Advertisement

Organoiodine(III) Reagents as Active Participants and Ligands in Transition Metal-Catalyzed Reactions: Iodosylarenes and (Imino)iodoarenes

  • John D. ProtasiewiczEmail author
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 373)

Abstract

This chapter overviews the roles of transition metal complexes having the organoiodine(III) reagents iodosylarenes (ArIO) and (imino)iodoarenes (ArINR) as ligands in catalysis. Mechanistic implications are discussed.

Keywords

Atom and group transfer Catalysis Hypervalent iodine Structure Transition metal complexes 

References

  1. 1.
    Varvoglis A (1992) The organic chemistry of polycoordinated iodine. VCH, New YorkGoogle Scholar
  2. 2.
    Stang PJ, Zhdankin VV (1996) Chem Rev 96:1123–1178CrossRefGoogle Scholar
  3. 3.
    Wirth T, Hirt UH (1999) Synthesis 1271–1287Google Scholar
  4. 4.
    Zhdankin VV, Stang PJ (2002) Chem Rev 102:2523–2584CrossRefGoogle Scholar
  5. 5.
    Zhdankin VV, Stang PJ (2008) Chem Rev 108:5299–5358CrossRefGoogle Scholar
  6. 6.
    Varvoglis A (2010) Tetrahedron 66:5739–5744CrossRefGoogle Scholar
  7. 7.
    Moriarty RM (2005) J Org Chem 70:2893–2903CrossRefGoogle Scholar
  8. 8.
    Brand JP, Gonzalez DF, Nicolai S, Waser J (2011) Chem Commun 47:102–115CrossRefGoogle Scholar
  9. 9.
    Charpentier J, Fruh N, Togni A (2015) Chem Rev 115:650–682CrossRefGoogle Scholar
  10. 10.
    Deprez NR, Sanford MS (2007) Inorg Chem 46:1924–1935CrossRefGoogle Scholar
  11. 11.
    Hartrampf F, Toombs-Ruane H (2015) Aust J Chem 68:699–702CrossRefGoogle Scholar
  12. 12.
    Merritt EA, Olofsson B (2009) Angew Chem Int Ed 48:9052–9070CrossRefGoogle Scholar
  13. 13.
    Neufeldt SR, Sanford MS (2012) Acc Chem Res 45:936–946CrossRefGoogle Scholar
  14. 14.
    Sharma A, Hartwig JF (2015) Nature 517:600–604CrossRefGoogle Scholar
  15. 15.
    Shu Z, Ji W, Wang X, Zhou Y, Zhang Y, Wang J (2014) Angew Chem Int Ed 53:2186–2189CrossRefGoogle Scholar
  16. 16.
    Diaz-Requejo MM, Caballero A, Fructos MR, Perez PJ (2012) Catal Met Complexes 38:229–264CrossRefGoogle Scholar
  17. 17.
    Lucas HJ, Kennedy ER, Formo MW, Johnson JR (1942) Org Synth 22:72–75CrossRefGoogle Scholar
  18. 18.
    Bressan M, Morvillo A (1989) Inorg Chem 28:950–953CrossRefGoogle Scholar
  19. 19.
    Nappa MJ, Tolman CA (1985) Inorg Chem 24:4711–4719CrossRefGoogle Scholar
  20. 20.
    Carmalt CJ, Crossley JG, Knight JG, Lightfoot P, Martin A, Muldowney MP, Norman NC, Orpen AG (1994) J Chem Soc Chem Commun 2367–2368Google Scholar
  21. 21.
    Mishra AK, Olmstead MM, Ellison JJ, Power PP (1995) Inorg Chem 34:3210–3214CrossRefGoogle Scholar
  22. 22.
    Zhdankin VV, Protasiewicz JD (2014) Coord Chem Rev 275:54–62CrossRefGoogle Scholar
  23. 23.
    Liang H, Ciufolini MA (2011) Angew Chem Int Ed 50:11849–11851CrossRefGoogle Scholar
  24. 24.
    Parra A, Reboredo S (2013) Chem - Eur J 19:17244–17260CrossRefGoogle Scholar
  25. 25.
    Ortiz de Montellano PR (2010) Chem Rev 110:932–948CrossRefGoogle Scholar
  26. 26.
    Groves JT, Kruper WJ Jr (1979) J Am Chem Soc 101:7613–7615CrossRefGoogle Scholar
  27. 27.
    Groves JT, Kruper WJ Jr, Haushalter RC (1980) J Am Chem Soc 102:6375–6377CrossRefGoogle Scholar
  28. 28.
    Hill CL, Schardt BC (1980) J Am Chem Soc 102:6374–6375CrossRefGoogle Scholar
  29. 29.
    Smegal JA, Hill CL (1983) J Am Chem Soc 105:2920–2922CrossRefGoogle Scholar
  30. 30.
