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Gold-Catalyzed Organic Reactions

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Inventing Reactions

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 44))

Abstract

Although homogeneous gold catalysis was known previously, an exponential growth was only induced 12 years ago. The key findings which induce that rise of the field are discussed. This includes early reactions of allenes and furanynes and intermediates of these conversions as well as hydroarylation reactions. Other substrate types addressed are alkynyl epoxides and N-propargyl carboxamides. Important vinylgold intermediates, the transmetalation from gold to other transition metals, the development of new ligands for gold catalysis, and significant contributions from computational chemistry are other crucial points for the field highlighted here.

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Abbreviations

ICP:

Inductively coupled plasma

IPr:

N,N′-Bis-[2,6-(di-isopropyl)phenyl]imidazol-2-ylidene

KITPHOS:

11-Dicyclohexylphosphino-12-phenyl-9,10-ethenoanthracene

LUMO:

Lowest unoccupied molecular orbital

Me:

Methyl

Mes:

Mesityl

NAC:

Nitrogen-acyclic carbene

NHC:

Nitrogen-heterocyclic carbene

NHOC:

Nitrogen-heterocyclic oxo-carbenes

Ph:

Phenyl

RT:

Room temperature

SE′ :

Electrophilic substitution with rearrangement

Tf:

Trifluoromethylsulfonyl

THT:

