Skip to main content
SpringerLink
Log in

New Concept of C–H and C–C Bond Activation via Surface Organometallic Chemistry

  • Chapter
  • First Online:
C-H Bond Activation and Catalytic Functionalization II

Part of the book series: Topics in Organometallic Chemistry ((volume 56))

Abstract

In this chapter we describe the recent applications of well-defined oxide-supported metal alkyls/alkylidenes/alkylidynes and hydrides of group IV, V, and VI transition metals in the field of C–H and C–C bond activation. The activation of ubiquitous C–H and C–C bonds of paraffin is a long-standing challenge because of intrinsic low reactivity. There are many concepts derived from surface organometallic chemistry (SOMC): surface organometallic fragments are always intermediates in heterogeneous catalysis. The study of their synthesis and reactivity is a way to rationalize mechanism of heterogeneous catalysis and to achieve structure activity relationship. By surface organometallic chemistry one can enter any catalytic center by a reaction intermediate leading in fine to single site catalysts. With surface organometallic chemistry one can coordinate to the metal which can play a role in different elementary steps leading for example to C–H activation and Olefin metathesis. Because of the development of SOMC there is a lot of space for the improvement of homogeneous catalysis. After the 1997 discovery of alkane metathesis using silica-supported tantalum hydride by Basset et al. at low temperature (150oC) the focus in this area was shifted to the discovery of more and more challenging surface complexes active in the application of C–H and C–C bond activation. Here we describe the evolution of well-defined metathesis catalyst with time as well as the effect of support on catalysis. We also describe here which metal–ligand combinations are responsible for a variety of C–H and C–C bond activation.

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. Vidal V, Theolier A, Thivolle-Cazat J, Basset JM (1997) Science 276:99–102

    Article  CAS  Google Scholar 

  2. Basset JM, Ugo R (2009) Modern surface organometallic chemistry. Wiley-VCH, Weinheim, pp 1–21

    Book  Google Scholar 

  3. Corker J, Lefebvre F, Lecuyer C, Dufaud V, Quignard F, Choplin A, Evans J, Basset JM (1996) Science 271:966–969

    Article  CAS  Google Scholar 

  4. Dufaud VR, Basset JM (1998) Angew Chem Int Ed 37:806–810

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  6. 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 

  7. Herisson JL, Chauvin Y (1971) Makromol Chem 141:161–176

    Article  CAS  Google Scholar 

  8. Schrock RR, Murdzek JS, Bazan GC, Robbins J, Dimare M, Oregan M (1990) J Am Chem Soc 112:3875–3886

    Article  CAS  Google Scholar 

  9. Bazan GC, Oskam JH, Cho HN, Park LY, Schrock RR (1991) J Am Chem Soc 113:6899–6907

    Article  CAS  Google Scholar 

  10. Schwab P, Grubbs RH, Ziller JW (1996) J Am Chem Soc 118:100–110

    Article  CAS  Google Scholar 

  11. Nguyen ST, Grubbs RH, Ziller JW (1993) J Am Chem Soc 115:9858–9859

    Article  CAS  Google Scholar 

  12. Ertl G (1983) J Vac Sci Technol A 1:1247–1253

    Article  CAS  Google Scholar 

  13. Cariati E, Dragonetti C, Lucenti E, Roberto D, Ugo R (2009) Modern surface organometallic chemistry. Wiley-VCH, Weinheim, pp 639–683

    Book  Google Scholar 

  14. Dragonetti C, Ceriotti A, Roberto D, Ugo R (2007) Organometallics 26:310–315

    Article  CAS  Google Scholar 

  15. Ballard DGH, Courtis A, Holton J, Mcmeeking J, Pearce R (1978) J Chem Soc Chem Commun 994–995

    Google Scholar 

  16. Popoff N, Mazoyer E, Pelletier J, Gauvin RM, Taoufik M (2013) Chem Soc Rev 42:9035–9054

    Article  CAS  Google Scholar 

  17. Nedez C, Theolier A, Lefebvre F, Choplin A, Basset JM, Joly JF (1993) J Am Chem Soc 115:722–729

    Article  CAS  Google Scholar 

  18. Wolke SI, Buffon R, Rodrigues UP (2001) J Organomet Chem 625:101–107

    Article  CAS  Google Scholar 

  19. Ajjou JAN, Scott SL, Paquet V (1998) J Am Chem Soc 120:415–416

    Article  CAS  Google Scholar 

  20. Bendjeriou-Sedjerari A, Azzi JM, Abou-Hamad E, Anjum DH, Pasha FA, Huang KW, Emsley L, Basset JM (2013) J Am Chem Soc 135:17943–17951