    Smegal JA, Schardt BC, Hill CL (1983) J Am Chem Soc 105:3510–3515CrossRefGoogle Scholar
  31. 31.
    Birchall T, Smegal JA, Hill CL (1984) Inorg Chem 23:1910–1913CrossRefGoogle Scholar
  32. 32.
    Franklin CC, VanAtta RB, Tai AF, Valentine JS (1984) J Am Chem Soc 106:814CrossRefGoogle Scholar
  33. 33.
    Tai AF, Margerum LD, Valentine JS (1986) J Am Chem Soc 108:5006–5008CrossRefGoogle Scholar
  34. 34.
    Mashiko T, Dolphin D, Nakano T, Traylor TG (1985) J Am Chem Soc 107:3735–3736CrossRefGoogle Scholar
  35. 35.
    Volz H, Barth T (1989) Liebigs Ann Chem 171–175Google Scholar
  36. 36.
    Volz H, Mueller W (1992) Liebigs Ann Chem 1097–1101Google Scholar
  37. 37.
    Nam W, Valentine JS (1990) J Am Chem Soc 112:4977–4979CrossRefGoogle Scholar
  38. 38.
    Nam W, Valentine JS (1991) J Am Chem Soc 113:7449CrossRefGoogle Scholar
  39. 39.
    Yang Y, Diederich F, Valentine JS (1991) J Am Chem Soc 113:7195CrossRefGoogle Scholar
  40. 40.
    Nam W, Baek SJ, Liao KI, Valentine JS (1994) Bull Korean Chem Soc 15:1112–1118Google Scholar
  41. 41.
    Nam W, Valentine JS (1993) J Am Chem Soc 115:1772–1778CrossRefGoogle Scholar
  42. 42.
    Machii K, Watanabe Y, Morishima I (1995) J Am Chem Soc 117:6691–6697CrossRefGoogle Scholar
  43. 43.
    Jin R, Cho CS, Jiang LH, Shim SC (1997) J Mol Catal A Chem 116:343–347CrossRefGoogle Scholar
  44. 44.
    Feichtinger D, Plattner DA (1997) Angew Chem Int Ed Engl 36:1718–1719CrossRefGoogle Scholar
  45. 45.
    Bryliakov KP, Babushkin DE, Talsi EP (2000) Mendeleev Commun 1–3Google Scholar
  46. 46.
    Collman JP, Chien AS, Eberspacher TA, Brauman JI (2000) J Am Chem Soc 122:11098–11100CrossRefGoogle Scholar
  47. 47.
    Nam W, Lim MH, Lee HJ, Kim C (2000) J Am Chem Soc 122:6641–6647CrossRefGoogle Scholar
  48. 48.
    Adam W, Roschmann KJ, Saha-Möller CR, Seebach D (2002) J Am Chem Soc 124:5068–5073CrossRefGoogle Scholar
  49. 49.
    Nam W, Choi SK, Lim MH, Rohde J-U, Kim I, Kim J, Kim C, Que L Jr (2003) Angew Chem Int Ed 42:109–111CrossRefGoogle Scholar
  50. 50.
    Song WJ, Sun YJ, Choi SK, Nam W (2006) Chem - Eur J 12:130–137CrossRefGoogle Scholar
  51. 51.
    Collman JP, Zeng L, Brauman JI (2004) Inorg Chem 43:2672–2679CrossRefGoogle Scholar
  52. 52.
    Wang SH, Mandimutsira BS, Todd R, Ramdhanie B, Fox JP, Goldberg DP (2004) J Am Chem Soc 126:18–19CrossRefGoogle Scholar
  53. 53.
    Leeladee P, Goldberg DP (2010) Inorg Chem 49:3083–3085CrossRefGoogle Scholar
  54. 54.
    Bryliakov KP, Talsi EP (2004) Angew Chem Int Ed 43:5228–5230CrossRefGoogle Scholar
  55. 55.
    Macikenas D, Skrzypczak-Jankun E, Protasiewicz JD (1999) J Am Chem Soc 121:7164–7165CrossRefGoogle Scholar
  56. 56.
    Macikenas D, Skrzypczak-Jankun E, Protasiewicz JD (2000) Angew Chem Int Ed Engl 11:2007–2010CrossRefGoogle Scholar
  57. 57.
    Collman JP, Zeng L, Wang HJH, Lei A, Brauman JI (2006) Eur J Org Chem 2707–2714Google Scholar
  58. 58.
    Kim SJ, Latifi R, Kang HY, Nam W, de Visser SP (2009) Chem Commun 1562–1564Google Scholar
  59. 59.
    Ottenbacher RV, Bryliakov KP, Talsi EP (2010) Inorg Chem 49:8620–8628CrossRefGoogle Scholar
  60. 60.
    Pfaff FF, Kundu S, Risch M, Pandian S, Heims F, Pryjomska-Ray I, Haack P, Metzinger R, Bill E, Dau H, Comba P, Ray K (2011) Angew Chem Int Ed 50:1711–1715CrossRefGoogle Scholar
  61. 61.
    Guo M, Dong H, Li J, Cheng B, Huang Y-q, Feng Y-q, Lei A (2012) Nat Commun 3:2196/2191–2196/2199Google Scholar
