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Gold-Catalyzed Synthesis of Nitrogen Heterocyclic Compounds via Hydroamination Reactions

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Au-Catalyzed Synthesis and Functionalization of Heterocycles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 46))

Abstract

Gold catalysis is a very attractive tool for the synthesis of nitrogen heterocyclic compounds by means of hydroamination reactions. This chapter intends to present selected examples of more recent developments in this field which highlight relevant progresses in terms of control of the chemo-, regio-, and stereoselectivity of hydroamination processes in their applications to the synthesis of the corresponding heterocyclic derivatives by means of gold catalysis.

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References

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

    Article  CAS  Google Scholar 

  2. Müller TE, Beller M (1998) Chem Rev 98:675

    Article  Google Scholar 

  3. Huang L, Arndt M, Gooβen K, Heydt H, Gooβen LJ (2015) Chem Rev 115:2596

    Article  CAS  Google Scholar 

  4. Bernoud E, Lepori C, Mellah M, Schulz E, Hannedouche J (2015) Catal Sci Technol 5:2017

    Article  CAS  Google Scholar 

  5. Patil NT, Kavthe RD, Shinde VS (2012) Tetrahedron 68:8079

    Article  CAS  Google Scholar 

  6. Yadav JS, Antony A, Rao TS, Subba Reddy BV (2011) J Organomet Chem 696:16

    Article  CAS  Google Scholar 

  7. Severin R, Doye S (2007) Chem Soc Rev 36:1407

    Article  CAS  Google Scholar 

  8. Alonso F, Beletskaya IP, Yus M (2004) Chem Rev 104:3079

    Article  CAS  Google Scholar 

  9. Ohno H, Chiba H, Inuki S, Oishi S, Fujii N (2014) Synlett 25:179

    Article  CAS  Google Scholar 

  10. Krause N, Winter C (2011) Chem Rev 111:1994

    Article  CAS  Google Scholar 

  11. Zeng X (2013) Chem Rev 113:6864

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  13. Hashmi ASK, Bührle M (2010) Aldrichimica Acta 43:27

