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Catalytic Hydroamination of Unsaturated Hydrocarbons

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Abstract

The review summarizes the state of the art in the field of hydroamination of diverse unsaturated hydrocarbons, including activated and non-activated acetylenes, dienes, alkenes. The catalytic systems reviewed include mostly heterogeneous nano-engineered materials, while homogeneous catalysts are presented for comparative purposes.

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References

  1. Beller M, Breindl C (1998) Tetrahedron 54:6359–6368

    Article  CAS  Google Scholar 

  2. Widenhoefer RA, Han X (2006) Eur J Org Chem 20:4555–4563

    Article  CAS  Google Scholar 

  3. Penzien J, Su RQ, Muller TE (2002) J Mol Catal 182–183:489–498

    Article  Google Scholar 

  4. Tanabe K, Holderlich WF (1999) Appl Catal A 181:399

    Article  CAS  Google Scholar 

  5. Houben-Weyl Methoden der Organischen Chemie, Georg Thieme Verlag, Stuttgart, 1957, Fourth Edition XI/I, 1

  6. Hartung C, Breindl C, Tillack A, Beller M (2000) Tetrahedron 56:5157–5162

    Article  CAS  Google Scholar 

  7. Lapis AAM, DaSilveira BA, Scholten JD, Nachtigall FM, Eberlin MN, Dupont J (2006) Tetrahedron Lett 47:6775–6779

    Article  CAS  Google Scholar 

  8. Müller TE, Hultzsch KC, Yus M, Foubelo F, Tada M (2008) Chem Rev 108:3795–3892

    Article  CAS  Google Scholar 

  9. Hummel S, Kirsch SF (2011) Beilstein J Org Chem 7:847–859

    Article  CAS  Google Scholar 

  10. Ciobanu M, Tirsoaga A, Amoros P, Beltran D, Coman SM, Parvulescu VI (2014) Appl Catal A 474:230–235

    Article  CAS  Google Scholar 

  11. Hong S, Marks TJ (2004) Acc Chem Res 37:673–686

    Article  CAS  Google Scholar 

  12. Roesky W, Müller TEM (2003) Angew Chem Int Ed 42:2708–2710

    Article  CAS  Google Scholar 

  13. Maurya MR, Arya A, Kumar U, Kumar A, Avecilla F, Pessoa JC (2009) Dalton Trans 43:9555–9566

    Article  CAS  Google Scholar 

  14. Beller M, Breindl C, Eichberger M, Hartung CG, Seayad J, Thiel OR, Tillack A, Trauthwein H (2002) Synlett 10:1579–1594

