Skip to main content
SpringerLink
Log in

Catalytic Transformations Involving the Activation of sp2 Carbon–Oxygen Bonds

  • Chapter
  • First Online:
Book cover Inventing Reactions

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 44))

Abstract

This review describes transition metal-catalyzed transformations of conventionally unemployed C(sp2)–O bonds, specifically those of aryl and alkenyl ethers, carboxylates, and carbamates. Nickel-based catalysts are among the most intensively studied in this context, allowing for direct coupling using phenol- and enol-derived electrophiles. Reactions using other metals (Ru, Fe, and Rh) are also presented. The synthetic utility of these C–O bond activation reactions is illustrated in the synthesis of several elaborated molecules, especially through the orthogonal cross-couplings and oxygen-directed functionalization/C–O activation tandem.

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. Tsuji J (2004) Palladium reagents and catalysts. Wiley, Chichester

    Book  Google Scholar 

  2. Miyaura N (ed) (2001) Top Curr Chem 219

    Google Scholar 

  3. de Meijere A, Diederich F (2004) Metal-catalyzed cross-coupling reactions, 2nd edn. Wiley, Weinheim

    Book  Google Scholar 

  4. Surry DS, Buchwald SL (2008) Angew Chem Int Ed 120:6438

    Article  Google Scholar 

  5. Hartwig JF (2008) Acc Chem Res 41:1534

    Article  CAS  Google Scholar 

  6. Tyman JHP (1996) Synthetic and natural phenols. Elsevier, Amsterdam

    Google Scholar 

  7. Rappoport Z (ed) (2003) The chemistry of phenols. Wiley, Chichester

    Google Scholar 

  8. Ritter K (1993) Synthesis 735

    Google Scholar 

  9. Yu D-G, Li B-J, Shi Z-J (2010) Acc Chem Res 43:1486

    Article  CAS  Google Scholar 

  10. Li B-J, Yu D-G, Sun C-L, Shi Z-J (2011) Chem Eur J 17:1728

    Article  CAS  Google Scholar 

  11. Rosen BM, Quasdorf KW, Wilson DA, Zhang N, Resmerita A-M, Garg NK, Percec V (2011) Chem Rev 111:1346

    Article  CAS  Google Scholar 

  12. Wenkert E, Michelotti EL, Swindell CS (1979) J Am Chem Soc 101:2246

    Article  CAS  Google Scholar 

  13. Wenkert E, Michelotti EL, Swindell CS, Tingoli M (1984) J Org Chem 49:4894

    Article  CAS  Google Scholar 

  14. Hayashi T, Katsuro Y, Kumada M (1980) Tetrahedron Lett 21:3915

    Article  CAS  Google Scholar 

  15. Wenkert E, Ferreira VF, Michelotti EL, Tingoli M (1985) J Org Chem 50:719

    Article  CAS  Google Scholar 

  16. Wadman S, Whitby R, Yeates C, Kocienski P, Cooper K (1987) J Chem Soc Chem Commun 241

    Google Scholar 

  17. Whitby R, Yeates C, Kocienski P, Costello G (1987) J Chem Soc Chem Commun 429

    Google Scholar 

  18. Kocienski P, Dixon NJ, Wadman S (1988) Tetrahedron Lett 29:2353

    Article  CAS  Google Scholar 

  19. Kocienski P, Wadmana S, Cooper K (1988) Tetrahedron Lett 29:2357

    Article  CAS  Google Scholar 

  20. Kocienski P, Love C, Whitby R, Roberts DA (1988) Tetrahedron Lett 29:2867

    Article  CAS  Google Scholar 

  21. Ducoux J-P, Le Ménez P, Kunesch N, Kunesch G, Wenkert E (1990) Tetrahedron Lett 31:2595

