Skip to main content

Aminations with Hypervalent Iodine

  • Chapter
  • First Online:
Hypervalent Iodine Chemistry

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 373))

Abstract

Recent progress in the area of hypervalent iodine-mediated and catalyzed amination reaction of hydrocarbons is reviewed. These reactions comprise processes under both intra and intermolecular control and include the functionalization of aromatic C–H bonds as well as conversion of sp-, sp2-, and sp3-hybridized carbon atoms. These developments demonstrate that hypervalent iodine(III) methodology has reached a high level in amination chemistry. The individual reactions are discussed with a focus on mechanistic details and emphasis is made to the underlying hypervalent iodine reagents, for which structural information is available.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
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. Zhdankin VV (2014) Hypervalent iodine chemistry. Wiley, Chichester

    Google Scholar 

  2. Koser GF (2003) In: Wirth T (ed) Hypervalent iodine chemistry. Modern developments in organic synthesis, Topic curr chem 224. Springer, Berlin/Heidelberg, pp 138–172

    Google Scholar 

  3. Samanta R, Matcha K, Antonchick AP (2013) Eur J Org Chem 5769

    Google Scholar 

  4. Narayan R, Manna S, Antonchick AP (2015) Synlett 26:1785

    Article  CAS  Google Scholar 

  5. Cho SH, Yoon J, Chang S (2011) J Am Chem Soc 133:5996

    Article  CAS  Google Scholar 

  6. Antonchick AP, Samanta R, Kulikov K, Lategahn J (2011) Angew Chem Int Ed 50:8605

    Article  CAS  Google Scholar 

  7. Ban X, Pan Y, Lin Y, Wang S, Du Y, Zhao K (2012) Org Biomol Chem 10:3606

    Article  CAS  Google Scholar 

  8. Du Y, Liu R, Linn G, Zhao K (2006) Org Lett 8:5919

    Article  CAS  Google Scholar 

  9. Fra L, Millán E, Souto JA, Muñiz K (2014) Angew Chem Int Ed 53:7349

    Article  CAS  Google Scholar 

  10. Huang J, He Y, Wang Y, Zhu Q (2012) Chem Eur J 18:13964

    Article  CAS  Google Scholar 

  11. Alla SK, Kumar RK, Sadhu P, Punniyamurthy T (2013) Org Lett 15:1334

    Article  CAS  Google Scholar 

  12. Chi Y, Zhang W-X, Xi Z (2014) Org Lett 16:6274

    Article  CAS  Google Scholar 

  13. Maiti S, Mal P (2015) Adv Synth Catal 357:1416

    Article  CAS  Google Scholar 

  14. He Y, Huang J, Liang D, Liu L, Zhu Q (2013) Chem Commun 49:7352

    Article  CAS  Google Scholar 

  15. Liang D, He Y, Liu L, Zhu Q (2013) Org Lett 15:3476

    Article  CAS  Google Scholar 

  16. Wang H, Wang Y, Peng C, Zhang J, Zhu Q (2010) J Am Chem Soc 132:13217

    Article  CAS  Google Scholar 

  17. Chu J-H, Hsu W-T, Wu Y-H, Chaing M-F, Hsu N-H, Huang H-P, Wu J (2014) J Org Chem 79:11395

    Article  CAS  Google Scholar 

  18. Dohi T, Maruyama A, Minamitsuji Y, Takenaga T, Kita Y (2007) Chem Commun 43:1224

    Article  Google Scholar 

  19. Dohi T, Takenaga N, Fukushima K-I, Uchiyama T, Kato D, Shiro M, Fujioka H, Kita Y (2010) Chem Commun 46:7697

    Article  CAS  Google Scholar 

  20. Kim HJ, Kim J, Cho H, Chang S (2011) J Am Chem Soc 133:16382

    Article  CAS  Google Scholar 

  21. Kantak AA, Potavathri S, Barham RA, Romano KM, DeBoef B (2011) J Am Chem Soc 133:19960

    Article  CAS  Google Scholar 

  22. Moriyama K, Ishida K, Togo H (2012) Org Lett 14:946

    Article  CAS  Google Scholar 

  23. Itoh N, Sakamoto T, Miyazawa E, Kikugawa Y (2002) J Org Chem 67:7424

    Article  Google Scholar 

