Topics in Catalysis

, Volume 57, Issue 17–20, pp 1483–1489 | Cite as

Bifunctional Catalyst Control of Alkene Isomerization

  • Douglas B. GrotjahnEmail author
  • Casey R. Larsen
  • Gulin Erdogan


The ability to control the formation and chemistry of alkenes is of central importance to organic synthesis in both industry and academia. Progress in using catalysts with bifunctional (heteroaryl)phosphines to control positional and/or geometric selectivity in alkene isomerization and related chemistry is summarized.


Alkene Isomerization Bifunctional Phosphine Selectivity 



SDSU colleague Professor Andrew L. Cooksy is thanked for his invaluable role as co-author on many our papers on bifunctional catalysis and co-P.I. on Grants. Dr. LeRoy Lafferty has assisted the author and his students with NMR experiments. Professor Arnold Rheingold and his group have been invaluable for their X-ray diffraction expertise. The NSF is thanked for support of our research on bifunctional catalysis through Grants CHE-1059107, 0719575, and 0415783, and for an award upgrading the SDSU departmental NMR facility (MRI CHE-0521698).The San Diego Foundation is thanked for support by a Blasker award in 2006–2007.


  1. 1.
    Adams C (1999) Chem Ind 740Google Scholar
  2. 2.
    Helmchen G, Steinhagen H (1996) Angew Chem Int Ed 35:2339CrossRefGoogle Scholar
  3. 3.
    van den Beuken EK, Feringa BL (1998) Tetrahedron 54:12985CrossRefGoogle Scholar
  4. 4.
    Rowlands GJ (2001) Tetrahedron 57:1865CrossRefGoogle Scholar
  5. 5.
    Grotjahn DB (2005) Chem Eur J 11:7146CrossRefGoogle Scholar
  6. 6.
    Natale D, Mareque-Rivas JC (2008) Chem. Commun. (Cambridge) 4:425CrossRefGoogle Scholar
  7. 7.
    Rivas JCM (2007) Curr Org Chem 11:1434CrossRefGoogle Scholar
  8. 8.
    Jarvo ER, Copeland GT, Papaioannou N, Bonitatebus PJ Jr, Miller SJ (1999) J Am Chem Soc 121:11638CrossRefGoogle Scholar
  9. 9.
    Sigman MS, Vachal P, Jacobsen EN (2000) Angew Chem Int Ed 39:1279CrossRefGoogle Scholar
  10. 10.
    Dalko PI, Moisan L (2001) Angew Chem Int Ed Engl 40:3726CrossRefGoogle Scholar
  11. 11.
    Jarvo ER, Miller SJ (2002) Tetrahedron 58:2481CrossRefGoogle Scholar
  12. 12.
    Schreiner PR (2003) Chem Soc Rev 32:289CrossRefGoogle Scholar
  13. 13.
    Okino T, Hoashi Y, Takemoto Y (2003) J Am Chem Soc 125:12672CrossRefGoogle Scholar
  14. 14.
    Hamashima Y, Sawada D, Kanai M, Shibasaki M (1999) J Am Chem Soc 121:2641CrossRefGoogle Scholar
  15. 15.
    Funabashi K, Ratni H, Kanai M, Shibasaki M (2001) J Am Chem Soc 123:10784CrossRefGoogle Scholar
  16. 16.
    Shibasaki M, Kanai M, Matsunaga S, Kumagai N (2009) Acc Chem Res 42:1117CrossRefGoogle Scholar
  17. 17.
    Casas J, Najera C, Sansano JM, Saa JM (2002) Org Lett 4:2589CrossRefGoogle Scholar
  18. 18.