    Article  CAS  Google Scholar 

  21. Saint-Arroman RP, Chabanas M, Baudouin A, Copéret C, Basset JH, Lesage A, Emsley L (2001) J Am Chem Soc 123:3820–3821

    Article  CAS  Google Scholar 

  22. Le Roux E, Chabanas M, Baudouin A, de Mallmann A, Copéret C, Quadrelli EA, Thivolle-Cazat J, Basset JM, Lukens W, Lesage A, Emsley L, Sunley GJ (2004) J Am Chem Soc 126:13391–13399

    Article  Google Scholar 

  23. Samantaray MK, Callens E, Abou-Hamad E, Rossini AJ, Widdifield CM, Dey R, Emsley L, Basset JM (2014) J Am Chem Soc 136:1054–1061

    Article  CAS  Google Scholar 

  24. Chabanas M, Baudouin A, Copéret C, Basset JM (2001) J Am Chem Soc 123:2062–2063

    Article  CAS  Google Scholar 

  25. Berthoud R, Rendon N, Blanc F, Solans-Monfort X, Coperet C, Eisenstein O (2009) Dalton Trans 5879–5886

    Google Scholar 

  26. Quignard F, Lecuyer C, Choplin A, Olivier D, Basset JM (1992) J Mol Catal 74:353–363

    Article  CAS  Google Scholar 

  27. Niccolai GP, Basset JM (1998) Nato ASI 3 High Technol 44:111–124

    CAS  Google Scholar 

  28. Quignard F, Lecuyer C, Bougault C, Lefebvre F, Choplin A, Olivier D, Basset JM (1992) Inorg Chem 31:928–930

    Article  CAS  Google Scholar 

  29. Saint-Arroman RP, Basset JM, Lefebvre F, Didillon B (2005) Appl Catal A Gen 290:181–190

    Article  CAS  Google Scholar 

  30. Rosier C, Niccolai GP, Basset JM (1997) J Am Chem Soc 119:12408–12409

    Article  CAS  Google Scholar 

  31. Tosin G, Santini CC, Taoufik M, De Mallmann A, Basset JM (2006) Organometallics 25:3324–3335

    Article  CAS  Google Scholar 

  32. Larabi C, Merle N, Norsic S, Taoufik M, Baudouin A, Lucas C, Thivolle-Cazat J, de Mallmann A, Basset JM (2009) Organometallics 28:5647–5655

    Article  CAS  Google Scholar 

  33. Popoff N, Espinas J, Pelletier J, Macqueron B, Szeto KC, Boyron O, Boisson C, Del Rosal I, Maron L, De Mallmann A, Gauvin RM, Taoufik M (2013) Chem Eur J 19:964–973

    Article  CAS  Google Scholar 

  34. Rataboul F, Baudouin A, Thieuleux C, Veyre L, Copéret C, Thivolle-Cazat J, Basset JM, Lesage A, Emsley L (2004) J Am Chem Soc 126:12541–12550

    Article  CAS  Google Scholar 

  35. Tosin G, Santini CC, Baudouin A, De Mallman A, Fiddy S, Dablemont C, Basset JM (2007) Organometallics 26:4118–4127

    Article  CAS  Google Scholar 

  36. Chen Y, Abou-hamad E, Hamieh A, Hamzaoui B, Emsley L, Basset JM (2015) J Am Chem Soc 137:588–591

    Article  CAS  Google Scholar 

  37. Dufaud V, Niccolai GP, Thivolle-Cazat J, Basset JM (1995) J Am Chem Soc 117:4288–4294

    Article  CAS  Google Scholar 

  38. Lefort L, Chabanas M, Maury O, Meunier D, Copéret C, Thivolle-Cazat J, Basset JM (2000) J Organomet Chem 593:96–100

    Article  Google Scholar 

  39. Chabanas M, Quadrelli EA, Fenet B, Copéret C, Thivolle-Cazat J, Basset JM, Lesage A, Emsley L (2001) Angew Chem Int Ed 40:4493–4496

