Google Scholar 

  81. Zhang X, Fried A, Knapp S, Goldman AS (2003) Chem. Commun 2060–2061

    Google Scholar 

  82. Kumar A, Goldman AS (2013) Abstracts of Papers, 245th ACS National Meeting & Exposition, New Orleans, LA, United States, April 7-11, 2013, INOR-1202

    Google Scholar 

  83. Biswas S, Huang Z, Choliy Y, Wang DY, Brookhart M, Krogh-Jespersen K, Goldman AS (2012) J Am Chem Soc 134:13276–13295

    Article  CAS  Google Scholar 

  84. Knapp SMM, Shaner SE, Kim D, Shopov DY, Tendler JA, Pudalov DM, Chianese AR (2014) Organometallics 33:473–484

    Article  CAS  Google Scholar 

  85. Roddick DM (2013) Top Organomet Chem 40:49–88

    CAS  Google Scholar 

  86. Adams JJ, Arulsamy N, Roddick DM (2011) Organometallics 30:697–711

    Article  CAS  Google Scholar 

  87. Adams JJ, Arulsamy N, Roddick DM (2011) Dalton Trans 40:10014–10019

    Article  CAS  Google Scholar 

  88. Adams JJ, Arulsamy N, Roddick DM (2012) Organometallics 31:1439–1447

    Article  CAS  Google Scholar 

  89. Lee DW, Kaska WC, Jensen CM (1998) Organometallics 17:1–3

    Article  CAS  Google Scholar 

  90. Ghosh R, Kanzelberger M, Emge TJ, Hall GS, Goldman AS (2006) Organometallics 25:5668–5671

    Article  CAS  Google Scholar 

  91. Morales-Morales D, Lee DW, Wang Z, Jensen CM (2001) Organometallics 20:1144–1147

    Article  CAS  Google Scholar 

  92. Allen KE, Heinekey DM, Goldman AS, Goldberg KI (2014) Organometallics 33:1337–1340

    Article  CAS  Google Scholar 

  93. Allen KE, Heinekey DM, Goldman AS, Goldberg KI (2013) Organometallics 32:1579–1582

    Article  CAS  Google Scholar 

  94. Chianese AR, Drance MJ, Jensen KH, McCollom SP, Yusufova N, Shaner SE, Shopov DY, Tendler JA (2014) Organometallics 33:457–464

    Article  CAS  Google Scholar 

  95. Chianese AR, Mo A, Lampland NL, Swartz RL, Bremer PT (2010) Organometallics 29:3019–3026

    Article  CAS  Google Scholar 

  96. Chianese AR, Shaner SE, Tendler JA, Pudalov DM, Shopov DY, Kim D, Rogers SL, Mo A (2012) Organometallics 31:7359–7367

    Article  CAS  Google Scholar 

  97. Ito J-i, Kaneda T, Nishiyama H (2012) Organometallics 31:4442-4449

    Google Scholar 

  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-804

    Google Scholar 

  99. Kuznetsov VF, Abdur-Rashid K, Lough AJ, Gusev DG (2006) J Am Chem Soc 128:14388–14396

    Article  CAS  Google Scholar 

  100. Azerraf C, Gelman D (2009) Organometallics 28:6578–6584

    Article  CAS  Google Scholar 

  101. Gelman D, Romm R (2013) Organometal Pincer Chem 40:289–317

    CAS  Google Scholar 

  102. Musa S, Ackermann L, Gelman D (2013) Adv Synth Catal 355:3077–3080

    Article  CAS  Google Scholar 

  103. Huang Z, Rolfe E, Carson EC, Brookhart M, Goldman AS, El-Khalafy SH, MacArthur AHR (2010) Adv Synth Catal 352:125–135