  24. Samantha R, Lategahn I, Antonchick AP (2012) Chem Commun 48:3194

    Article  Google Scholar 

  25. Souto JA, Martínez C, Velilla I, Muñiz K (2013) Angew Chem Int Ed 52:1324

    Article  CAS  Google Scholar 

  26. Samantha R, Bauer JO, Strohmann C, Antonchick AP (2012) Org Lett 14:5518

    Article  Google Scholar 

  27. Manna S, Serebrennikova PO, Utepova IA, Antonchick AP (2015) Org Lett 17:4588

    Article  CAS  Google Scholar 

  28. Ivanov AS, Popov IA, Boldyrev AI, Zhdankin VV (2014) Angew Chem Int Ed 53:9617

    Article  CAS  Google Scholar 

  29. Macikenas D, Skrypczak-Jankun E, Protasiewicz JD (1999) J Am Chem Soc 121:7164

    Article  CAS  Google Scholar 

  30. Meprathu BV, Protasiewicz JD (2010) Tetrahedron 66:5768

    Article  CAS  Google Scholar 

  31. Meprathu BV, Protasiewicz JD (2003) Arkivoc VI:83

    Google Scholar 

  32. Yoshimura A, Nemykin VN, Zhdankin VV (2011) Chem Eur J 17:10538

    Article  CAS  Google Scholar 

  33. Müller P (1997) Adv Catal Processes 2:113

    Article  Google Scholar 

  34. Padwa A, Stengel T (2002) Org Lett 4:2137

    Article  CAS  Google Scholar 

  35. Moriarty RM, Tyagi S (2010) Org Lett 12:364

    Article  CAS  Google Scholar 

  36. Liu Z-G, Cheng H, Ge M-J, Xu L, Wang F-P (2013) Tetrahedron 69:5431

    Article  CAS  Google Scholar 

  37. Mei R-H, Liu Z-G, Cheng H, Xu L, Wang F-P (2013) Org Lett 15:2206

    Article  CAS  Google Scholar 

  38. Li J, Liang J-L, Chan PWH, Che C-M (2005) Org Lett 7:5801

    Article  CAS  Google Scholar 

  39. Li J, Liang J-L, Chan PWH, Che C-M (2004) Tetrahedron Lett 45:2685

    Article  CAS  Google Scholar 

  40. Richardson RD, Desaize M, Wirth T (2007) Chem Eur J 13:6745

    Article  CAS  Google Scholar 

  41. Ochiai M, Kaneaki T, Tada N, Miyamoto K, Chuman H, Shiro M, Hayashi S, Nakanishi W (2007) J Am Chem Soc 129:12938

    Article  CAS  Google Scholar 

  42. Ochiai M, Miyamoto K, Kaneaki T, Hayashi S, Nakanishi W (2011) Science 332:448

    Article  CAS  Google Scholar 

  43. Muñiz K (2014) In: Molander G, Knochel P (eds) Comprehensive organic synthesis II, vol 7. Elsevier, Oxford, 411 p

    Google Scholar 

  44. Romero M, Wöste TH, Muñiz K (2014) Chem Asian J 9:950

    Article  Google Scholar 

  45. Singh FV, Wirth T (2014) Chem Asian J 9:950

    Article  CAS  Google Scholar 

  46. Liang H, Ciufolini MA (2011) Angew Chem Int Ed 50:11849

    Article  CAS  Google Scholar 

  47. Correa A, Tellitu I, Domínguez E, SanMartin R (2006) J Org Chem 71:8316

    Article  CAS  Google Scholar 

  48. Tellitu I, Domínguez E (2011) Trends Heterocycl Chem 15:23

    CAS  Google Scholar 

  49. Wardrop DJ, Bowen EG (2011) Org Lett 13:2376

    Article  CAS  Google Scholar 

  50. Bowen EG, Wardrop DJ (2010) Org Lett 12:5330

    Article  CAS  Google Scholar 

  51. Cochran BM, Michael FE (2008) Org Lett 10:5039

    Article  CAS  Google Scholar 

  52. Lovick HM, Michael FE (2010) J Am Chem Soc 132:1249

    Article  CAS  Google Scholar 

  53. Chen H, Kaga A, Chiba S (2014) Org Lett 16:6136

    Article  CAS  Google Scholar 

  54. Farid U, Wirth T (2012) Angew Chem Int Ed 51:3462

    Article  CAS  Google Scholar 

  55. Kong W, Beige P, de Haro T, Nevado C (2013) Angew Chem Int Ed 52:2469

    Article  CAS  Google Scholar 

  56. Wang Q, Zhong W, Wei X, Ning M, Mang X, Li Z (2012) Org Biomol Chem 10:8566

    Article  CAS  Google Scholar 

  57. Liu G-Q, Li Y-M (2014) J Org Chem 79:10094