    Article  CAS  Google Scholar 

  40. Soignier S, Taoufik M, Le Roux E, Saggio G, Dablemont C, Baudouin A, Lefebvre F, de Mallmann A, Thivolle-Cazat J, Basset JM, Sunley G, Maunders BM (2006) Organometallics 25:1569–1577

    Article  CAS  Google Scholar 

  41. Saggio G, Mallmann A, Maunders B, Taoufik M, Thivolle-Cazat J, Basset J-M (2002) Organometallics 21:5167–5171

    Article  CAS  Google Scholar 

  42. Vidal V, Theolier A, Thivolle-Cazat J, Basset JM, Corker J (1996) J Am Chem Soc 118:4595–4602

    Article  CAS  Google Scholar 

  43. Delley MF, Nunez-Zarur F, Conley MP, Comas-Vives A, Siddiqi G, Norsic S, Monteil V, Safonova OV, Copéret C (2014) Proc Natl Acad Sci U S A 111:11624–11629

    Article  CAS  Google Scholar 

  44. Le Roux E, Taoufik M, Chabanas M, Alcor D, Baudouin A, Copéret C, Thivolle-Cazat J, Basset JM, Lesage A, Hediger S, Emsley L (2005) Organometallics 24:4274–4279

    Article  Google Scholar 

  45. Le Roux E, Taoufik M, Copéret C, de Mallmann A, Thivolle-Cazat J, Basset JM, Maunders BM, Sunley GJ (2005) Angew Chem Int Ed 44:6755–6758

    Article  Google Scholar 

  46. Szeto KC, Norsic S, Hardou L, Le Roux E, Chakka S, Thivolle-Cazat J, Baudouin A, Papaioannou C, Basset JM, Taoufik M (2010) Chem Commun 46:3985–3987

    Article  CAS  Google Scholar 

  47. Galyer L, Mertis K, Wilkinson G (1975) J Organomet Chem 85:C37–C38

    Article  CAS  Google Scholar 

  48. Marks TJ (1992) Acc Chem Res 25:57–65

    Article  CAS  Google Scholar 

  49. Samantaray MK, Dey R, Abou-Hamad E, Hamieh A, Basset JM (2015) Chem Eur J 21:6100–6106

    Article  CAS  Google Scholar 

  50. Green MLH (1995) J Organomet Chem 500:127–148

    Article  CAS  Google Scholar 

  51. Basset JM, Copéret C, Soulivong D, Taoufik M, Thivolle-Cazat J (2006) Angew Chem Int Ed 45:6082–6085

    Article  CAS  Google Scholar 

  52. Leconte M, Basset JM (1979) J Am Chem Soc 101:7296–7302

    Article  CAS  Google Scholar 

  53. Basset JM, Copéret C, Soulivong D, Taoufik M, Cazat JT (2010) Acc Chem Res 43:323–334

    Article  CAS  Google Scholar 

  54. Vidal V, Theolier A, Thivolle-Cazat J, Basset JM (1995) J Chem Soc Chem Commun 991–992

    Google Scholar 

  55. Copéret C, Maury O, Thivolle-Cazat J, Basset JM (2001) Angew Chem Int Ed 40:2331–2334

    Article  Google Scholar 

  56. 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 

  57. Avenier P, Taoufik M, Lesage A, Solans-Monfort X, Baudouin A, de Mallmann A, Veyre L, Basset JM, Eisenstein O, Emsley L, Quadrelli EA (2007) Science 317:1056–1060