    CAS  Google Scholar 

  14. Widenhoefer R, Han X (2006) Eur J Org Chem 4555

    Google Scholar 

  15. Toste FD, Michelet V (eds) (2014) Gold catalysis: an homogeneous approach. Imperial College Press, London

    Google Scholar 

  16. Ranieri B, Escofet I, Echavarren AM (2015) Org Biomol Chem 13:7103

    Article  CAS  Google Scholar 

  17. Jia M, Bandini M (2015) ACS Catal 5:1638

    Article  CAS  Google Scholar 

  18. Hashmi ASK, Toste FD (2012) Modern gold catalyzed synthesis. Wiley, Weinheim

    Book  Google Scholar 

  19. Lo VK-R, Chan AO-Y, Che C-M (2015) Org Biomol Chem 13:6667

    Article  CAS  Google Scholar 

  20. Bour C, Gandon V (2015) Synlett 26:1427

    Article  CAS  Google Scholar 

  21. Fürstner L (2014) Acc Chem Res 47:925

    Article  CAS  Google Scholar 

  22. Zhang D, Tang X-Y, Shi M (2014) Acc Chem Res 47:913

    Article  CAS  Google Scholar 

  23. Abbiati G, Rossi E (2014) Beistein J Org Chem 10:481

    Article  CAS  Google Scholar 

  24. Liu X, He L, Liu Y-M, Cao Y (2014) Acc Chem Res 47:793

    Article  CAS  Google Scholar 

  25. Fensterbank L, Malacria M (2014) Acc Chem Res 47:9

    Article  CAS  Google Scholar 

  26. Rudolph M, Hashmi ASK (2012) Chem Soc Rev 41:24

    Article  Google Scholar 

  27. Lu B-L, Dai L, Shi M (2012) Chem Soc Rev 41:3318

    Article  CAS  Google Scholar 

  28. Brenzovich WE Jr (2012) Angew Chem Int Ed 51:8933

    Article  CAS  Google Scholar 

  29. Liu L-P, Hammond GB (2012) Chem Soc Rev 41:3129

    Article  CAS  Google Scholar 

  30. Corma A, Leyva-Pérez A, Sabater MJ (2011) Chem Rev 111:1657

    Article  CAS  Google Scholar 

  31. Hashmi ASK (2010) Angew Chem Int Ed 49:5232

    Article  CAS  Google Scholar 

  32. Shapiro ND, Toste FD (2010) Synlett 675

    Google Scholar 

  33. Abu Sohel SM, Liu R-S (2009) Chem Soc Rev 38:2269

    Article  CAS  Google Scholar 

  34. Nevado C (2010) Chimia 64:247

    Article  CAS  Google Scholar 

  35. Fürstner A (2009) Chem Soc Rev 38:3208

    Article  CAS  Google Scholar 

  36. Arcadi A (2008) Chem Rev 108:3266

    Article  CAS  Google Scholar 

  37. Li Z, Brouwer C, He C (2008) Chem Rev 108:3239

    Article  CAS  Google Scholar 

  38. Skouta R, Li C-J (2008) Tetrahedron 64:4917

    Article  CAS  Google Scholar 

  39. Hashmi ASK, Rudolph M (2008) Chem Soc Rev 37:1766

    Article  CAS  Google Scholar 

  40. Muzart J (2008) Tetrahedron 64:5815

    Article  CAS  Google Scholar 

  41. Gorin DJ, Sherry BD, Toste FD (2008) Chem Rev 108:3351

    Article  CAS  Google Scholar 

  42. Hashmi ASK (2007) Chem Rev 107:3180

    Article  CAS  Google Scholar 

  43. Shen HC, Graham TM (2013) Drug Discov Today Technol 10, e3

    Article  Google Scholar 

  44. Rudolf M, Hashmi ASK (2011) Chem Commun 47:6536

    Article  CAS  Google Scholar 

  45. Das A, Abu Sohel SM, Liu R-S (2010) Org Biomol Chem 8:860

    Article  CAS  Google Scholar 

  46. Shen HC (2008) Tetrahedron 64:7847

    Article  CAS  Google Scholar 

  47. Patil NT, Yamamoto Y (2008) Chem Rev 108:3395

    Article  CAS  Google Scholar 

  48. Shen HC (2008) Tetrahedron 64:3885

    Article  CAS  Google Scholar 

  49. Fukuda Y, Utimoto K (1991) Synthesis 975

    Google Scholar 

  50. Fukuda Y, Utimoto K, Nozaki H (1987) Heterocycles 25:297

    Article  CAS  Google Scholar 

  51. Patil NT, Singh V (2011) J Organomet Chem 696:419

    Article  CAS  Google Scholar 

  52. Minkler SRK, Isley NA, Lippincott DJ, Krause N (2014) Org Lett 16:724

    Article  CAS  Google Scholar 

  53. Ritzen B, Richelle GJJ, Brocken L, van Delft FL, Rutjes FPJT (2014) Synlett 25:270

    CAS  Google Scholar 

  54. Yu Y-F, Shu C, Zhou B, Li J-Q, Zhou J-M, Ye L-W (2015) Chem Commun 51:2126

    Article  CAS  Google Scholar 

  55. Zeng Q, Zhang L, Yang J, Xu B, Xiao Y, Zhang J (2014) Chem Commun 50:4205

    Google Scholar 

  56. Yoshimanu M, Ohta K, Takahashi N (2012) Chem Eur J 18:15602

    Article  CAS  Google Scholar 

  57. Barbour PM, Marholz LL, Chang L, Xu W, Wang X (2014) Chem Lett 43:572

    Article  CAS  Google Scholar 

  58. Abbiati G, Marinelli F, Rossi E, Arcadi A (2013) Isr J Chem 53:856

    Article  CAS  Google Scholar 

  59. Zhdanko A, Maier ME (2014) Angew Chem Int Ed 53:7760

    Article  CAS  Google Scholar 

  60. Hashmi ASK, Ramamurthi TD, Rominger F (2010) Adv Synth Catal 352:971

    Article  CAS  Google Scholar 

  61. Gala E, Córdoba M, Izquierdo ML, Álvarez-Builla J (2014) Arkivoc (V):319

    Google Scholar 

  62. Gaggioli CA, Ciancaleoni G, Biasiolo L, Bistoni G, Zuccaccia D, Belpassi D, Belazoni P, Tarantelli F (2015) Chem Commun 51:5990

    Article  CAS  Google Scholar 

  63. Zeng X, Kinjo R, Donnadieu B, Bertrand G (2010) Angew Chem Int Ed 45:942

    Article  CAS  Google Scholar 

  64. Morozov OS, Lunchev AV, Bush AA, Tukov AA, Asachenko AF, Khrustalev VN, Zalesskiy SS, Ananikov VP, Nechaev MS (2014) Chem Eur J 20:6162

