Skip to main content
SpringerLink
Log in

Domino Reactions Triggered by Hydroformylation

  • Chapter
  • First Online:
Hydroformylation for Organic Synthesis

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 342))

Abstract

HF reaction represents a selective method for the synthesis of aldehydes starting from alkenes. Because of versatile aldehydes reactivity, it is possible to perform different domino protocols based on contemporary HF, including Michael’s reaction, reductive amination, cyclopropanation, lactonization, and many others. This overview reports on the last 5 years’ results obtained on this field.

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 229.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 299.99
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

Abbreviations

6-DPPon:

6-(Diphenylphosphino)pyridin-2(1H)-one

Bcope:

Bis(cyclooctyl)phosphine ethane

BISBI:

2,2′-Bis(diphenylphosphinomethyl)-1,1′-biphenyl

CTAB:

Cetyltrimethylammonium bromide

DPPB:

1,4-Bis(diphenylphosphino)butane

HAM:

Hydroaminomethylation

HF:

Hydroformylation

HFIPA:

Hexafluoroisopropanol

MW:

Microwave

NAPHOS:

2,2'-Bis[(diphenylphosphino)methyl]-1,1'-binaphthyl

NaTPPTS:

Sodium triphenylphosphinetrisulfonate

TETRABI:

2,2′,6,6′-Tetrakis((diphenylphosphino)-methyl)-1,1′-biphenyl

References

  1. Franke R, Selent D, Börner A (2012) Chem Rev 112:5675–5732

    Google Scholar 

  2. Tietze LF, Beifuss U (1993) Angew Chem Int Ed Engl 32:131–163

    Article  Google Scholar 

  3. Tietze L (1996) Chem Rev 96:115–136

    Article  CAS  Google Scholar 

  4. Pellissier H (2011) Chem Rev 113:442–524

    Article  Google Scholar 

  5. Eilbracht P, Barfacker L, Buss C, Hollmann C, Kitsos-Rzychon BE, Kranemann CL, Rische T, Roggenbuck R, Schmidt A (1999) Chem Rev 99:3329–3365

    Article  CAS  Google Scholar 

  6. Reppe W (1943) (IG Farben). DRP. a. I. 74,946

    Google Scholar 

  7. Reppe W (1949) Experientia 5:93

    Article  CAS  Google Scholar 

  8. Olin JF, Deger TE (1947) Sharpless Chemicals Inc., U.S. Patent 2,422,631. Chem Abstr 41:5892a

    Google Scholar 

  9. Ahmed M, Seayad AM, Jackstell R, Beller M (2003) J Am Chem Soc 125:10311–10318

    Article  CAS  Google Scholar 

  10. Liu G, Huang K, Cai C, Cao B, Chang M, Wu W, Zhang X (2011) Chem Eur J 17:14559–14563

    Article  CAS  Google Scholar 

  11. Fuentes JA, Wawrzyniak P, Roff GJ, Bühl M, Clarke ML (2011) Catal Sci Technol 1:431–436

    Article  CAS  Google Scholar 

  12. Oliveira KCB, Santos AG, dos Santos EN (2012) App Catal A General 445–446:204–208

    Article  Google Scholar 

  13. Wang YY, Lou MM, Li YZ, Chen H, Li XJ (2004) App Catal A Gen 272:151–155

    Article  CAS  Google Scholar 

  14. Wang Y, Chen J, Lou M, Chen H, Li X (2006) Catal Commun 7:979–981

    Article  CAS  Google Scholar 

  15. Behr A, Becker M, Reyer S (2010) Tetrahedron Lett 51:2438–2441

    Article  CAS  Google Scholar 

  16. Vasyluev M, Alper H (2010) Synthesis 2893–2900

    Google Scholar 

  17. Lin YS, El Ali B, Alper H (2001) J Am Chem Soc 123:7719–7720

    Article  CAS  Google Scholar 

  18. Crozet D, Gual A, McKay D, Dinoi C, Godard C, Urrutigoïty M, Daran J-C, Maron L, Claver C, Kalck P (2012) Chem Eur J 18:7128–7140

