Skip to main content
SpringerLink
Log in

Gold-Catalyzed Carbene Transfer Reactions

  • Chapter
  • First Online:
Homogeneous Gold Catalysis

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 357))

Abstract

In homogeneous gold catalysis, generations and reactions of metal carbenes have been one of the most rapidly developing areas because of their diverse reactivity under mild conditions. This review covers recent advances in the gold-catalyzed oxygen atom transfer and carbene transfer reactions to alkynes. Atom transfer to an alkyne enables alkynes to function as metal carbene synthons. Many such reactions fulfill redox neutrality starting from safe and easily handled precursors.

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
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

Abbreviations

Ad:

1-Adamantyl

cat.:

Catalyst

DCE:

1,2-Dichloroethane

Dipp:

2,6-Diisopropylphenyl

dppm:

1,1-Bis(diphenylphosphino)methane

equiv.:

Equivalent

IAd:

1,3-Bis(1-adamantyl)imidazole-2-ylidene

IMes:

1,3-Bis(2,4,6-trimethylphenyl)imidazole-2-ylidene

IPr:

1,3-Bis(2,6-diisopropylphenyl)imidazole-2-ylidene

L:

Ligand

LG:

Leaving group

mCPBA:

m-Chloroperbenzoic acid

Ms:

Methanesulfonyl

OAT:

Oxygen atom transfer

pyr:

Pyridine

rt:

Room temperature

Tf:

Trifluromethanesulfonyl

References

  1. Davies HML, Beckwith REJ (2003) Chem Rev 103:2861

    Article  CAS  Google Scholar 

  2. Davies HML, Deton JR (2009) Chem Soc Rev 38:3061

    Article  CAS  Google Scholar 

  3. Fischer N, Goddard-Borger ED, Greiner R, Klapotke TM, Skelton BW, Stierstorfer J (2012) J Org Chem 77:1760

    Article  CAS  Google Scholar 

  4. Proctor LD, Warr AJ (2002) Org Process Res Dev 6:884

    Article  CAS  Google Scholar 

  5. Li X (2011) Angew Chem Int Ed 50:7226

    Article  Google Scholar 

  6. Nevado C, de Haro T (2012) Synthetic potential behind gold-catalyzed redox processes. In: Pignataro B (ed) New strategies in chemical synthesis and catalysis. Wiley, Weinheim

    Google Scholar 

  7. Yeom H-S, Shin S (2014) Acc Chem Res 47:966

    Article  CAS  Google Scholar 

  8. Zhang L (2014) Acc Chem Res 47:877

    Article  CAS  Google Scholar 

  9. Marion N, Nolan SP (2007) Angew Chem Int Ed 46:2750

    Article  CAS  Google Scholar 

  10. Mauleon P, Toste FD (2012) Gold-catalyzed reactions of propargyl esters, proparyl alcohols, and related compounds. In: Hashmi ASK, Toste FD (eds) Modern gold catalyzed synthesis. Wiley, Weinheim