    France S, Wack H, Hafez AM, Taggi AE, Witsil DR, Lectka T (2002) Org Lett 4:1603CrossRefGoogle Scholar
  19. 19.
    Paull DH, Abraham CJ, Scerba MT, Alden-Danforth E, Lectka T (2008) Acc Chem Res 41:655CrossRefGoogle Scholar
  20. 20.
    Josephsohn NS, Kuntz KW, Snapper ML, Hoveyda AH (2001) J Am Chem Soc 123:11594CrossRefGoogle Scholar
  21. 21.
    DiMauro EF, Kozlowski MC (2002) J Am Chem Soc 124:12668CrossRefGoogle Scholar
  22. 22.
    Yi CS, Yun SY, He Z (2003) Organometallics 22:3031CrossRefGoogle Scholar
  23. 23.
    Noyori R, Yamakawa M, Hashiguchi S (2001) J Org Chem 66:7931CrossRefGoogle Scholar
  24. 24.
    Noyori R, Ohkuma T (2001) Angew Chem Int Ed Engl 40:40CrossRefGoogle Scholar
  25. 25.
    Ikariya T, Blacker AJ (2007) Acc Chem Res 40:1300CrossRefGoogle Scholar
  26. 26.
    Suzuki T, Morita K, Tsuchida M, Hiroi K (2002) Org Lett 4:2361CrossRefGoogle Scholar
  27. 27.
    Ito M, Osaku A, Kitahara S, Hirakawa M, Ikariya T (2003) Tet. Lett. 44:7521CrossRefGoogle Scholar
  28. 28.
    Casey CP, Singer SW, Powell DR, Hayashi RK, Kavana M (2001) J Am Chem Soc 123:1090CrossRefGoogle Scholar
  29. 29.
    Soo HS, Komor AC, Iavarone AT, Chang CJ (2009) Inorg Chem 48:10024CrossRefGoogle Scholar
  30. 30.
    Shook RL, Borovik AS (2008) Chem. Commun. (Cambridge) 46:6095CrossRefGoogle Scholar
  31. 31.
    Jensen DR, Schultz MJ, Mueller JA, Sigman MS (2003) Angew Chem Int Ed 42:3810CrossRefGoogle Scholar
  32. 32.
    Bagdanoff JT, Stoltz BM (2004) Angew. Chem. Int. Ed. 43:353–357CrossRefGoogle Scholar
  33. 33.
    Grotjahn DB, Combs D, Van S, Aguirre G, Ortega F (2000) Inorg Chem 39:2080CrossRefGoogle Scholar
  34. 34.
    Grotjahn DB, Van S, Combs D, Lev D, Schneider C, Rideout M, Meyer C, Hernandez G, Mejorado L (2002) J Org Chem 67:9200CrossRefGoogle Scholar
  35. 35.
    Grotjahn DB, Van S, Combs D, Lev DA, Incarvito C, Lam K-C, Rossi G, Rheingold AL, Rideout M, Meyer C, Hernandez G, Mejorado L (2003) Inorg Chem 42:3347CrossRefGoogle Scholar
  36. 36.
    Grotjahn DB (2008) Dalton Trans. 46:6497CrossRefGoogle Scholar
  37. 37.
    Grotjahn DB (2010) Pure Appl Chem 82:635CrossRefGoogle Scholar
  38. 38.
    Grotjahn DB (2010) Top Catal 53:1009CrossRefGoogle Scholar
  39. 39.
    Grotjahn DB (2010) Chem Lett 39:908CrossRefGoogle Scholar
  40. 40.
    Grotjahn DB, Lev DA (2004) J Am Chem Soc 126:12232CrossRefGoogle Scholar
  41. 41.
    Lev DA, Grotjahn DB (2005) Catal. Org. React. 104:237Google Scholar
  42. 42.
    Arita AJ, Cantada J, Grotjahn DB, Cooksy AL (2013) Organometallics 32:6867CrossRefGoogle Scholar
  43. 43.
    Grotjahn DB, Larsen CR, Gustafson JL, Nair R, Sharma A (2007) J Am Chem Soc 129:9592CrossRefGoogle Scholar
  44. 44.
    Erdogan G, Grotjahn DB (2009) J Am Chem Soc 131:10354CrossRefGoogle Scholar
  45. 45.
    Grotjahn DB, Larsen C, Erdogan G, Gustafson J, Sharma A, Nair R (2009) Catal. Org. React. 123:379Google Scholar