    Article  Google Scholar 

  15. Müller TE, Beller M (1998) Chem Rev 98:675–703

    Article  Google Scholar 

  16. Steinborn D, Taube R (1986) Z Chem 26:349–359

    Article  CAS  Google Scholar 

  17. Beller M, Seayad J, Tillack A, Jiao H (2004) Angew Chem 43:3368–3398

    Article  CAS  Google Scholar 

  18. Pohlki F, Doye S (2003) Chem Soc Rev 32:104–114

    Article  CAS  Google Scholar 

  19. Shi Y, Ciszewski T, Odom AL (2001) Organometallics 20:3967–3969

    Article  CAS  Google Scholar 

  20. Ryu JS, Marks GTJ (2003) J Am Chem Soc 125:12584–12605

    Article  CAS  Google Scholar 

  21. Hermanns N, Dahmen S, Bolm C, Bräse S (2002) Angew Chem Int Ed 41:3692–3694

    Article  CAS  Google Scholar 

  22. Gasc MB, Lattes A, Perie JJ (1983) Tetrahedron 39:703–731

    Article  CAS  Google Scholar 

  23. Zhang J, Yang CG, He C (2006) J Am Chem Soc 128:1798–1799

    Article  CAS  Google Scholar 

  24. Kitahara H, Kamiya I, Sakurai H (2009) Chem Lett 38(9):908–909

    Article  CAS  Google Scholar 

  25. Marcsekova K, Doye S (2007) Synthesis 1:145–154

    Google Scholar 

  26. Yang L, Xu LW, **a CG (2009) Synthesis 12:1969–1974

    Google Scholar 

  27. Lehmkuhl H, Reinehr D (1973) J Organomet Chem 55:215–220

    Article  CAS  Google Scholar 

  28. Pez GP, Galle GE (1985) Pure Appl Chem 57:1917–1926

    Article  CAS  Google Scholar 

  29. Steinborn D, Thies B, Wagner I, Taube R (1989) Z Chem 29:333–334

    Article  CAS  Google Scholar 

  30. Brouwer C, He C (2006) Angew Chem Int Ed 45:1744–1747

    Article  CAS  Google Scholar 

  31. Han XQ, Widenhoefer RA (2006) Angew Chem Int Ed 45:1747–1749

    Article  CAS  Google Scholar 

  32. Stubbert BD, Stern CL, Marks TJ (2003) Organometallics 22:4836–4838

    Article  CAS  Google Scholar 

  33. Giardello MA, Conticello VP, Brard L, Gagne MR, Marks TJ (1994) J Am Chem Soc 116:10241–102546

    Article  CAS  Google Scholar 

  34. Anderson LL, Arnold J, Bergman RG (2005) J Am Chem Soc 127:14542–14543

    Article  CAS  Google Scholar 

  35. Qian H, Widenhoefer RA (2005) Org Lett 7:2635–2638

    Article  CAS  Google Scholar 

  36. Taylor JG, Whittall N, Hii KK (2006) Org Lett 8:3561–3564

    Article  CAS  Google Scholar 

  37. Michaux J, Terrasson V, Marque S, Wehbe J, Prim D, Campagne JM (2007) Eur J Org Chem 16:2601–2603

    Article  CAS  Google Scholar 

  38. Huang JM, Wong CM, Xu FX, Loh TP (2007) Tetrahedron Lett 48:3375–3377

    Article  CAS  Google Scholar 

  39. Dion I, Beauchemin AM (2011) Angew Chem Int Ed 50:8233–8235

    Article  CAS  Google Scholar 

  40. Müller TE, Lercher JA, Nhu NV (2003) AIChE J 49:214–224

    Article  Google Scholar 

  41. Li H, Wang C, Huang H, Xu X, Li Y (2011) Tetrahedron Lett 52:1108–1111

    Article  CAS  Google Scholar 

  42. Werkmeister S, Fleischer S, Zhou S, Junge K, Beller M (2012) ChemSusChem 5:777–782

    Article  CAS  Google Scholar 

  43. Brunet JJ, Chu NC, Diallo O (2005) Organometallics 24:3104–3110

    Article  CAS  Google Scholar 

  44. Ackermann L, Bergman RG (2002) Org Lett 4:1475–1478

    Article  CAS  Google Scholar 

  45. Müller TE (1998) Tetrahedron Lett 39:5961–59628

    Article  Google Scholar 

  46. Brinkmann C, Barrett AGM, Hill MS, Procopiou PA (2012) J Am Chem Soc 134:2193–2207

    Article  CAS  Google Scholar 

  47. Seayad J, Tillack A, Hartung CG, Beller M (2002) Adv Synth Catal 344:795–813

    Article  CAS  Google Scholar 

  48. Michaux J, Terrasson V, Marque S, Wehbe J, Prim D, Campagne JM (2007) Eur J Org Chem 16:2601–2603

    Article  CAS  Google Scholar 

  49. Tada M, Shimamoto M, Sasaki T, Iwasawa Y (2004) Chem Commun 22:2562–2563

    Article  CAS  Google Scholar 

  50. Sudheesh N, Shukla RS (2013) Appl Catalysis A 453:159–166

    Article  CAS  Google Scholar 

  51. Maurya MR, Pessoa JC (2011) J Organomet Chem 696(1):244–254

    Article  CAS  Google Scholar 

  52. Sievers C, Jiménez O, Knapp R, Lin X, Müller TE, Türler A, Wierczinski B, Lercher JA (2008) J Molec Catal A 279:187–199

