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Rhodium Catalyzed Decarbonylation

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Rhodium Catalysis

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 61))

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Abstract

Rhodium catalyzed decarbonylation has developed significantly over the last 50 years and resulted in a wide range of reported catalyst systems and reaction protocols. Besides experimental data, literature also includes mechanistic studies incorporating Hammett methods, analysis of kinetic isotope effects as well as computational studies of model systems, which give an indication of the scope of the process. In this chapter, fundamental applications of Rh-catalyzed decarbonylation reactions are surveyed and discussed, including cross-coupling reactions, tandem reactions, and alternative methodologies for process intensification.

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References

  1. Bierhals J (2012) Carbon monoxide. In: Ullmann’s encyclopedia of industrial chemistry. Wiley-VCH, Weinheim

    Google Scholar 

  2. Elschenbroich C, Salzer A (2006) Organometallics: a concise introduction. Wiley-VCH, Weinheim

    Google Scholar 

  3. Omaye ST (2002) Toxicology 180:139

    Article  CAS  Google Scholar 

  4. Necas D, Kotora M (2007) Curr Org Chem 11:1566

    Article  CAS  Google Scholar 

  5. Tsuji J, Ohno K (1965) Tetrahedron Lett 44:3969

    Google Scholar 

  6. Doughty DH, Pignolet LH (1978) J Am Chem Soc 100:7083

    Article  CAS  Google Scholar 

  7. Beck CM, Rathmill SE, Park YJ, Chen J, Crabtree RH, Liable-Sands LM, Rheingold AL (1999) Organometallics 18:5311

    Article  CAS  Google Scholar 

  8. Fristrup P, Kreis M, Palmelund A, Norrby P-O, Madsen R (2008) J Am Chem Soc 130:5206

    Article  CAS  Google Scholar 

  9. Gutmann B, Elsner P, Glasnov T, Roberge DM, Kappe CO (2014) Angew Chem Int Ed 53:11557

    Article  CAS  Google Scholar 

  10. Moritani I, Fujiwara Y (1968) Tetrahedron Lett 24:4819

    Article  Google Scholar 

  11. Ueura K, Satoh T, Miura M (2007) Org Lett 9:1407

    Article  CAS  Google Scholar 

  12. Baudoin O (2007) Angew Chem Int Ed 46:1373

    Article  CAS  Google Scholar 

  13. Goossen LJ, Rodriguez N, Goossen K (2008) Angew Chem Int Ed 47:3100

    Article  CAS  Google Scholar 

  14. Qiu R, Zhang L, Xu C, Pan Y, Pang H, Xu L, Li H (2015) Adv Synth Catal 357:1229

    Article  CAS  Google Scholar 

  15. Jin W, Yu Z, He W, Ye W, Xiao W-J (2009) Org Lett 11:1317

    Article  CAS  Google Scholar 

  16. Zhao XD, Yu ZJ (2008) J Am Chem Soc 130:8136

    Article  CAS  Google Scholar 

  17. Ye W, Luo N, Yu Z (2010) Organometallics 29:1049

    Article  CAS  Google Scholar 

  18. Heck FR, Nolley JP (1972) J Org Chem 37:2320

    Article  CAS  Google Scholar 

  19. Mizoroki T, Mori K, Ozaki A (1971) Bull Chem Soc Jpn 44:581

    Article  CAS  Google Scholar 

  20. Kang L, Zhang F, Ding L-T, Yang L (2015) RSC Adv 5:100452

    Article  CAS  Google Scholar 

  21. Yang F-L, Ma X-T, Trian S-K (2012) Chem Eur J 18:1582

    Article  CAS  Google Scholar 

  22. Zhang Y-G, Liu X-L, He Z-Y, Li X-M, Kang H-J, Tian S-K (2014) Chem Eur J 20:2765

    Article  CAS  Google Scholar 

  23. Yang L, Correia CA, Guo X, Li CJ (2010) Tetrahedron Lett 51:5486

    Article  CAS  Google Scholar 

  24. Sugihara T, Satoh T, Miura M, Nomura M (2003) Angew Chem Int Ed 42:4672

    Article  CAS  Google Scholar 

  25. Sugihara T, Satoh T, Miura M, Nomura M (2004) Adv Synth Catal 346:1765

    Article  CAS  Google Scholar 

  26. Yang L, Zeng T, Shuai Q, Guo X, Li C-J (2011) Chem Commun 47:2161

    Article  CAS  Google Scholar 

  27. Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M (2002) Chem Rev 102:1359

