Skip to main content
SpringerLink
Log in

Synthesis of Heterocycles via Radical Carbonylation

  • Chapter
  • First Online:
Transition Metal Catalyzed Carbonylative Synthesis of Heterocycles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 42))

Abstract

Alkyl, aryl, and alkenyl radicals react with CO to form the corresponding acyl radicals, which serve as key intermediates for the synthesis of a wide variety of carbonyl compounds. This chapter focuses on the applications of radical carbonylation for the synthesis of heterocyclic compounds. Radical carbonylation process is reliable for alkyl substrates, since alkyl radicals are sufficiently stable to isomerization unlike rather instable alkyl Pd species. Acyl radicals, key intermediates in the radical carbonylation, have both nucleophilic and electrophilic characters, depending on the attacking reagents and the electrophilic nature is particularly useful to achieve synthesis of nitrogen-containing heterocycles by the reactions with imines, amines, azides, and amidines.

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 129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
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. Beller M (2006) Catalytic carbonylation reactions , vol 18, Topics in Organometallic Chemistry. Springer, Berlin/Heidelberg

    Book  Google Scholar 

  2. Kollár L (2008) Modern carbonylation methods. Wiley, Weinheim

    Book  Google Scholar 

  3. Fukuyama T, Maetani S, Ryu I (2014) Carbonylation and decarbonylation reactions. In: Molander GA, Knochel P (eds) Comprehensive organic synthesis, vol 3, 2nd edn. Elsevier, Oxford, pp 1073–1100