  46. 46.
    Larsen CR, Grotjahn DB (2012) J Am Chem Soc 134:10357CrossRefGoogle Scholar
  47. 47.
    Larsen CR, Grotjahn DB (2012) J Am Chem Soc 134:15604CrossRefGoogle Scholar
  48. 48.
    Plotkin JS (2005) Catal Today 106:10CrossRefGoogle Scholar
  49. 49.
    Otsuka S, Tani K (2004) In: Beller M, Bolm C (eds) Transition Metals for Organic Synthesis (2nd Edition), vol 1. Wiley-VCH, Weinheim, p 199CrossRefGoogle Scholar
  50. 50.
    Trost BM (2002) Acc Chem Res 35:695CrossRefGoogle Scholar
  51. 51.
    Kuznik N, Krompiec S (2007) Coord Chem Rev 251:222CrossRefGoogle Scholar
  52. 52.
    Krompiec S, Krompieca M, Penczeka R, Ignasiaka H (2008) Coord Chem Rev 252:1819CrossRefGoogle Scholar
  53. 53.
    Uma R, Crevisy C, Gree R (2003) Chem Rev 103:27CrossRefGoogle Scholar
  54. 54.
    Erdogan G, Grotjahn DB (2010) Top Catal 53:1055CrossRefGoogle Scholar
  55. 55.
    Prechtl MHG, Hoelscher M, Ben-David Y, Theyssen N, Loschen R, Milstein D, Leitner W (2007) Angew Chem Int Ed 46:2269CrossRefGoogle Scholar
  56. 56.
    Faller JW, Felkin H (1985) Organometallics 4:1488CrossRefGoogle Scholar
  57. 57.
    Faller JW, Smart CJ (1989) Organometallics 8:602CrossRefGoogle Scholar
  58. 58.
    Rybtchinski B, Cohen R, Ben-David Y, Martin JML, Milstein D (2003) J Am Chem Soc 125:11041CrossRefGoogle Scholar
  59. 59.
    Yung CM, Skaddan MB, Bergman RG (2004) J Am Chem Soc 126:13033CrossRefGoogle Scholar
  60. 60.
    Kohl G, Rudolph R, Pritzkow H, Enders M (2005) Organometallics 24:4774CrossRefGoogle Scholar
  61. 61.
    Zhou J, Hartwig JF (2008) Angew Chem Int Ed 47:5783CrossRefGoogle Scholar
  62. 62.
    Larsen CR, Erdogan G, Grotjahn DB (2014) J Am Chem Soc 136:1226CrossRefGoogle Scholar
  63. 63.
    McGowan KP, Abboud KA, Veige AS (2011) Organometallics 30:4949CrossRefGoogle Scholar
  64. 64.
    Sivaramakrishna A, Mushonga P, Rogers IL, Zheng F, Haines RJ, Nordlander E, Moss JR (2008) Polyhedron 27:1911CrossRefGoogle Scholar
  65. 65.
    Chianese AR, Shaner SE, Tendler JA, Pudalov DM, Shopov DY, Kim D, Rogers SL, Mo A (2012) Organometallics 31:7359CrossRefGoogle Scholar
  66. 66.
    Jennerjahn R, Jackstell R, Piras I, Franke R, Jiao H, Bauer M, Beller M (2012) ChemSusChem 5:734CrossRefGoogle Scholar
  67. 67.
    Mayer M, Welther A, von Wangelin AJ (2011) ChemCatChem 3:1567CrossRefGoogle Scholar
  68. 68.
    Kobayashi T, Yorimitsu H, Oshima K (2009) Chem Asian J 4:1078CrossRefGoogle Scholar
  69. 69.
    Morrill TC, D’Souza CA (2003) Organometallics 22:1626CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • Douglas B. Grotjahn
    • 1
    Email author
  • Casey R. Larsen
    • 1
  • Gulin Erdogan
    • 1
  1. 1.Department of Chemistry and BiochemistrySan Diego State UniversitySan DiegoUSA

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