    Article  CAS  Google Scholar 

  65. Hashmi ASK (2014) Acc Chem Res 47:864

    Article  CAS  Google Scholar 

  66. Obradors C, Echavarren AM (2014) Chem Commun 50:16

    Article  CAS  Google Scholar 

  67. Weber D, Gagne MR (2013) Chem Sci 4:335

    Article  CAS  Google Scholar 

  68. Braun I, Asiri AM, Hashmi ASK (2013) ACS Catal 3:1902

    Article  CAS  Google Scholar 

  69. Cheong PH-Y, Morganelli P, Luzung MR, Houk KN, Toste FD (2008) J Am Chem Soc 130:4517

    Article  CAS  Google Scholar 

  70. Gimeno A, Cuenca AB, Suárez-Pantiga S, de Arellano RC, Medio-Simón M, Asensio G (2014) Chem Eur J 20:683

    Article  CAS  Google Scholar 

  71. Ciano L, Fey N, Halliday CJV, Lyman JM, Milner LM, Mistry N, Pridmore NE, Townsend NS, Whitwood AC (2015) Chem Commun 51:9702

    Article  CAS  Google Scholar 

  72. Jiang Y, Tang X-Y, Shi M (2015) Chem Eur J 21:7675

    Article  CAS  Google Scholar 

  73. Belger K, Krause N (2015) Org Biomol Chem 13:8556

    Article  CAS  Google Scholar 

  74. Li S, Li Z, Yuan Y, Peng D, Li Y, Zhang L, Wu Y (2012) Org Lett 14:1130

    Article  CAS  Google Scholar 

  75. Bouvet S, Moreau X, Coeffard V, Greck C (2012) J Org Chem 78:427

    Article  CAS  Google Scholar 

  76. Pereshivko OP, Peshkov AV, Peshkov AA, Jacobs J, Van Meervelt L, Van der Eychen EV (2014) Org Biomol Chem 12:1741

    Article  CAS  Google Scholar 

  77. Pereshivko OP, Peshkov AV, Jacobs J, Van Meervelt L, Van der Eychen EV (2013) Adv Synth Catal 355:781

    Article  CAS  Google Scholar 

  78. Peshkov AV, Pereshivko OP, Sharma S, Meganathan T, Parmar VS, Ermolat'ev DS, Van der Eychen EV (2011) J Org Chem 76:5867

    Article  CAS  Google Scholar 

  79. Gupta S, Koley D, Ravikumar K, Kundu B (2013) J Org Chem 78:8624

    Article  CAS  Google Scholar 

  80. Danda A, Kumar K, Waldmann H (2015) Chem Commun 51:7536

    Article  CAS  Google Scholar 

  81. Jha RR, Saunthwal RK, Verma AK (2014) Org Biomol Chem 12:522

    Article  Google Scholar 

  82. Seppänen O, Muuronen M, Helaja J (2014) Eur J Org Chem 4044

    Google Scholar 

  83. Schröder F, Ojeda M, Erdmann N, Jacobs J, Luque R, Noël T, Van Meervelt L, Van der Eychen J, Van der Eychen EV (2015) Green Chem 17:3314

    Article  CAS  Google Scholar 

  84. Yao L-F, Wang Y, Huang K-W (2015) Org Chem Front 2:721

    Article  CAS  Google Scholar 

  85. James T, Simpson I, Grant JA, Sridhran V, Nelson A (2013) Org Lett 15:6094

    Article  CAS  Google Scholar 

  86. Basceken S, Balci M (2015) J Org Chem 80:3806

    Article  CAS  Google Scholar 

  87. Morita N, Krause N (2004) Org Lett 6:4121

    Article  CAS  Google Scholar 

  88. Nishina N, Yamamoto Y (2006) Angew Chem Int Ed 45:3314

    Article  CAS  Google Scholar 

  89. Zhang Z, Liu C, Kinder RE, Han X, Qian H, Widenhoefer RA (2006) J Am Chem Soc 128:9066

    Article  CAS  Google Scholar 

  90. Yu S, Ma S (2012) Angew Chem Int Ed 51:3074

    Article  CAS  Google Scholar 

  91. Alcaide B, Almendros P (2011) Adv Synth Catal 353:2561

    Article  CAS  Google Scholar 

  92. Bates RW, Satcharoen V (2002) Chem Soc Rev 31:12

    Article  CAS  Google Scholar 

  93. Yang W, Hashmi ASK (2014) Chem Soc Rev 43:2941

    Article  CAS  Google Scholar 

  94. Winter C, Krause N (2009) Angew Chem Int Ed 48:6339

    Article  CAS  Google Scholar 

  95. Li H, Widenhoefer RA (2009) Org Lett 11:2671

    Article  CAS  Google Scholar 

  96. Bates RW, Dewey MR (2009) Org Lett 11:3706

    Article  CAS  Google Scholar 

  97. LaLonde RL, Sherry BD, Kang EJ, Toste FD (2007) J Am Chem Soc 129:2452

    Article  CAS  Google Scholar 

  98. Wang Y-M, Lackner AD, Toste AF (2014) Acc Chem Res 47:889

    Article  CAS  Google Scholar 

  99. Nguyen BN, Adrio LA, Barreiro EM, Brazier JB, Haycock P, Hii KK, Nachtegaal M, Newton MA, Szlachetko J (2012) Organometallics 31:2395