    Article  CAS  Google Scholar 

  28. Ashenhurst JA (2010) Chem Soc Rev 39:540

    Article  CAS  Google Scholar 

  29. Li C-J (2009) Acc Chem Res 42:335

    Article  CAS  Google Scholar 

  30. Baslé O, Bidange J, Shuai Q, Li C-J (2010) Adv Synth Catal 352:1145

    Article  Google Scholar 

  31. Guo X, Wang J, Li C-J (2009) J Am Chem Soc 131:15092

    Article  CAS  Google Scholar 

  32. Guo X, Wang J, Li C-J (2010) Org Lett 12:3176

    Article  CAS  Google Scholar 

  33. Shaui Q, Yang L, Guo X, Basle O, Li C-J (2010) J Am Chem Soc 132:12212

    Article  Google Scholar 

  34. Yang L, Guo X, Li C-J (2010) Adv Synth Catal 352:2899

    Article  CAS  Google Scholar 

  35. Guo X, Wang J, Li C-J (2009) J Am Chem Soc 131:15092

    Article  CAS  Google Scholar 

  36. Tietze LF, Beifuss U (1993) Angew Chem Int Ed 32:131

    Article  Google Scholar 

  37. Pellissier H (2006) Tetrahedron 26:1619

    Article  Google Scholar 

  38. Nicolaou KC, Edmonds DJ, Bulger PG (2006) Angew Chem Int Ed 45:7134

    Article  CAS  Google Scholar 

  39. Pellissier H (2006) Tetrahedron 62:2143

    Article  CAS  Google Scholar 

  40. Enders D, Grondal C, Hüttl MRM (2007) Angew Chem Int Ed 46:1570

    Article  CAS  Google Scholar 

  41. Grondal C, Jeanty M, Enders D (2010) Nat Chem 2:167

    Article  CAS  Google Scholar 

  42. Kreis M, Palmelund A, Bunch L, Madsen R (2006) Adv Synth Catal 348:2148–2154

    Article  CAS  Google Scholar 

  43. Dierkes P, van Leeuwen PWNM (1999) J Chem Soc Dalton Trans 1519

    Google Scholar 

  44. Old DW, Wolfe JP, Buchwald SL (1998) J Am Chem Soc 120:9722

    Article  CAS  Google Scholar 

  45. Poulsen CS, Madsen RJ (2002) Org Chem 67:4441

    Article  CAS  Google Scholar 

  46. Burke MD, Schreiber SL (2004) Angew Chem Int Ed 43:46

    Article  Google Scholar 

  47. Fessard TC, Andrews SP, Motoyoshi H, Carreira EM (2007) Angew Chem Int Ed 46:9331

    Article  CAS  Google Scholar 

  48. Bell S, Wuestenberg B, Kaiser S, Menges F, Pfaltz A (2006) Science 311:5761

    Article  Google Scholar 

  49. Fessard TC, Motoyoshi H, Carreira EM (2007) Angew Chem Int Ed 46:2078

    Article  CAS  Google Scholar 

  50. Paquin JF, Defieber C, Stephenson CRJ, Carreira EM (2005) J Am Chem Soc 127:10850

    Article  CAS  Google Scholar 

  51. Morimoto T, Fuji K, Tsutsumi K, Kakiuchi K (2002) J Am Chem Soc 124:3806

    Article  CAS  Google Scholar 

  52. Morimoto T, Fujioka M, Fuji K, Tsutsumi K, Kakiuchi K (2007) J Organomet Chem 692:625

    Article  CAS  Google Scholar 

  53. Gedye R, Smith F, Westaway K, Ali H, Baldisera L, Laberge L, Rousell J (1986) Tetrahedron Lett 27:279

    Article  CAS  Google Scholar 

  54. Giguere RJ, Bray TL, Duncan SM, Majetich G (1986) Tetrahedron Lett 27:4945

    Article  CAS  Google Scholar 