    Article  CAS  Google Scholar 

  58. Moriarty RM, Khosrowshahi JS (1986) Tetrahedron Lett 27:2809

    Article  CAS  Google Scholar 

  59. Magnus P, Lacour J, Evans PA, Roe MB, Hulme C (1996) J Am Chem Soc 118:3406

    Article  CAS  Google Scholar 

  60. Magnus P, Lacour J (1992) J Am Chem Soc 114:767

    Article  CAS  Google Scholar 

  61. Magnus P, Lacour J (1992) J Am Chem Soc 114:3993

    Article  CAS  Google Scholar 

  62. Magnus P, Roe MB, Hulme C (1995) Chem Commun 263

    Google Scholar 

  63. Martínez C, Muñiz K (2013) J Org Chem 78:2168

    Article  Google Scholar 

  64. Yang H-T, Lu X-W, Xing M-L, Sun X-Q, Miao C-B (2014) Org Lett 16:5882

    Article  CAS  Google Scholar 

  65. Röben C, Souto JA, González Y, Lishchynskyi A, Muñiz K (2011) Angew Chem Int Ed 50:9478

    Article  Google Scholar 

  66. Souto JA, González Y, Iglesias A, Zian D, Lishchynskyi A, Muñiz K (2012) Chem Asian J 7:1103

    Article  CAS  Google Scholar 

  67. Kong A, Blakey SB (2012) Synthesis 44:1190

    Article  CAS  Google Scholar 

  68. Röben C, Souto JA, Escudero-Adán E, Muñiz K (2013) Org Lett 15:1008

    Article  Google Scholar 

  69. Hong KB, Johnston JN (2014) Org Lett 16:3804

    Article  CAS  Google Scholar 

  70. Danneman MW, Hong KB, Johnston JN (2015) Org Lett 17:2558

    Article  CAS  Google Scholar 

  71. Danneman MW, Hong KB, Johnston JN (2015) Org Lett 17:3806

    Article  CAS  Google Scholar 

  72. Lishchynskyi A, Muñiz K (2012) Chem Eur J 18:2213

    Article  Google Scholar 

  73. Purkait N, Okumura S, Souto JA, Muñiz K (2014) Org Lett 16:4750

    Article  CAS  Google Scholar 

  74. Yoshimura A, Koski SR, Fuchs JM, Saito A, Nemykin VN, Zhdankin VV (2015) Chem Eur J 21:5328

    Article  CAS  Google Scholar 

  75. Mao L, Li Y, Xiong T, Sun K, Zhang Q (2013) J Org Chem 78:733

    Article  CAS  Google Scholar 

  76. Souto JA, Zian D, Muñiz K (2012) J Am Chem Soc 134:7242

    Article  CAS  Google Scholar 

  77. Kiyokawa K, Yahata S, Kojima T, Minakata S (2014) Org Lett 16:4646

    Article  CAS  Google Scholar 

  78. Souto J, Becker P, Iglesias A, Muñiz K (2012) J Am Chem Soc 134:15505

    Article  CAS  Google Scholar 

  79. Nagashima K, Sakamoto T, Kikugawa Y (2007) Heterocycles 74:273

    Article  CAS  Google Scholar 

  80. Hernández R, Rivera A, Salazar JA, Suárez E (1980) Chem Commun 958

    Google Scholar 

  81. Betancor C, Concepción JI, Hernández R, Salazar JA, Suárez E (1983) J Org Chem 48:4430

    Article  CAS  Google Scholar 

  82. De Armas P, Carrau R, Concepción JI, Francisco CG, Hernández R, Suárez E (1985) Tetrahedron Lett 26:2493

    Article  Google Scholar 

  83. Carrau R, Hernández R, Suárez E, Betancor C (1987) Perkin Trans 1 937

    Google Scholar 

  84. De Armas P, Francisco CG, Hernández R, Salazar JA, Suárez E (1988) Perkin Trans 1 3255

    Google Scholar 

  85. Fan R, Pu D, Wen F, Wu J (2007) J Org Chem 72:8994

    Article  CAS  Google Scholar 

  86. Kim YR, Cho S, Lee PH (2014) Org Lett 16:3098

    Article  CAS  Google Scholar 

  87. Martínez C, Muñiz K (2015) Angew Chem Int Ed 54:8287

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Kilian Muñiz .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Muñiz, K. (2015). Aminations with Hypervalent Iodine. In: Wirth, T. (eds) Hypervalent Iodine Chemistry. Topics in Current Chemistry, vol 373. Springer, Cham. https://doi.org/10.1007/128_2015_663

Download citation

Publish with us

Policies and ethics