    Article  CAS  Google Scholar 

  100. Aikawa K, Kojima M, Mikami K (2009) J Am Chem Soc 48:6073

    CAS  Google Scholar 

  101. LaLonde RL, Wang ZJ, Mba M, Lackner AD, Toste FD (2010) Angew Chem Int Ed 49:598

    Article  CAS  Google Scholar 

  102. Zhang Z, Bender CF, Widenhoefer RA (2007) Org Lett 9:1935

    Article  CAS  Google Scholar 

  103. Teller H, Corbet M, Mantilli L, Gopakumar G, Goddard R, Thiel W, Fürstner A (2012) J Am Chem Soc 134:15331

    Article  CAS  Google Scholar 

  104. Roth T, Wadepohl H, Wright DS, Gade LH (2013) Chem Eur J 19:12823

    Article  CAS  Google Scholar 

  105. Rodríguez L-I, Roth T, Fillol JL, Wadepol H, Gade LH (2012) Chem Eur J 18:3721

    Article  CAS  Google Scholar 

  106. Wang Z, Zheng H, Yang J, Xie X, She X (2015) Adv Synth Catal 357:2082

    Article  CAS  Google Scholar 

  107. Broggini G, Borsini E, Fasana A, Poli G, Liron F (2012) Eur J Org Chem 3617

    Google Scholar 

  108. Higginbotham MCM, Kennedy L, Lindsay AG, Troester A, Bebbington MWP (2015) Tetrahedron 71:727

    Article  CAS  Google Scholar 

  109. Bebbington MWP, Higginbotham MCM (2012) Chem Commun 48:7565

    Article  CAS  Google Scholar 

  110. Pflästerer D, Dolbundalchok P, Rafique S, Rudolph M, Rominger F, Hashmi ASK (2013) Adv Synth Catal 355:1383

    Article  CAS  Google Scholar 

  111. Bermoud E, Lepori M, Mellah M, Schulz E, Hannedouce J (2015) Catal Sci Technol 5:2017

    Article  CAS  Google Scholar 

  112. Chiarucci M, Bandini M (2013) Beilstein J Org Chem 2586

    Google Scholar 

  113. Zhang J, Yang C-G, He C (2006) J Am Chem Soc 128:1798

    Article  CAS  Google Scholar 

  114. Liu X-Y, Li C-H, Che C-M (2006) Org Lett 8:2707

    Article  CAS  Google Scholar 

  115. Kitahara H, Sakurai H (2011) J Organomet Chem 696:442

    Article  CAS  Google Scholar 

  116. Bender CF, Widenhoefer RA (2006) Chem Commun 4143

    Google Scholar 

  117. Bender CF, Widenhoefer RA (2006) Org Lett 8:5303

    Article  CAS  Google Scholar 

  118. Seo H, Snead DR, Abboud KA, Hong S (2011) Organometallics 7:2011

    Google Scholar 

  119. LaLonde RL, Brenzovich WE Jr, Benitez D, Tkatchouk E, Kelley K, Goddard WA, Toste FD (2010) Chem Sci 1:226

    Article  CAS  Google Scholar 

  120. Bender CF, Widenhoefer RA (2008) Chem Commun 2741

    Google Scholar 

  121. Kitahara H, Sakurai H (2010) Chem Lett 39:46

    Article  CAS  Google Scholar 

  122. Singh SK, Yadav M, Beherens S, Roesky PW (2013) Dalton Trans 42:10404

    Article  CAS  Google Scholar 

  123. Han J, Shimizu N, Lu Z, Amii H, Hammond GB, Xu B (2014) Org Lett 16:3500

    Article  CAS  Google Scholar 

  124. Kojima M, Mikani K (2012) Synlett 57

    Google Scholar 

  125. Sun Y-W, Xu Q, Shi M (2013) Beilstein J Org Chem 9:2224

    Article  CAS  Google Scholar 

  126. Michon C, Abadie M-A, Medina F, Agbossou-Niedercorn A (2014) Catal Today 235:2

    Article  CAS  Google Scholar 

  127. Abadie M-A, Trivelli X, Medina F, Capet F, Roussel P, Agbossou-Niedercorn F, Michon C (2014) ChemCatChem 6:2235

    Article  CAS  Google Scholar 

  128. Lee SD, Timmerman JC, Widenhoefer RA (2014) Adv Synth Catal 356:3187