    Article  Google Scholar 

  22. Ducoux J-P, Le Ménez P, Kunesch N, Kunesch G, Wenkert E (1992) Tetrahedron 48:6403

    Article  CAS  Google Scholar 

  23. Tingoli M, Panunzi B, Santacroce F (1999) Tetrahedron Lett 40:9329

    Article  CAS  Google Scholar 

  24. Johnstone RAW, McLean WN (1988) Tetrahedron Lett 29:5553

    Article  CAS  Google Scholar 

  25. Brigas AF, Johnstone RAW (2000) Perkin 1:1735

    Article  Google Scholar 

  26. Dankwardt JW (2004) Angew Chem Int Ed 43:2428

    Article  CAS  Google Scholar 

  27. Fu GC (2008) Acc Chem Res 41:1555

    Article  CAS  Google Scholar 

  28. Guan B-T, Xiang S-K, Wu T, Sun Z-P, Wang B-Q, Zhao, K-Q, Shi Z-J (2008) Chem Commun 1437

    Google Scholar 

  29. Guan B-T, Xiang S-K, Wang B-Q, Sun Z-P, Wang Y, Zhao K-Q, Shi Z-J (2008) J Am Chem Soc 130:3268

    Article  CAS  Google Scholar 

  30. Taylor BLH, Swift EC, Waetzig JD, Jarvo ER (2011) J Am Chem Soc 133:389

    Article  CAS  Google Scholar 

  31. Tobisu M, Shimasaki T, Chatani N (2008) Angew Chem Int Ed 47:4866

    Article  CAS  Google Scholar 

  32. Shimasaki T, Konno Y, Tobisu M, Chatani N (2009) Org Lett 11:4890

    Article  CAS  Google Scholar 

  33. Ishizu J, Yamamoto T, Yamamoto A (1976) Chem Lett 1091

    Google Scholar 

  34. Chatani N, Tatamidani H, Ie Y, Kakiuchi F, Murai S (2001) J Am Chem Soc 123:4849

    Google Scholar 

  35. Tatamidani H, Kakiuchi F, Chatani N (2004) Org Lett 6:3597

    Article  CAS  Google Scholar 

  36. Tatamidani H, Yokota K, Kakiuchi F, Chatani N (2004) J Org Chem 69:5615

    Article  CAS  Google Scholar 

  37. Quasdorf KW, Tian X, Garg NK (2008) J Am Chem Soc 130:14422

    Article  CAS  Google Scholar 

  38. Guan B-T, Wang Y, Li B-J, Yu D-G, Shi Z-J (2008) J Am Chem Soc 130:14468

    Article  CAS  Google Scholar 

  39. Sun CL, Wang Y, Zhou X, Wu ZH, Li BJ, Guan BT, Shi ZJ (2010) Chem Eur J 16:5844

    CAS  Google Scholar 

  40. Li Z, Zhang S-L, Fu Y, Guo Q-X, Liu L (2009) J Am Chem Soc 131:8815

    Article  CAS  Google Scholar 

  41. Li B-J, Li Y-Z, Lu X-Y, Liu J, Guan B-T, Shi Z-J (2008) Angew Chem Int Ed 47:10124

    Article  CAS  Google Scholar 

  42. Kocienski P, Dixon N (1989) Synlett 52

    Google Scholar 

  43. Porée F-H, Clavel A, Betzer J-F, Pancrazi A, Ardisson J (2003) Tetrahedron Lett 44:7553

    Article  Google Scholar 

  44. Sengupta S, Leite M, Raslan DS, Quesnelle C, Snieckus V (1992) J Org Chem 57:4066

    Article  CAS  Google Scholar 

  45. Yoshikai N, Matsuda H, Nakamura E (2009) J Am Chem Soc 131:9590

    Article  CAS  Google Scholar 

  46. Quasdorf KW, Riener M, Petrova KV, Garg NK (2009) J Am Chem Soc 131:17748

    Article  CAS  Google Scholar 

  47. Antoft-Finch A, Blackburn T, Snieckus V (2009) J Am Chem Soc 131:17750

    Article  CAS  Google Scholar 

  48. Xu L, Li B-J, Wu Z-H, Lu X-Y, Guan B-T, Wang B-Q, Zhao K-Q, Shi Z-J (2010) Org Lett 12:884

    Article  CAS  Google Scholar 

  49. Quasdorf KW, Antoft-Finch A, Liu P, Silberstein AL, Komaromi A, Blackburn T, Ramgren SD, Houk KN, Snieckus V, Garg NK (2011) JACS 133:6352