    Article  CAS  Google Scholar 

  19. Gall B, Bortenschlager M, Nuyken O, Weberskirch R (2008) Macromol Chem Phys 4:1152–1159

    Google Scholar 

  20. Makado G, Morimoto T, Sugimoto Y, Tsutsumi K, Kagawa N, Kakiuchi K (2010) Adv Synth Catal 352:299–304

    Article  CAS  Google Scholar 

  21. Srivastava VK, Eilbracht P (2009) Catal Commun 10:1791–1795

    Article  CAS  Google Scholar 

  22. Briggs JR, Klosin J, Whiteker GT (2005) Org Lett 7:4795–4798

    Article  CAS  Google Scholar 

  23. Seayad A, Ahmed M, Klein H, Jackstell R, Gross T, Beller M (2002) Science 297:1676–1678

    Article  CAS  Google Scholar 

  24. Ahmed M, Bronger RPJ, Jackstell R, Kamer PCJ, van Leeuwen PWNM, Beller M (2006) Chem Eur J 12:8979–8988

    Google Scholar 

  25. Liu G, Huang K, Cao B, Chang M, Li S, Yu S, Zhou L, Wu W, Zhang X (2012) Org Lett 14:102–105

    Article  CAS  Google Scholar 

  26. Spangenberg T, Breit B, Mann A (2009) Org Lett 11:261–264

    Article  CAS  Google Scholar 

  27. Sacher JR, Weinreb SM (2012) Org Lett 14:2172–2175

    Article  CAS  Google Scholar 

  28. Kazumi O, Alper H (2010) Tetrahedron Lett 51:4959–4961

    Article  Google Scholar 

  29. Vasylyev M, Alper H (2010) Synthesis 2893–2900

    Google Scholar 

  30. Vieira TO, Alper H (2007) Chem Commun 2710–2711

    Google Scholar 

  31. Cobley CJ, Hanson CH, Lloyd MC, Simmonds S (2011) Org Proc Res Dev 15:284–290

    Article  CAS  Google Scholar 

  32. Ojima I, Tzamarioudaki M, Eguchi M (1995) J Org Chem 60:7078–7079

    Article  CAS  Google Scholar 

  33. Ojima I, Tzamarioudaki M, Eguchi M (1998) Tetrahedron Lett 39:4599–4602

    Article  CAS  Google Scholar 

  34. Chiou W-H, Lee S-Y, Ojima I (2005) Can J Chem 83:681–692

    Article  CAS  Google Scholar 

  35. Chiou W-H, Mizutani N, Ojima I (2007) J Org Chem 72:1871–1882

    Article  CAS  Google Scholar 

  36. Bates RW, Sivarajan K, Straub BF (2011) J Org Chem 76:6844–6848

    Article  CAS  Google Scholar 

  37. Chiou W-H, Lin G-H, Liang C-W (2010) J Org Chem 75:1748–1751

    Article  CAS  Google Scholar 

  38. Chiou W-H, Schoenfelder A, Sun L, Mann A, Ojima I (2007) J Org Chem 72:9418–9425

    Article  CAS  Google Scholar 

  39. Airiau E, Spangenberg T, Girard N, Schoenfelder A, Salvadori J, Taddei M, Mann A (2008) Chem Eur J 14:10938–10948

    Article  CAS  Google Scholar 

  40. Zill N, Schoenfelder A, Girard N, Taddei M, Mann A (2012) J Org Chem 77:2246–2253

    Article  CAS  Google Scholar 

  41. Chiou W-H, Lin G-H, Hsu C-C, Chaterpaul SJ, Ojima I (2009) Org Lett 11:2659–2662

    Article  CAS  Google Scholar 

  42. Lazzaroni R, Settambolo R (2011) Chirality 23:730–735

    Article  CAS  Google Scholar 

  43. Chiou W-H, Lin Y-H, Chen G-T, Gao Y-K, Kao C-L, Tsai J-C (2011) Chem Commun 47:3562–3564

    Google Scholar 

  44. Crause C, Bennie L, Damoense L, Dwyer CL, Grove C, Grimmer N, Rensburg WJV, Kirk MM, Mokheseng KM, Otto S, Steynberg PJ (2003) Dalton Trans 2036

    Google Scholar 

  45. Moreno MA, Haukka M, Turunen A, Pakkanen TA (2005) J Mol Catal A 240:7–15

    Article  CAS  Google Scholar 

  46. Konya D, Almeida Lenero KQ, Drent E (2006) Organometallics 25:3166

    Google Scholar 

  47. Diab L, Smejkal T, Geier J, Breit B (2009) Angew Chem Int Ed 48:8022–8026

    Article  CAS  Google Scholar 

  48. Boogaerts IIF, White DFS, Cole-Hamilton DJ (2010) Chem Commun 46:2194

    Google Scholar 

  49. Takahashi K, Yamashita M, Ichihara T, Nakano K, Nozaki K (2010) Angew Chem Int Ed 49:4488–4490

    Article  CAS  Google Scholar 

  50. Panda AG, Jagtap SR, Nandurlar NS, Bhanage BM (2008) Ind Eng Chem Res 47:969–972

    Article  CAS  Google Scholar 

  51. Fleischer I, Dyballa KM, Jennerjahn R, Jackstell R, Franke R, Spannenberg A, Beller M (2013) Angew Chem Int Ed 52:1–6

    Article  Google Scholar 

  52. Konya D, Leñero KQA, Drent E (2006) Organometallics 25:3166–3174

    Article  CAS  Google Scholar 

  53. Mondon M, Fontelle N, Desire J, Lecornue F, Guillard J, Marrot J, Bleriot Y (2012) Org Lett 14:870–873

    Article  CAS  Google Scholar 

  54. Muncipinto G, Moquist PN, Schreiber SL, Schaus SE (2011) Angew Chem Int Ed 50:8172–8175

    Article  CAS  Google Scholar 

  55. Dirat O, Bibb AJ, Burns CM, Checksfield GD, Dillon BR, Field SE, Fussell SJ, Green SP, Mason C, Mathew J (2011) J Org Proc Res Develop 15:1010–1017