    Google Scholar 

  11. Miege F, Meyer C, Cossy J (2011) Beilstein J Org Chem 7:717

    Article  CAS  Google Scholar 

  12. Gorin DJ, Davis NR, Toste FD (2005) J Am Chem Soc 127:11260

    Article  CAS  Google Scholar 

  13. Wetzel A, Gagosz F (2011) Angew Chem Int Ed 50:7354

    Article  CAS  Google Scholar 

  14. Lu B, Luo Y, Liu L, Ye L, Wang Y, Zhang L (2011) Angew Chem Int Ed 50:8358

    Article  CAS  Google Scholar 

  15. Shapiro ND, Toste FD (2007) J Am Chem Soc 129:4160

    Article  CAS  Google Scholar 

  16. Li C, Zhang L (2011) Org Lett 13:1738

    Article  CAS  Google Scholar 

  17. Davies PW, Cremonesi A, Dumitrescu L (2011) Angew Chem Int Ed 50:8931

    Article  CAS  Google Scholar 

  18. Witham CA, Mauleon P, Shapiro ND, Sherry BD, Toste FD (2007) J Am Chem Soc 129:5838

    Article  CAS  Google Scholar 

  19. Li G, Zhang L (2007) Angew Chem Int Ed 46:5156

    Article  CAS  Google Scholar 

  20. Xiao FP, Liu Y, Wang JB (2007) Tetrahedron Lett 48:1147

    Article  CAS  Google Scholar 

  21. Cuenca AB, Montserrat S, Hossain KM, Mancha G, Lledós A, Medio-Simón M, Ujaque G, Asensio G (2009) Org Lett 11:4906

    Article  CAS  Google Scholar 

  22. Li C-W, Pati K, Lin G-Y, Sohel SMA, Hung H-H, Liu R-S (2010) Angew Chem Int Ed 49:9891

    Article  CAS  Google Scholar 

  23. Lu B, Li Y, Wang Y, Aue DH, Luo Y, Zhang L (2013) J Am Chem Soc 135:8512

    Article  CAS  Google Scholar 

  24. Davies PW, Albrecht SJC (2009) Angew Chem Int Ed 48:8372

    Article  CAS  Google Scholar 

  25. Pirrung MC, Zhang J, Lackey K, Sternbach DS, Brown F (1995) J Org Chem 60:2112

    Article  CAS  Google Scholar 

  26. Xu H, Zhang W, Shu D, Werness JB, Tang W (2008) Angew Chem Int Ed 47:8933

    Article  CAS  Google Scholar 

  27. Xu C-F, Xu M, Jia Y-X, Li C-Y (2011) Org Lett 13:1556

    Article  CAS  Google Scholar 

  28. Hashmi ASK, Bührle M, Salathé R, Bats JW (2008) Adv Synth Catal 350:2059

    Article  CAS  Google Scholar 

  29. Lin G-Y, Li C-W, Hung S-H, Liu R-S (2008) Org Lett 10:5059

    Article  CAS  Google Scholar 

  30. Chaudhuri R, Liu R-S (2011) Adv Synth Catal 353:2589

    Article  CAS  Google Scholar 

  31. Asao N, Sato K, Yamamoto Y (2003) Tetrahedron Lett 44:5675

    Article  CAS  Google Scholar 

  32. Li X, Vogel T, Incarvito CD, Crabtree RH (2005) Organometallics 24:62

    Article  Google Scholar 

  33. Jadav AM, Bhunia S, Liao H-Y, Liu R-S (2011) J Am Chem Soc 133:1769

    Article  Google Scholar 

  34. Yeom H-S, Lee Y, Lee J-E, Shin S (2009) Org Biomol Chem 7:4744

    Article  CAS  Google Scholar 

  35. Yeom H-S, Shin S (2008) Synlett 924

    Google Scholar 

  36. Yeom H-S, Lee JE, Shin S (2008) Angew Chem Int Ed 47:7040

    Article  CAS  Google Scholar 

  37. Song G, Chen D, Su Y, Han K, Pan C-L, Jia A, Li X (2011) Angew Chem Int Ed 50:7791

    Article  CAS  Google Scholar 

  38. Jeong J, Yeom H-S, Kwon O, Shin S (2011) Chem Asian J 6:1977

    Article  CAS  Google Scholar 

  39. Yeom H-S, Lee Y, Jeong J, So E, Hwang S, Lee J-E, Shim S, Shin S (2010) Angew Chem Int Ed 49:1611

    Article  CAS  Google Scholar 

  40. Bhunia S, Chang C-J, Liu R-S (2012) Org Lett 14:5522