    Article  CAS  Google Scholar 

  50. Molander GA, Beaumard F (2010) Org Lett 12:4022

    Article  CAS  Google Scholar 

  51. Yu D-G, Li B-J, Zheng S-F, Guan B-T, Wang B-Q, Shi Z-J (2010) Angew Chem Int Ed 49:4566

    Article  CAS  Google Scholar 

  52. Yu D-G, Shi Z-J (2011) Angew Chem Int Ed 50:7097

    Article  CAS  Google Scholar 

  53. Tobisu M, Shimasaki T, Chatani N (2009) Chem Lett 38:710

    Article  CAS  Google Scholar 

  54. Tobisu M, Yasutome A, Yamakawa K, Shimasaki T, Chatani N (2012) Tetrahedron 68:5157

    Google Scholar 

  55. Shimasaki T, Tobisu M, Chatani N (2010) Angew Chem Int Ed 49:2929

    Article  CAS  Google Scholar 

  56. Mesganaw T, Silberstein AL, Ramgren SD, Nathel NFF, Hong X, Liu P, Garg NK (2011) Chem Sci 2:1766

    Article  CAS  Google Scholar 

  57. Ducoux J-P, Le Ménez P, Kunesch N, Wenkert E (1993) J Org Chem 58:1290

    Article  CAS  Google Scholar 

  58. Álvarez-Bercedo P, Martin R (2010) J Am Chem Soc 132:17352

    Google Scholar 

  59. Tobisu M, Yamakawa K, Shimasaki T, Chatani N (2011) Chem Commun 47:2946

    Article  CAS  Google Scholar 

  60. Kelley P, Lin S, Edouard G, Day MW, Agapie T (2012) J Am Chem Soc 134:5480

    Article  CAS  Google Scholar 

  61. Sergeev AG, Hartwig JF (2011) Science 332:439

    Article  CAS  Google Scholar 

  62. Huang K, Yu D-G, Zheng S-F, Wu Z-H, Shi Z-J (2011) Chem Eur J 17:786

    Article  CAS  Google Scholar 

  63. Muto K, Yamaguchi J, Itami K (2012) J Am Chem Soc 134:169

    Article  CAS  Google Scholar 

  64. Ehle AR, Watson MP (2012) Org Lett 14:1202

    Article  CAS  Google Scholar 

  65. Kakiuchi F, Usui M, Ueno S, Chatani N, Murai S (2004) J Am Chem Soc 126:2706

    Article  CAS  Google Scholar 

  66. Murai S, Kakiuchi F, Sekine S, Tanaka Y, Kamatani A, Sonoda M, Chatani N (1993) Nature 366:529

    Article  CAS  Google Scholar 

  67. Ueno S, Mizushima E, Chatani N, Kakiuchi F (2006) J Am Chem Soc 128:16516

    Article  CAS  Google Scholar 

  68. Nichols JM, Bishop LM, Bergman RG, Ellman JA (2010) J Am Chem Soc 132:12554

    Article  CAS  Google Scholar 

  69. Yu J-Y, Kuwano R (2009) Angew Chem Int Ed 48:7217

    Article  CAS  Google Scholar 

  70. Lee HW, Kwong FY (2009) Synlett 3151

    Google Scholar 

  71. Yu J-Y, Shimizu R, Kuwano R (2010) Angew Chem Int Ed 49:6396

    Article  CAS  Google Scholar 

  72. Tamura M, Kochi JK (1971) J Am Chem Soc 93:1487

    Article  CAS  Google Scholar 

  73. Bolm C, Legros J, Le Paih J, Zani L (2004) Chem Rev 104:6217

    Article  CAS  Google Scholar 

  74. Sherry BD, Fürstner A (2008) Acc Chem Res 41:1500

    Article  CAS  Google Scholar 

  75. Nakamura E, Yoshikai N (2010) J Org Chem 75:6061

    Article  CAS  Google Scholar 

  76. Sun C-L, Li B-J, Shi Z-J (2010) Chem Rev 111:1293

    Article  Google Scholar 

  77. Li B-J, Xu L, Wu Z-H, Guan B-T, Sun C-L, Wang B-Q, Shi Z-J (2009) J Am Chem Soc 131:14656

    Article  CAS  Google Scholar 

  78. Matsuura Y, Tamura M, Kochi T, Sato M, Chatani N, Kakiuchi F (2007) J Am Chem Soc 129:9858

    Article  CAS  Google Scholar 

  79. Kocieński PJ, Love CJ, Whitby RJ, Costello G, Roberts DA (1989) Tetrahedron 45:3839

    Article  Google Scholar 

  80. Xiao B, Fu Y, Xu J, Gong T-J, Dai J-J, Yi J, Liu L (2010) J Am Chem Soc 132:468

    Article  CAS  Google Scholar 

  81. Snieckus V (1990) Chem Rev 90:879

    Article  CAS  Google Scholar 

  82. Chauder BA, Kalinin AV, Snieckus V (2001) Synlett 140

    Google Scholar 

  83. Silberstein AL, Ramgren SD, Garg NK (2012) Org Lett 14:3796

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka, 565-0871, Japan

    Mamoru Tobisu & Naoto Chatani

Authors
  1. Mamoru Tobisu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Naoto Chatani
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Mamoru Tobisu or Naoto Chatani .

Editor information

Editors and Affiliations

  1. , FB Chemie - Organische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Str. 54, Kaiserslautern, 67663, Germany

    Lukas J. Gooßen

Rights and permissions

Reprints and permissions

Copyright information

© 2012 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Tobisu, M., Chatani, N. (2012). Catalytic Transformations Involving the Activation of sp2 Carbon–Oxygen Bonds. In: Gooßen, L. (eds) Inventing Reactions. Topics in Organometallic Chemistry, vol 44. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_2012_42

Download citation

Publish with us

Policies and ethics

Search

Navigation