    Google Scholar 

  56. Chambers JM, Huang DCS, Lindqvist LM, Savage GP, White JM, Rizzacasa MA (2012) J Nat Prod 75:1500–1504

    Article  CAS  Google Scholar 

  57. Scott RW, Mazzetti C, Simpson TJ, Willis CL (2012) Chem Commun 48:2639–2641

    Article  CAS  Google Scholar 

  58. Zuo Z, Ma D (2011) Angew Chem Int Ed 50:12008–12011

    Article  CAS  Google Scholar 

  59. Diebolt O, Cruzeuil C, Müller C, Vogt D (2012) Adv Synth Catal 354:670–677

    Article  CAS  Google Scholar 

  60. Vieira CG, da Silva JG, Penna CAA, dos Santos EN, Gusevskaya EV (2010) App Catal A Gen 380:125–132

    Article  CAS  Google Scholar 

  61. El Ali B, Tijani J, Fettouhi M (2005) J Mol Catal A Chem 230:9–16

    Article  Google Scholar 

  62. Peixoto AF, Pereira MM, Silva AMS, Foca CM, Bayón JC, Moreno MJSM, Beja AM, Paixão JA, Silva MR (2007) J Mol Catal A Chem 275:121–129

    Article  CAS  Google Scholar 

  63. Grünanger CU, Breit B (2010) Angew Chem Int Ed 49:967–970

    Article  Google Scholar 

  64. Ueki Y, Ito H, Usui I, Breit B (2011) Chem Eur J 17:8555–8558

    Article  CAS  Google Scholar 

  65. Abillard O, Breit B (2007) Adv Synth Catal 349:1891–1895

    Article  CAS  Google Scholar 

  66. Chercheja S (2007) Eilbarcht. Adv Synth Catal 349:1897–1905

    Article  CAS  Google Scholar 

  67. Kemme ST, Smejkal T, Breit B (2010) Chem Eur J 16:3423–3433

    Article  CAS  Google Scholar 

  68. Breit B, Zahn SK (2001) Angew Chem Int Ed 40:1910–1913

    Article  CAS  Google Scholar 

  69. Stiller J, Vorholt AJ, Ostriwski KA, Behr A, Christmann M (2012) Chem Eur J 18:9496–9499

    Article  CAS  Google Scholar 

  70. Vanier GS (2007) Synlett 131–135

    Google Scholar 

  71. Piras L, Genesio E, Ghiron C, Taddei M (2008) Synlett 1125–1128

    Google Scholar 

  72. Salvadori J, Balducci E, Zaza S, Petricci E, Taddei M (2010) J Org Chem 75:1841–1847

    Article  CAS  Google Scholar 

  73. Pizzetti M, Russo A, Petricci E (2011) Chem Eur J 17:4523–4528

    Article  CAS  Google Scholar 

  74. Kromos CM, Leadbeater NE (2007) Org Biomol Chem 5:65–68

    Article  Google Scholar 

  75. Petricci E, Mann A, Schoenfelder A, Rota A, Taddei M (2006) Org Lett 8:3725–3727

    Article  CAS  Google Scholar 

  76. Petricci E, Taddei M (2007) Chem Today 25:40–45

    CAS  Google Scholar 

  77. Petricci E, Mann A, Salvadori J, Taddei M (2007) Tetrahedron Lett 48:8501–8504

    Article  CAS  Google Scholar 

  78. Airiau E, Girard N, Pizzeti M, Salvadori J, Taddei M, Mann A (2010) J Org Chem 75:8670–8673

    Article  CAS  Google Scholar 

  79. Airiau E, Chemin C, Girard N, Lonzi G, Mann A, Petricci E, Salvadori J, Taddei M (2010) Synthesis 2901–2914

    Google Scholar 

  80. Cini E, Salvadori J, Girard N, Mann A, Salvadori J, Taddei M (2011) Synlett 199–202

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Dipartimento di Biotecnologie, Chimica e Farmacia, Università degli Studi di Siena, Via A. Moro 2, 53100, Siena, Italy

    Elena Petricci & Elena Cini

Authors
  1. Elena Petricci
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Elena Cini
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Elena Petricci .

Editor information

Editors and Affiliations

  1. Dipartimento Farmaco Chimico Tecnologico, University of Siena, Siena, Italy

    Maurizio Taddei

  2. Laboratoire d'Innovation Thérapeutique, CNRS-Université de STRASBOURG, Illkirch, France

    André Mann

Rights and permissions

Reprints and permissions

Copyright information

© 2013 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Petricci, E., Cini, E. (2013). Domino Reactions Triggered by Hydroformylation. In: Taddei, M., Mann, A. (eds) Hydroformylation for Organic Synthesis. Topics in Current Chemistry, vol 342. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2013_463

Download citation

Publish with us

Policies and ethics

Search

Navigation