    Article  CAS  Google Scholar 

  53. Sievers C, Jimenez O, Müller TE, Steuernagel S, Lercher JA (2006) J Am Chem Soc 128:13990–13991

    Article  CAS  Google Scholar 

  54. Jimenez O, Muller TE, Sievers C, Spirkl A, Lercher JA (2006) Chem Commun 28:2974–2976

    Article  Google Scholar 

  55. Ng EP, Law SP, Mukti RR, Juan JC, Adam F (2014) Chem Eng J 243:99–107

    Article  CAS  Google Scholar 

  56. Yang L, Xu LW, **a CG (2008) Tetrahedron Lett 49(18):2882–2885

    Article  CAS  Google Scholar 

  57. Lingaiah N, Babu NS, Reddy KM, Prasad PSS, Suryanarayana I (2007) Chem Commun 3:278–279

    Article  Google Scholar 

  58. Penzien J, Haeßner C, Jentys A, Köhler K, Müller TE, Sievers C, Lercher JA (2004) J Catal 221:302–312

    Article  CAS  Google Scholar 

  59. Shanbhag GV, Kumbar SM, Joseph T, Halligudi SB (2006) Tetrahedron Lett 47:141–143

    Article  CAS  Google Scholar 

  60. Joseph T, Shanbhag GV, Halligudi SB (2005) J Mol Catal A 236(1–2):139–144

    Article  CAS  Google Scholar 

  61. Shanbhag GV, Halligudi SB (2004) J Mol Catal A 222(1–2):223–228

    Article  CAS  Google Scholar 

  62. Joseph T, Shanbhag GV, Sawant DP, Halligudi SB (2006) J Mol Catal A 250(1–2):210–217

    Article  CAS  Google Scholar 

  63. Shanbhag GV, Joseph T, Halligudi SB (2007) J Catal 250(2):274–282

    Article  CAS  Google Scholar 

  64. Shanbhag GV, Kumbar SM, Halligudi SB (2008) J Mol Catal A 284(1–2):16–23

    Article  CAS  Google Scholar 

  65. Komura K, Tsutsui J, Hongo R, Sugi Y (2007) Stud Surf Sci Catal 170:1111–1119

    Article  Google Scholar 

  66. Penzien J, Su RQ, Müller TE (2002) J Mol Catal A 182–183:489–498

    Article  Google Scholar 

  67. Penzien J, Abraham A, van Bokhoven JA, Jentys A, Müller TE, Sievers C, Lercher JA (2004) J Phys Chem B 108(13):4116–4126

    Article  CAS  Google Scholar 

  68. Breitenlechner S, Fleck M, Müller TE, Suppan A (2004) J Mol Catal A 214:175–179

    Article  CAS  Google Scholar 

  69. Jiménez O, Müller TE, Schwieger W, Lercher JA (2004) Stud Surf Sci Catal 154(C):2788–2794

    Article  Google Scholar 

  70. Jimenez O, Müller TE, Schwieger W, Lercher JA (2006) J Catal 239(1):42–50

    Article  CAS  Google Scholar 

  71. Penzien J, Müller TE, Lercher JA (2001) Micropor Mesopor Mater 48(1–3):285–291

    Article  CAS  Google Scholar 

  72. Kore R, Satpati B, Srivastava R (2014) Appl Catal A 477:8–17

    Article  CAS  Google Scholar 

  73. Corma A, Concepción P, Domínguez I, Fornés V, Sabater MJ (2007) J Catal 251:39–47

    Article  CAS  Google Scholar 

  74. Yin MY, Yuan GL, Wu YQ, Huang MY, Jiang YY (1999) J Molec Catal A 147:93–98

    Article  CAS  Google Scholar 

  75. Bhanushali MJ, Nandurkar NS, Bhor MD, Bhanage BM (2008) Catal Commun 9(3):425–430

    Article  CAS  Google Scholar 

  76. Liu PN, **a F, Zhao ZL, Wang QW, Ren YJ (2011) Tetrahedron Lett 52(46):6113–6117

    Article  CAS  Google Scholar 

  77. Zhang S, Wei Y, Yin S, Au CT (2011) Catal Commun 12(8):712–716

    Article  CAS  Google Scholar 

  78. Pârvulescu VI, Hardacre C (2007) Chem Rev 107:2615–2665

    Article  CAS  Google Scholar 

  79. Kitahara H, Sakurai H (2010) Chem Lett 39:46–48

    Article  CAS  Google Scholar 

  80. Kitahara H, Sakurai H (2011) J Organomet Chem 696:442–449

    Article  CAS  Google Scholar 

  81. Scheeren CW, Machado G, Teixeira SR, Morais J, Domingos JB, Dupont J (2006) J Phys Chem B 110:13011–13020

    Article  CAS  Google Scholar 

  82. Li Z, Jia Z, Luan Y, Mu T (2009) Curr Opin Solid State Mater Sci 12:1–8

    Article  CAS  Google Scholar 

  83. Ruta M, Laurenczy G, Dyson PJ, Kiwi-Minsker L (2008) J Phys Chem C 112:17814–17819

    Article  CAS  Google Scholar 

  84. de Caro D, Jacob K, Faulmann C, Legros JP, Senocq F, Fraxedas J, Valade L (2010) Synth Met 160:1223–1227