    Article  CAS  Google Scholar 

  41. Mukherjee A, Dateer RB, Chaudhuri R, Bhunia S, Karad SN, Liu R-S (2011) J Am Chem Soc 133:15372

    Article  CAS  Google Scholar 

  42. Cui L, Peng Y, Zhang L (2009) J Am Chem Soc 131:8394

    Article  CAS  Google Scholar 

  43. Cui L, Zhang G, Peng Y, Zhang L (2009) Org Lett 11:1225

    Article  CAS  Google Scholar 

  44. Noey EL, Luo Y, Zhang L, Houk KN (2012) J Am Chem Soc 134:1078

    Article  CAS  Google Scholar 

  45. Porzelle A, Woodrow MD, Tomkinson NCO (2009) Synlett 797

    Google Scholar 

  46. Jones KL, Porzelle A, Hall A, Woodrow MD, Tomkinson NCO (2008) Org Lett 10:797

    Article  CAS  Google Scholar 

  47. Yeom H-S, So E, Shin S (2011) Chem Eur J 17:1764

    Article  CAS  Google Scholar 

  48. Coates RM, Hutchins CW (1979) J Org Chem 44:4742

    Article  CAS  Google Scholar 

  49. Joule JA (2000) Sci Synth 10:380

    Google Scholar 

  50. Wang Y, Ye L, Zhang L (2011) Chem Commun 47:7815

    Article  CAS  Google Scholar 

  51. Wang Y, Liu L, Zhang L (2013) Chem Sci 4:739

    Article  CAS  Google Scholar 

  52. Zheng Z, Tu H, Zhang L (2014) Chem Eur J 20:2445

    Google Scholar 

  53. Kawade RK, Huang P-H, Kara SN, Liu R-S (2014) Org Biomol Chem 12:737

    Article  CAS  Google Scholar 

  54. Murru S, Gallo AA, Srivastava RS (2011) ACS Catal 1:29

    Article  CAS  Google Scholar 

  55. Pagar VV, Jadav AM, Liu R-S (2011) J Am Chem Soc 133:20728

    Article  CAS  Google Scholar 

  56. Xu Z-J, Zhu D, Zeng X, Wang F, Tan B, Hou Y, Ly Y, Zhong G (2010) Chem Commun 46:2504

    Article  CAS  Google Scholar 

  57. Abramovitch RA, Shinkai I (1974) For early use of pyridine-N-oxides. J Am Chem Soc 96:5265

    Article  CAS  Google Scholar 

  58. Caron S, Do NM, Sieser JE (2000) Tetrahedron Lett 41:2299

    Article  CAS  Google Scholar 

  59. Veerakumar P, Balakumar S, Velayudham M, Lu K-L, Rajagopal S (2012) Catal Sci Tech 2:1140

    Article  CAS  Google Scholar 

  60. Takahashi S, Kano H (1963) Tetrahedron Lett 25:1687

    Article  Google Scholar 

  61. Lee TD, Keana JFW (1976) J Org Chem 41:3237

    Article  CAS  Google Scholar 

  62. Ye L, Zhang G, Zhang L (2010) J Am Chem Soc 132:3258

    Article  CAS  Google Scholar 

  63. Ye L, He W, Zhang L (2010) J Am Chem Soc 132:8550

    Article  CAS  Google Scholar 

  64. Ye L, He W, Zhang L (2011) Angew Chem Int Ed 50:3236

    Article  CAS  Google Scholar 

  65. Robak MT, Herbage MA, Ellman JA (2010) Chem Rev 110:3600

    Article  CAS  Google Scholar 

  66. Shu C, Li L, Yu Y-F, Jiang S, Ye L-W (2014) Chem Commun 50:2522

    Article  CAS  Google Scholar 

  67. Lu B, Li C, Zhang L (2010) J Am Chem Soc 132:14070

    Article  CAS  Google Scholar 

  68. Vasu D, Hung H-H, Bhunia S, Gawade SA, Das A, Liu R-S (2011) Angew Chem Int Ed 50:6911

    Article  CAS  Google Scholar 

  69. Bhunia S, Ghorpade S, Huple DB, Liu R-S (2012) Angew Chem Int Ed 51:2939

    Article  CAS  Google Scholar 

  70. Ghorpade S, Su M-D, Liu R-S (2013) Angew Chem Int Ed 52:4229

    Article  CAS  Google Scholar 

  71. Wang Y, Ki K, Lan S, Zhang L (2012) Angew Chem Int Ed 51:1915

    Article  CAS  Google Scholar 

  72. Karad NS, Liu R-S (2014) Angew Chem Int Ed 53:5444