    Article  CAS  Google Scholar 

  129. Zhang Z, Lee SD, Widenhoefer RA (2009) J Am Chem Soc 131:5372

    Article  CAS  Google Scholar 

  130. Michelet V (2015) Top Curr Chem 357:95–132

    Article  CAS  Google Scholar 

  131. Quian J, Liu J, Cui J, Xu Z (2012) J Org Chem 77:4484

    Article  CAS  Google Scholar 

  132. Guo P, Zeng X, Chen S, Luo M (2014) J Organomet Chem 751:438

    Article  CAS  Google Scholar 

  133. Alcaide B, Almendros P, Alonso JM, Fernández I, Gómez-Campillos G, Torres MR (2014) Chem Commun 50:4567

    Article  CAS  Google Scholar 

  134. Patil NT, Lakshimi PGVV, Singh V (2010) Eur J Org Chem 4179

    Google Scholar 

  135. Liu G, Zhou Y, Lin D, Wang J, Zhang L, Jiang H, Liu H (2011) ACS Comb Sci 13:209

    Article  CAS  Google Scholar 

  136. Shinde VS, Mane MV, Vanka K, Mallick A, Patil NT (2015) Chem Eur J 21:975

    Article  CAS  Google Scholar 

  137. Han Z-Y, Xiao H, Chen X-H, Gong L-Z (2009) J Am Chem Soc 13:9182

    Article  CAS  Google Scholar 

  138. Du Y-L, Hu Y, Zhu Y-F, Tu X-F, Han Z-Y, Gng L-Z (2015) J Org Chem 80:4754

    Article  CAS  Google Scholar 

  139. Cai S, Yang K, Wang DZ (2014) Org Lett 16:2606

    Article  CAS  Google Scholar 

  140. Ueda H, Yamagushi M, Kameya J, Sugimoto K, Tokuyama H (2014) Org Lett 16:4948

    Article  CAS  Google Scholar 

  141. Zhang S, Ma Y, Lan J, Song F, You J (2015) Org Biomol Chem 13:5867

    Article  CAS  Google Scholar 

  142. Shen C-H, Li L, Zhang W, Liu S, Shu C, Xie Y-E, Fu Y-F (2014) J Org Chem 79:9313

    Article  CAS  Google Scholar 

  143. Tokimizu Y, Oishi S, Fujii N, Ohno H (2015) Angew Chem Int Ed 54:7862

    Article  CAS  Google Scholar 

  144. Wang T, Shi S, Pflästerer D, Rettenmeier E, Rudolph M, Rominger F, Hashmi ASK (2014) Chem Eur J 20:292

    Article  CAS  Google Scholar 

  145. Chiarucci M, Matteucci E, Cera G, Fabrizi G, Bandini M (2013) Chem Asian J 8:1776

    Article  CAS  Google Scholar 

  146. Cera G, Piscitelli S, Chiarucci M, Fabrizi G, Goggiamani A, Ramón RS, Nolan SP, Bandini M (2012) Angew Chem Int Ed 51:9891

    Article  CAS  Google Scholar 

  147. Gimeno A, Rodriguez-Gimeno A, Cuenca AB, de Arellano CM, Medio-Simón M, Asensio G (2015) Chem Commun 51:12384

    Article  CAS  Google Scholar 

  148. Naoe S, Saito T, Uchiyama M, Oishi S, Fujii N, Ohno H (2015) Org Lett 17:1774

    Article  CAS  Google Scholar 

  149. Sharp PP, Banwell MG, Renner J, Lohmann K, Willis AC (2013) Org Lett 15:2616

    Article  CAS  Google Scholar 

  150. Tang H-T, Xiong K, Li R-H, Ding Z-C, Ping Z-P (2015) Org Lett 17:326

    Article  CAS  Google Scholar 

  151. Dhiman S, Ramasastry SSV (2015) Chem Commun 51:557

    Article  CAS  Google Scholar 

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Arcadi, A. (2015). Gold-Catalyzed Synthesis of Nitrogen Heterocyclic Compounds via Hydroamination Reactions. In: Bandini, M. (eds) Au-Catalyzed Synthesis and Functionalization of Heterocycles. Topics in Heterocyclic Chemistry, vol 46. Springer, Cham. https://doi.org/10.1007/7081_2015_5001

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