  55. Kappe CO (2004) Angew Chem Int Ed 43:6250

    Article  CAS  Google Scholar 

  56. Kappe CO, Dallinger D (2006) Nat Rev Drug Discov 5:51

    Article  CAS  Google Scholar 

  57. Lee H-W, Lee L-N, Chan ASC, Kwong F-Y (2008) Eur J Org Chem 19:3403

    Google Scholar 

  58. Monard RN, Madsen R (2007) J Org Chem 7:9782

    Article  Google Scholar 

  59. Györgydeák Z, Pelyvás IF (1998) Monosaccharide sugars: chemical synthesis by chain elongation, degradation and epimerization. Academic Press, San Diego

    Google Scholar 

  60. Ruff O (1898) Chem Ber 31:1573

    Article  CAS  Google Scholar 

  61. Hendriks HEJ, Kuster BFM, Marin GB (1991) Carbohydr Res 214:71

    Article  CAS  Google Scholar 

  62. Humphlett WJ (1967) Carbohydr Res 4:157

    Article  CAS  Google Scholar 

  63. Monrad RN, Madsen R (2007) J Org Chem 72:9782

    Article  Google Scholar 

  64. Andrews MA, Gould GL, Klaeren SA (1989) J Org Chem 54:5257

    Article  CAS  Google Scholar 

  65. Cole-Hamilton DJ, Tooze RP (2006) Homogeneous catalysis – advantages and problems. In: Cole-Hamilton DJ, Tooze RP (eds) Catalyst separation, recovery and recycling, Catalysis by metal complexes, vol 30. Springer, Dordrecht

    Chapter  Google Scholar 

  66. Haumann M, Riisager A (2008) Chem Rev 108:1474

    Article  CAS  Google Scholar 

  67. Garcia-Suarez EJ, Khokarale SG, Van Buu ON, Fehrmann R, Riisager A (2014) Green Chem 16:161

    Article  CAS  Google Scholar 

  68. Malcho P, Garcia-Suarez EJ, Riisager A (2014) RSC Adv 4:58151

    Article  CAS  Google Scholar 

  69. Bröhmer MC, Volz N, Bräse S (2009) Synlett 1383–1386

    Google Scholar 

  70. Malcho P, Garcia-Suarez EJ, Mentzel UV, Engelbrekt C, Riisager A (2014) Dalton Trans 43:17230

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Centre for Catalysis and Sustainable Chemistry, Department of Chemistry, Technical University of Denmark, Building 207, 2800 Kgs., Lyngby, Denmark

    Eduardo J. García-Suárez, Klara Kahr & Anders Riisager

Authors
  1. Eduardo J. García-Suárez
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  2. Klara Kahr
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  3. Anders Riisager
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Corresponding authors

Correspondence to Eduardo J. García-Suárez or Anders Riisager .

Editor information

Editors and Affiliations

  1. Facultat de Química, Universitat Rovira i Virgili, Tarragona, Spain

    Carmen Claver

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García-Suárez, E.J., Kahr, K., Riisager, A. (2017). Rhodium Catalyzed Decarbonylation. In: Claver, C. (eds) Rhodium Catalysis. Topics in Organometallic Chemistry, vol 61. Springer, Cham. https://doi.org/10.1007/3418_2017_175

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