    Article  CAS  Google Scholar 

  85. Hu Y, Yang H, Zhang Y, Hou Z, Wang X, Qiao Y, Li H, Feng B, Huang Q (2009) Catal Commun 10:1903–1907

    Article  CAS  Google Scholar 

  86. Dupont J, Fonseca GS, Umpierre AP, Fichtner PFP, Teixeira SR (2002) J Am Chem Soc 124:4228–4229

    Article  CAS  Google Scholar 

  87. Fonseca GS, Umpierre AP, Fichtner PFP, Teixeira SR, Dupont J (2003) Chem Eur J 9:3263–3269

    Article  CAS  Google Scholar 

  88. Mikkola JP, Virtanen PP, Kordás K, Karhu H, Salmi T (2007) Appl Catal A 328:68–76

    Article  CAS  Google Scholar 

  89. Dash P, Dehm NA, Scott RWJ (2008) J Mol Catal A 286:114–119

    Article  CAS  Google Scholar 

  90. Coman SM, Florea M, Parvulescu VI, David V, Medvedovici A, De Vos D, Jacobs PA, Poncelet G, Grange P (2007) J Catal 249:359–369

    Article  CAS  Google Scholar 

  91. Kume Y, Qiao K, Tomida D, Yokoyama C (2008) Catal Commun 9:369–375

    Article  CAS  Google Scholar 

  92. Eddaoudi M, Kim J, Rosi NL, Vodak D, Wachter J, O’Keefi M, Yaghi OM (2002) Science 295:469–473

    Article  CAS  Google Scholar 

  93. Oliveira RL, He W, Gebbink RJMK, de Jong KP (2015) Catal Sci Technol 5:1919–1928

    Article  CAS  Google Scholar 

  94. Hao Y, Chong Y, Li S, Yang H (2012) J Phys Chem C 116:6512–6519

    Article  CAS  Google Scholar 

  95. Li JR, Kupple RJ (2009) Chem Soc Rev 38:1477–1504

    Article  CAS  Google Scholar 

  96. Farrusseng D, Aguado S, Pinel C (2009) Angew Chem Int Ed 48:7502–7513

    Article  CAS  Google Scholar 

  97. Pintado-Sierra M, Rasero-Almansa AM, Corma A, Iglesias M, Sánchez F (2013) J Catal 299:137–145

    Article  CAS  Google Scholar 

  98. Peeters A, Valvekens P, Vermoortele F, Ameloot R, Kirschhock C, De Vos D (2011) Chem Commun 47(14):4114–4116

    Article  CAS  Google Scholar 

  99. Corma A, Garcia H (2008) Chem Soc Rev 37:2096–2126

    Article  CAS  Google Scholar 

  100. Giljohann DA, Seferos DS, Daniel WL, Massich MD, Patel PC, Mirkin CA (2010) Angew Chem Int Ed 49:3280–3294

    Article  CAS  Google Scholar 

  101. Haruta M (1997) Catal Today 36:153–166

    Article  CAS  Google Scholar 

  102. Hashmi ASK, Hutchings GJ (2006) Angew Chem Int Ed 45:7896–7936

    Article  Google Scholar 

  103. Haruta M (2003) Chem Rec 3:75–87

    Article  CAS  Google Scholar 

  104. Huang H, Zhou Y, Liu H (2011) Beilstein J Org Chem 7:897–936

    Article  CAS  Google Scholar 

  105. Nun P, Dupuy S, Gaillard S, Poater A, Caravallo L, Nolan SP (2011) Catal Sci Technol 1:56–61

    Article  CAS  Google Scholar 

  106. Ito H, Harada T, Ohmiya H, Sawamura M (2011) Beilstein J Org Chem 7:951–959

    Article  CAS  Google Scholar 

  107. Seral-Ascaso A, Luquin A, Lázaro MJ, de la Fuentec GF, Laguna M, Muñoz E (2013) Appl Catal A 456:88–95

    Article  CAS  Google Scholar 

  108. Kimling J, Maier M, Okenve M, Kotaidis V, Ballot H, Plech A (2006) J Phys Chem B 110:15700–15707

    Article  CAS  Google Scholar 

  109. Sivaraman SK, Kumar S, Santhanam V (2011) Colloid Interface Sci 361:543–547

    Article  CAS  Google Scholar 

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Acknowledgments

The work was carried out with a financial support from the Russian Science Foundation, project No. 14-50-00126.

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Correspondence to Leonid M. Kustov.

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Isaeva, V.I., Kustov, L.M. Catalytic Hydroamination of Unsaturated Hydrocarbons. Top Catal 59, 1196–1206 (2016). https://doi.org/10.1007/s11244-016-0640-9

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