    Article  CAS  Google Scholar 

  73. Dubé P, Toste FD (2006) J Am Chem Soc 128:12062

    Article  Google Scholar 

  74. Pawar SK, Wang C-D, Bhunia S, Jadhav AM, Liu R-S (2013) Angew Chem Int Ed 54:7559

    Article  Google Scholar 

  75. Qian D, Zhang J (2011) Chem Commun 47:11152

    Article  CAS  Google Scholar 

  76. Yeom H-S, Shin S (2013) Org Biomol Chem 11:1189

    Article  Google Scholar 

  77. Davies PW, Cremonesi A, Martin N (2011) Chem Commun 47:379

    Article  CAS  Google Scholar 

  78. He W, Xie L, Xu Y, Xiang J, Zhang L (2012) Org Biomol Chem 10:3168

    Article  CAS  Google Scholar 

  79. Xie L, Liang Z, Yan D, He W, Xiang J (2013) Synthesis 24:1809

    CAS  Google Scholar 

  80. He W, Li C, Zhang L (2011) J Am Chem Soc 133:8482

    Article  CAS  Google Scholar 

  81. Luo Y, Ji K, Li Y, Zhang L (2012) J Am Chem Soc 134:17412

    Article  CAS  Google Scholar 

  82. Hesp KD, Stradiotto M (2010) J Am Chem Soc 132:18026

    Article  CAS  Google Scholar 

  83. Ji K, Zhao Y, Zhang L (2013) Angew Chem Int Ed 52:6508

    Article  CAS  Google Scholar 

  84. Wu G, Zheng R, Nelson J, Zhang L (2014) Adv Synth Catal 356:1229

    Article  CAS  Google Scholar 

  85. Li J, Ji K, Zheng R, Nelson J, Zhang L (2014) Chem Commun 50:4130

    Article  CAS  Google Scholar 

  86. Li L, Shu C, Zhou B, Yu Y-F, Xiao X-Y, Ye L-W (2014) Chem Sci 5:4057

    Article  CAS  Google Scholar 

  87. Ringger DH, Chen P (2013) Angew Chem Int Ed 52:4686

    Article  CAS  Google Scholar 

  88. Kramer S, Skrydstrup T (2012) Angew Chem Int Ed 51:4681

    Article  CAS  Google Scholar 

  89. Huang X, Peng B, Luparia M, Gomes LFR, Veiros LF, Maulide N (2012) Angew Chem Int Ed 51:8886

    Article  CAS  Google Scholar 

  90. Huang X, Goddard R, Maudide N (2010) Angew Chem Int Ed 49:8979

    Article  CAS  Google Scholar 

  91. Huang X, Klimczyk S, Veiros LF, Maulide N (2013) Chem Sci 4:1105

    Article  CAS  Google Scholar 

  92. Bonnaud B, Funes P, Jubault N, Vacher B (2005) Eur J Org Chem 3360

    Google Scholar 

  93. Sabbatani J, Huang X, Veiros LF, Maulide N (2014) Chem Eur J 20:10636

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by a National Research Foundation of Korea (NRF) grant funded by the Korean Government (2014-011165, 2012-015662 and 2012M3A7B4049653).

Author information

Authors and Affiliations

  1. Department of Chemistry and Center for New Directions in Organic Synthesis, Hanyang University, 133-791, Seoul, South Korea

    Seunghoon Shin

Authors
  1. Seunghoon Shin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Seunghoon Shin .

Editor information

Editors and Affiliations

  1. Department of Chemistry, University of North Texas, Denton, Texas, USA

    LeGrande M. Slaughter

Rights and permissions

Reprints and permissions

Copyright information

© 2014 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Shin, S. (2014). Gold-Catalyzed Carbene Transfer Reactions. In: Slaughter, L. (eds) Homogeneous Gold Catalysis. Topics in Current Chemistry, vol 357. Springer, Cham. https://doi.org/10.1007/128_2014_589

Download citation

Publish with us

Policies and ethics

Search

Navigation