  62. 62.
    Lennartson A, McKenzie CJ (2012) Angew Chem Int Ed 51:6767–6770CrossRefGoogle Scholar
  63. 63.
    Wang C, Kurahashi T, Fujii H (2012) Angew Chem Int Ed 51:7809–7811CrossRefGoogle Scholar
  64. 64.
    Wang C, Kurahashi T, Inomata K, Hada M, Fujii H (2013) Inorg Chem 52:9557–9566CrossRefGoogle Scholar
  65. 65.
    Turlington CR, Morris J, White PS, Brennessel WW, Jones WD, Brookhart M, Templeton JL (2014) Organometallics 33:4442–4448CrossRefGoogle Scholar
  66. 66.
    Turlington CR, White PS, Brookhart M, Templeton JL (2015) J Organomet Chem 792:81–87CrossRefGoogle Scholar
  67. 67.
    Hong S, Wang B, Seo MS, Lee Y-M, Kim MJ, Kim HR, Ogura T, Garcia-Serres R, Clemancey M, Latour J-M, Nam W (2014) Angew Chem Int Ed 53:6388–6392CrossRefGoogle Scholar
  68. 68.
    Wang B, Lee Y-M, Seo MS, Nam W (2015) Angew Chem Int Ed 54:11740–11744CrossRefGoogle Scholar
  69. 69.
    Yamada Y, Yamamoto T, Okawara M (1975) Chem Lett 361–362Google Scholar
  70. 70.
    Breslow R, Gellman SH (1982) J Chem Soc Chem Commun 1400–1401Google Scholar
  71. 71.
    Breslow R, Gellman SH (1983) J Am Chem Soc 105:6728–6729CrossRefGoogle Scholar
  72. 72.
    Mansuy D, Mahy JP, Dureault A, Bedi G, Battioni P (1984) J Chem Soc Chem Commun 1161–1163Google Scholar
  73. 73.
    Evans DA, Faul MM, Bilodeau MT (1991) J Org Chem 56:6744–6746CrossRefGoogle Scholar
  74. 74.
    Evans DA, Bilodeau MT, Faul MM (1994) J Am Chem Soc 116:2742–2753CrossRefGoogle Scholar
  75. 75.
    Chang JWW, Ton TMU, Chan PWH (2011) Chem Rec 11:331–357CrossRefGoogle Scholar
  76. 76.
    Karila D, Dodd RH (2011) Curr Org Chem 15:1507–1538CrossRefGoogle Scholar
  77. 77.
    Dequirez G, Pons V, Dauban P (2012) Angew Chem Int Ed 51:7384–7395CrossRefGoogle Scholar
  78. 78.
    Du Bois J (2011) Org Process Res Dev 15:758–762CrossRefGoogle Scholar
  79. 79.
    Roizen JL, Harvey ME, Du Bois J (2012) Acc Chem Res 45:911–922CrossRefGoogle Scholar
  80. 80.
    Zhou X-G, Yu X-Q, Huang J-S, Che C-M (1999) Chem Commun 2377–2378Google Scholar
  81. 81.
    Brandt P, Södergren MJ, Andersson PG, Norrby P-O (2000) J Am Chem Soc 122:8013–8020CrossRefGoogle Scholar
  82. 82.
    Zdilla MJ, Abu-Omar MM (2006) J Am Chem Soc 128:16971–16979CrossRefGoogle Scholar
  83. 83.
    Zdilla MJ, Abu-Omar MM (2008) Inorg Chem 47:10718–10722Google Scholar
  84. 84.
    Lin X, Zhao C, Che C-M, Ke Z, Phillips DL (2007) Chem Asian J 2:1101–1108CrossRefGoogle Scholar
  85. 85.
    Lin X, Che C-M, Phillips DL (2008) J Org Chem 73:529–537CrossRefGoogle Scholar
  86. 86.
    Han H, Park SB, Kim SK, Chang S (2008) J Org Chem 73:2862–2870CrossRefGoogle Scholar
  87. 87.
    Ke Z, Cundari TR (2010) Organometallics 29:821–834CrossRefGoogle Scholar
  88. 88.
    Perry RH, Cahill TJ III, Roizen JL, Du Bois J, Zare RN (2012) Proc Natl Acad Sci U S A 109:18295–18299CrossRefGoogle Scholar
  89. 89.
    Fiori KW, Espino CG, Brodsky BH, Du Bois J (2009) Tetrahedron 65:3042–3051CrossRefGoogle Scholar
  90. 90.
    Goure E, Avenier F, Dubourdeaux P, Seneque O, Albrieux F, Lebrun C, Clemancey M, Maldivi P, Latour J-M (2014) Angew Chem Int Ed 53:1580–1584CrossRefGoogle Scholar
  91. 91.
    Dohi T, Kita Y (2009) Chem Commun 2073–2085Google Scholar

Copyright information

© Springer International Publishing Switzerland 2015

Authors and Affiliations

  1. 1.Department of ChemistryCase Western Reserve UniversityClevelandUSA

Personalised recommendations