    Article  CAS  Google Scholar 

  104. Gagliardo M, Chase PA, Brouwer S, van Klink GPM, van Koten G (2007) Organometallics 26:2219–2227

    Article  CAS  Google Scholar 

  105. Adams JJ, Gruver BC, Donohoue R, Arulsamy N, Roddick DM (2012) Dalton Trans 41:12601–12611

    Article  CAS  Google Scholar 

  106. Gruver BC, Adams JJ, Arulsamy N, Roddick DM (2013) Organometallics 32:6468–6475

    Article  CAS  Google Scholar 

  107. Gruver BC, Adams JJ, Warner SJ, Arulsamy N, Roddick DM (2011) Organometallics 30:5133–5140

    Article  CAS  Google Scholar 

  108. Kerr RA (2011) Science 331:1510–1511

    Article  CAS  Google Scholar 

  109. Murray J, King D (2012) Nature 481:433–435

    Article  CAS  Google Scholar 

  110. Brandt AR, Millard-Ball A, Ganser M, Gorelick SM (2013) Environ Sci Technol 47:8031–8041

    Article  CAS  Google Scholar 

  111. Huber GW, Iborra S, Corma A (2006) Chem Rev 106:4044–4098

    Article  CAS  Google Scholar 

  112. Graves C, Ebbesen SD, Mogensen M, Lackner KS (2011) Renew Sustain Energy Rev 15:1–23

    Article  CAS  Google Scholar 

  113. Dry ME (2002) J Chem Technol Biotechnol 77:43–50

    Article  CAS  Google Scholar 

  114. Dry ME (2002) Catalysis Today 71:227–241

    Article  CAS  Google Scholar 

  115. Dry ME (2004) Appl Catal A 276:1–3

    Article  CAS  Google Scholar 

  116. Leckel D (2009) Energy Fuels 23:2342–2358

    Article  CAS  Google Scholar 

  117. Hildebrandt D, Glasser D, Hausberger B, Patel B, Glasser BJ (2009) Science 323:1680–1681

    Article  Google Scholar 

  118. Burnett RL, Hughes TR (1973) J Catal 31:55–64

    Article  CAS  Google Scholar 

  119. Vidal V, Théolier A, Thivolle-Cazat J, Basset J-M (1997) Science 276:99–102

    Article  CAS  Google Scholar 

  120. Coperet C, Maury O, Thivolle-Cazat J, Basset J-M (2001) Angew Chem Int Ed Engl 40:2331–2334

    Article  CAS  Google Scholar 

  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 127:8604–8605

    Article  CAS  Google Scholar 

  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-670

    Google Scholar 

  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-681

    Google Scholar 

  124. Schrock RR (2001) Chem Rev 102:145–180

    Article  CAS  Google Scholar 

  125. Bailey BC, Schrock RR, Kundu S, Goldman AS, Huang Z, Brookhart M (2008) Organometallics 28:355–360

    Article  CAS  Google Scholar 

  126. Goldman AS, Stibrany RT, Schinski WL (2013) Chevron U.S.A. Inc., USA; Rutgers, The State University of New Jersey . US20130090503A1

    Google Scholar 

  127. McLain SJ, Wood CD, Schrock RR (1979) J Am Chem Soc 101:4558–4570

    Article  CAS  Google Scholar 

  128. Yang J, Qiao W, Li Z, Cheng L (2005) Fuel 84:1607–1611

    CAS  Google Scholar 

  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 13:69–81

    Article  CAS  Google Scholar 

  130. Oxgaard J, Muller RP, Goddard WA, Periana RA (2003) J Am Chem Soc 126:352–363

    Article  CAS  Google Scholar 

  131. Foley NA, Lee JP, Ke Z, Gunnoe TB, Cundari TR (2009) Acc Chem Res 42:585–597

    Article  CAS  Google Scholar 

  132. He C, You F (2014) Ind Eng Chem Res 53:11442–11459

    Article  CAS  Google Scholar 

  133. Armor JN (2013) J Energy Chem 22:21–26

    Article  CAS  Google Scholar 

  134. Kundu S, Lyons TW, Brookhart M (2013) ACS Catal 3:1768–1773

    Article  CAS  Google Scholar 

  135. Lyons TW, Guironnet D, Findlater M, Brookhart M (2012) J Am Chem Soc 134:15708–15711

    Article  CAS  Google Scholar 

  136. Goldman AS, Dinh LV, Schinski WL (2013) Rutgers, The State University of New Jersey, USA; Chevron USA Inc. WO2013070316A1

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati, 781039, Assam, India

    Akshai Kumar

  2. Department of Chemistry and Chemical Biology, Rutgers-The State University of New Jersey, 610 Taylor Road, Piscataway, NJ, 08854-8087, USA

    Alan S. Goldman

Authors
  1. Akshai Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Alan S. Goldman
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Akshai Kumar or Alan S. Goldman .

Editor information

Editors and Affiliations

  1. Organic Chemistry and Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, Utrecht, The Netherlands

    Gerard van Koten

  2. Department of Chemistry & Biology, Ryerson University, Toronto, Canada

    Robert A Gossage

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Kumar, A., Goldman, A.S. (2015). Recent Advances in Alkane Dehydrogenation Catalyzed by Pincer Complexes. In: van Koten, G., Gossage, R. (eds) The Privileged Pincer-Metal Platform: Coordination Chemistry & Applications. Topics in Organometallic Chemistry, vol 54. Springer, Cham. https://doi.org/10.1007/3418_2015_113

Download citation

Publish with us

Policies and ethics

Search

Navigation