    Chapter  Google Scholar 

  4. Ryu I, Kusano K, Ogawa A, Kambe N, Sonoda N (1990) J Am Chem Soc 112:1295

    Article  CAS  Google Scholar 

  5. Ryu I, Sonoda N (1996) Angew Chem Int Ed Engl 35:1050

    Article  Google Scholar 

  6. Ryu I, Sonoda N, Curran DP (1996) Chem Rev 96:177

    Article  CAS  Google Scholar 

  7. Ryu I (2001) Chem Soc Rev 30:16

    Article  CAS  Google Scholar 

  8. Ryu I (2002) Chem Rec 2:249

    Article  CAS  Google Scholar 

  9. Chatgilialogu C, Crich D, Komatsu M, Ryu I (1999) Chem Rev 99:1991

    Article  Google Scholar 

  10. Ryu I, Kusano K, Hasegawa M, Kambe N, Sonoda N (1991) J Chem Soc Chem Commun 1018

    Google Scholar 

  11. Berlin S, Ericsson C, Engman L (2002) Org Lett 4:3

    Article  CAS  Google Scholar 

  12. Berlin S, Ericsson C, Engman L (2003) J Org Chem 68:8386

    Article  CAS  Google Scholar 

  13. Ryu I, Kusano K, Yamazaki H, Sonoda N (1991) J Org Chem 56:5003

    Article  CAS  Google Scholar 

  14. Ryu I, Hasegawa M, Kurihara A, Ogawa A, Tsunoi S, Sonoda N (1993) Synlett 143

    Google Scholar 

  15. Ryu I, Nagahara K, Yamazaki H, Tsunoi T, Sonoda N (1994) Synlett 643

    Google Scholar 

  16. Nagahara K, Ryu I, Yamazaki H, Kambe N, Komatsu M, Sonoda N, Baba A (1997) Tetrahedron 53:14615

    Article  CAS  Google Scholar 

  17. Kishimoto Y, Ikariya T (2000) J Org Chem 65:7656

    Article  CAS  Google Scholar 

  18. Curran DP, Xu J, Lazzarini E (1995) J Chem Soc Perkin Trans 1 3049

    Google Scholar 

  19. Ryu I, Yamazaki H, Kusano K, Ogawa A, Sonoda N (1991) J Am Chem Soc 113:8558

    Article  CAS  Google Scholar 

  20. Ryu I, Yamazaki H, Ogawa A, Kambe N, Sonoda N (1993) J Am Chem Soc 115:1187

    Article  CAS  Google Scholar 

  21. Miranda LD, Cruz-Almanza R, Pavón M, Alva E, Muchowski JM (1999) Tetrahedron Lett 40:7153

    Article  CAS  Google Scholar 

  22. Tsunoi S, Ryu I, Yamazaki S, Fukushima H, Tanaka M, Komatsu M, Sonoda N (1996) J Am Chem Soc 118:10670

    Article  CAS  Google Scholar 

  23. Matsubara H, Ryu I, Schiesser CH (2007) Org Biomol Chem 5:3320

    Article  CAS  Google Scholar 

  24. Nagahara K, Ryu I, Komatsu M, Sonoda N (1997) J Am Chem Soc 119:5465

    Article  CAS  Google Scholar 

  25. Ryu I, Nagahara K, Kambe N, Sonoda N, Kreimerman M, Komatsu M (1998) Chem Commun 1953

    Google Scholar 

  26. Kreimerman S, Ryu I, Minakata S, Komatsu M (2000) Org Lett 2:389

    Article  CAS  Google Scholar 

  27. Kreimerman S, Ryu I, Minakata S, Komatsu M (2001) C R Acad Sci Paris Chim 4:497

    CAS  Google Scholar 

  28. Sumino S, Fusano A, Fukuyama T, Ryu I (2014) Acc Chem Res 47:1563

    Article  CAS  Google Scholar 

  29. Fukuyama T, Nishitani S, Inouye T, Morimoto K, Ryu I (2006) Org Lett 8:1383

    Article  CAS  Google Scholar 

  30. Fusano A, Sumino S, Fukuyama T, Ryu I (2011) Org Lett 13:2114

    Article  CAS  Google Scholar 

  31. Fusano A, Sumino S, Nishitani S, Inouye T, Morimoto K, Fukuyama T, Ryu I (2012) Chem Eur J 18:9415

    Article  CAS  Google Scholar 

  32. Tsunoi S, Ryu I, Sonoda N (1994) J Am Chem Soc 116:5473

    Article  CAS  Google Scholar 

  33. Tsunoi S, Ryu I, Okuda T, Tanaka M, Komatsu M, Sonoda N (1998) J Am Chem Soc 120:8672

    Article  Google Scholar 

  34. Tsunoi S, Ryu I, Tamura Y, Yamasaki S, Sonoda N (1994) Synlett 1009

    Google Scholar 

  35. Ryu I, Okuda T, Nagahara K, Kambe N, Komatsu M, Sonoda N (1997) J Org Chem 62:7550

    Article  CAS  Google Scholar 

  36. Studer A, Amrein S, Matsubara H, Schiesser CH, Doi T, Kawamura T, Fukuyama T, Ryu I (2003) Chem Commun 1190

    Google Scholar 

  37. Ryu I, Matsu K, Minakata S, Komatsu M (1998) J Am Chem Soc 120:5838

    Article  CAS  Google Scholar 

  38. Falzon CT, Ryu I, Schiesser CH (2002) Chem. Commun 2338

    Google Scholar 

  39. Matsubara H, Falzon C, Ryu I, Schiesser CH (2006) Org Biomol Chem 4:1920

    Article  CAS  Google Scholar 

  40. Kyne SH, Lin CY, Ryu I, Coote ML, Schiesser CH (2010) Chem Commun 46:6521

    Article  CAS  Google Scholar 

  41. Schiesser CH, Wille U, Matsubara H, Ryu I (2007) Acc Chem Res 40:303

    Article  CAS  Google Scholar 

  42. Ryu I, Miyazato H, Kuriyama H, Matsu K, Tojino M, Fukuyama T, Minakata S, Komatsu M (2003) J Am Chem Soc 125:5632

    Article  CAS  Google Scholar 

  43. Tojino M, Otsuka N, Fukuyama T, Matsubara H, Schiesser CH, Kuriyama H, Miyazato H, Minakata S, Komatsu M, Ryu I (2003) Org Biomol Chem 1:4262

    Article  CAS  Google Scholar 

  44. Tojino M, Otsuka N, Fukuyama T, Matsubara H, Ryu I (2006) J Am Chem Soc 128:7712

    Article  CAS  Google Scholar 

  45. Matsubara H, Ryu I, Schiesser CH (2005) J Org Chem 70:3610

    Article  CAS  Google Scholar 

  46. Ryu I, Uenoyama Y, Matsubara H (2006) Bull Chem Soc Jpn 79:1476

    Article  CAS  Google Scholar 

  47. Tojino M, Uenoyama Y, Fukuyama T, Ryu I (2004) Chem. Commun 2482

    Google Scholar 

  48. Ryu I, Fukuyama T, Tojino M, Uenoyama Y, Yonamine Y, Terasoma N, Matsubara H (2011) Org Biomol Chem 9:3780

    Article  CAS  Google Scholar 

  49. Ryu I, Fukuyama T, Nobuta O, Uenoyama Y (2010) Bull Kor Chem Soc 31:545

    Article  CAS  Google Scholar 

  50. Uenoyama Y, Fukuyama T, Ryu I (2007) Org Lett 9:935

    Article  CAS  Google Scholar 

  51. Fukuyama T, Nakashima N, Okada T, Ryu I (2013) J Am Chem Soc 135:1006

    Article  CAS  Google Scholar 

  52. Ueda M, Uenoyama Y, Terasoma N, Doi S, Kobayashi S, Ryu I, Murphy JA, Beilstein J (2013) Org Chem 9:1340

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Graduate School of Science, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Osaka, 599-8531, Japan

    Ilhyong Ryu & Takahide Fukuyama

Authors
  1. Ilhyong Ryu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Takahide Fukuyama
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ilhyong Ryu .

Editor information

Editors and Affiliations

  1. Department of Chemistry; Leibniz-Institut für Katalyse, Zhejiang Sci-Tech University; e.V. an der UniversitätRostock, Rostock, Germany

    Xiao-Feng Wu

  2. Leibniz-Institut für Katalyse, e.V. an der Universität Rostock, Rostock, Germany

    Matthias Beller

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Ryu, I., Fukuyama, T. (2015). Synthesis of Heterocycles via Radical Carbonylation. In: Wu, XF., Beller, M. (eds) Transition Metal Catalyzed Carbonylative Synthesis of Heterocycles. Topics in Heterocyclic Chemistry, vol 42. Springer, Cham. https://doi.org/10.1007/7081_2015_164

Download citation

Publish with us

Policies and ethics

Search

Navigation