    Article  CAS  Google Scholar 

  58. Pasha FA, Cavallo L, Basset JM (2014) ACS Catal 4:1868–1874

    Article  CAS  Google Scholar 

  59. Vanasselt A, Santarsiero BD, Bercaw JE (1986) J Am Chem Soc 108:8291–8293

    Article  CAS  Google Scholar 

  60. Parkin G, Bunel E, Burger BJ, Trimmer MS, Vanasselt A, Bercaw JE (1987) J Mol Catal 41:21–39

    Article  CAS  Google Scholar 

  61. Sharp PR, Astruc D, Schrock RR (1979) J Organomet Chem 182:477–488

    Article  CAS  Google Scholar 

  62. Wallace KC, Dewan JC, Schrock RR (1986) Organometallics 5:2162–2164

    Article  CAS  Google Scholar 

  63. Wallace KC, Liu AH, Dewan JC, Schrock RR (1988) J Am Chem Soc 110:4964–4977

    Article  CAS  Google Scholar 

  64. Turner HW, Schrock RR (1982) J Am Chem Soc 104:2331–2333

    Article  CAS  Google Scholar 

  65. Mclain SJ, Sancho J, Schrock RR (1979) J Am Chem Soc 101:5451–5453

    Article  CAS  Google Scholar 

  66. Schinzel S, Chermette H, Copéret C, Basset JM (2008) J Am Chem Soc 130:7984–7987

    Article  CAS  Google Scholar 

  67. Chabanas M, Vidal V, Copéret C, Thivolle-Cazat J, Basset JM (2000) Angew Chem Int Ed 39:1962–1965

    Article  CAS  Google Scholar 

  68. Watson PL (1983) J Am Chem Soc 105:6491–6493

    Article  CAS  Google Scholar 

  69. Chen Y, Ould-Chikh S, Abou-Hamad E, Callens E, Mohandas JC, Khalid S, Basset JM (2014) Organometallics 33:1205–1211

    Article  CAS  Google Scholar 

  70. Le Roux E, Taoufik M, Baudouin A, Copéret C, Thivolle-Cazat J, Basset JM, Maunders BM, Sunley GJ (2007) Adv Synth Catal 349:231–237

    Article  Google Scholar 

  71. Taoufik M, Le Roux E, Thivolle-Cazat J, Copéret C, Basset JM, Maunders B, Sunley GJ (2006) Top Catal 40:65–70

    Article  CAS  Google Scholar 

  72. Callens E, Abou-Hamad E, Riache N, Basset JM (2014) Chem Commun 50:3982–3985

    Article  CAS  Google Scholar 

  73. Buffon R, Leconte M, Choplin A, Basset JM (1994) J Chem Soc Dalton 1723–1729

    Google Scholar 

  74. Riache N, Callens E, Espinas J, Dery A, Samantaray MK, Dey R, Basset JM (2015) Catal Sci Technol 5:280–285

    Article  CAS  Google Scholar 

  75. 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 

  76. Rascon F, Coperet C (2011) J Organomet Chem 696:4121–4131

    Article  CAS  Google Scholar 

  77. Domski GJ, Rose JM, Coates GW, Bolig AD, Brookhart M (2007) Prog Polym Sci 32:30–92

    Article  CAS  Google Scholar 

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

    Google Scholar 

  79. Riache N, Callens E, Samantaray MK, Kharbatia NM, Atiqullah M, Basset JM (2014) Chem Eur J 20:15089–15094

    Article  CAS  Google Scholar 

  80. Merle N, Stoffelbach F, Taoufik M, Le Roux E, Thivolle-Cazat J, Basset JM (2009) Chem Commun 2523–2525

    Google Scholar 

  81. Taoufik M, Schwab E, Schultz M, Vanoppen D, Walter M, Thivolle-Cazat J, Basset JM (2004) Chem Commun 1434–1435

    Google Scholar 

  82. Soulivong D, Copéret C, Thivolle-Cazat J, Basset JM, Maunders BM, Pardy RBA, Sunley GJ (2004) Angew Chem Int Ed 43:5366–5369

    Article  CAS  Google Scholar 

  83. Polshettiwar V, Thivolle-Cazat J, Taoufik M, Stoffelbach F, Norsic S, Basset JM (2011) Angew Chem Int Ed 50:2747–2751

    Article  CAS  Google Scholar 

  84. Watson PL, Parshall GW (1985) Acc Chem Res 18:51–56

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology, 23955-6900, Thuwal, Saudi Arabia

    Manoja K. Samantaray, Raju Dey, Santosh Kavitake & Jean-Marie Basset

Authors
  1. Manoja K. Samantaray
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Raju Dey
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Santosh Kavitake
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jean-Marie Basset
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jean-Marie Basset .

Editor information

Editors and Affiliations

  1. Université de Rennes, Rennes, France

    Pierre H. Dixneuf

  2. Université de Rennes, Rennes, France

    Henri Doucet

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Samantaray, M.K., Dey, R., Kavitake, S., Basset, JM. (2015). New Concept of C–H and C–C Bond Activation via Surface Organometallic Chemistry. In: Dixneuf, P., Doucet, H. (eds) C-H Bond Activation and Catalytic Functionalization II. Topics in Organometallic Chemistry, vol 56. Springer, Cham. https://doi.org/10.1007/3418_2015_139

Download citation

Publish with us

Policies and ethics

Search

Navigation