Tetrahydrothiophene

References

  1. Schwemberger W, Gordon W (1935) Chem Zentralbl 106:514

    Google Scholar 

  2. Gassman PG, Meyer GR, Williams FJ (1972) J Am Chem Soc 94:7741–7748

    Article  Google Scholar 

  3. Meyer LU, de Meijere A (1976) Tetrahedron Lett 497–500

    Google Scholar 

  4. Gasparrini F, Giovannoli M, Misiti D, Natile G, Palmieri G (1983) Tetrahedron 39:3181–3184

    Article  CAS  Google Scholar 

  5. Ito Y, Sawamura M, Hayashi T (1986) J Am Chem Soc 108:6405–6406

    Article  CAS  Google Scholar 

  6. Togni A, Pastor SD (1990) J Org Chem 55:1649–1664

    Article  CAS  Google Scholar 

  7. Sawamura M, Ito Y (2000) In: Ojima I (ed) Catalytic asymmetric synthesis. Wiley-VCH, Weinheim, pp 493–512

    Google Scholar 

  8. Fukuda Y, Utimoto K, Nozaki H (1987) Heterocycles 25:297–300

    Article  CAS  Google Scholar 

  9. Fukuda Y, Utimoto K (1991) Synthesis 975–978

    Google Scholar 

  10. Fukuda Y, Utimoto K (1991) J Org Chem 56:3729–3731

    Article  CAS  Google Scholar 

  11. Fukuda Y, Utimoto K (1991) Bull Chem Soc Jpn 64:2013–2015

    Article  CAS  Google Scholar 

  12. Teles JH, Schulz M (1997) (BASF AG), WO-A1 9721648 [Chem. Abstr. 127 (1997) 121499]

    Google Scholar 

  13. Teles JH, Brode S, Chabanas M (1998) Angew Chem 110:1475–1478; Angew Chem Int Ed 37:1415–1418

    Google Scholar 

  14. Hashmi ASK, Naumann F, Probst R, Bats JW (1997) Angew Chem 109:127–130; Angew Chem Int Ed Engl 36:104–106

    Google Scholar 

  15. Hashmi ASK, Schwarz L (1997) Chem Ber/Recueil 130:1449–1456

    Article  CAS  Google Scholar 

  16. Hashmi ASK, Naumann F, Bolte M (1998) Organometallics 17:2385–2387

    Article  CAS  Google Scholar 

  17. Hashmi ASK, Rivas Nass A, Bats JW, Bolte M (1999) Angew Chem 111:3565–3567; Angew Chem Int Ed Engl 38:3370–3373

    Google Scholar 

  18. Hashmi ASK (1995) Angew Chem 107:1749–1751; Angew Chem Int Ed Engl 34:1581–1583

    Google Scholar 

  19. Hashmi ASK, Ruppert TL, Knöfel T, Bats JW (1997) J Org Chem 62:7295–7304

    Article  CAS  Google Scholar 

  20. Hashmi ASK, Schwarz L, Bolte M (1998) Tetrahedron Lett 39:8969–8972

    Article  CAS  Google Scholar 

  21. Hashmi ASK, Choi J-H, Bats JW (1999) J Prakt Chem 341:342–357

    Article  CAS  Google Scholar 

  22. Hashmi ASK, Schwarz L, Bats JW (2000) J Prakt Chem 342:40–51

    Article  CAS  Google Scholar 

  23. Hashmi ASK, Schwarz L, Choi J-H, Frost TM (2000) Angew Chem 112:2382–2385; Angew Chem Int Ed 39:2285–2288

    Google Scholar 

  24. Hashmi ASK, Frost TM, Bats JW (2000) J Am Chem Soc 122:11553–11554

    Article  CAS  Google Scholar 

  25. Martín-Matute B, Cardenas CDJ, Echavarren AM (2001) Angew Chem 113:4890–4893; Angew Chem Int Ed 40:4754–4757

    Google Scholar 

  26. Martin-Matute B, Nevado C, Cardenas DJ, Echavarren AM (2001) J Am Chem Soc 125:5757–5766

    Article  Google Scholar 

  27. Hashmi ASK, Wölfle M, Ata F, Hamzic M, Salathé R, Frey W (2006) Adv Synth Catal 348:2501–2508

    Article  CAS  Google Scholar 

  28. Hashmi ASK, Rudolph M, Weyrauch JP, Wölfle M, Frey W, Bats JW (2005) Angew Chem 117:2858–2861; Angew Chem Int Ed 44:2798–2801

    Google Scholar 

  29. Hashmi ASK, Kurpejovic E, Wölfle M, Frey W, Bats JW (2007) Adv Synth Catal 349:1743–1750

    Article  CAS  Google Scholar 

  30. Hashmi ASK, Rudolph M, Siehl H-U, Tanaka M, Bats JW, Frey W (2008) Chem Eur J 14:3703–3708

    Article  CAS  Google Scholar 

  31. Hashmi ASK, Ding L, Bats JW, Fischer P, Frey W (2003) Chem Eur J 9:4339–4345

    Article  CAS  Google Scholar 

  32. Hashmi ASK, Salathé R, Frey W (2006) Chem Eur J 12:6991–6996

    Article  CAS  Google Scholar 

  33. Hashmi ASK, Blanco MC, Kurpejovic E, Frey W, Bats JW (2006) Adv Synth Catal 348:709–713

    Article  CAS  Google Scholar 

  34. Hashmi ASK, Grundl L (2005) Tetrahedron 61:6231–6236

    Article  CAS  Google Scholar 

  35. Hashmi ASK, Häffner T, Rudolph M, Rominger F (2011) Chem Eur J 17:8195–8201

    Article  CAS  Google Scholar 

  36. Hashmi ASK, Hamzic M, Rominger F, Bats JW (2009) Chem Eur J 15:13318–13322

    CAS  Google Scholar 

  37. Hashmi ASK, Hamzic M, Rudolph M, Ackermann M, Rominger F (2009) Adv Synth Catal 351:2469–2481

    Article  CAS  Google Scholar 

  38. Carrettin S, Blanco MC, Corma A, Hashmi ASK (2006) Adv Synth Catal 348:1283–1288

    Article  CAS  Google Scholar 

  39. Hutchings GJ (2007) Catalysis Today 122:196–200

    Article  CAS  Google Scholar 

  40. Toste FD, Gorin DJ, Sherry BD, Toste FD (2008) Chem Rev 108:3351–3378

    Article  Google Scholar 

  41. Chen Y, Yan W, Akhmedov NG, Shi X (2010) Org Lett 12:344–347

    Article  CAS  Google Scholar 

  42. Hashmi ASK, Rudolph M, Huck J, Frey W, Bats JW, Hamzic M (2009) Angew Chem 121:5962–5966; Angew Chem Int Ed 48:5848–5852

    Google Scholar 

  43. Hashmi ASK, Pankajakshan S, Rudolph M, Enns E, Bander T, Rominger F, Frey W (2009) Adv Synth Catal 351:2855–2875

    Article  CAS  Google Scholar 

  44. Hashmi ASK (2010) Pure Appl Chem 82:1517–1528

    Article  CAS  Google Scholar 

  45. Hashmi ASK, Yang W, Rominger F (2011) Angew Chem 123:5882–5885; Angew Chem Int Ed 49:5762–5765

    Google Scholar 

  46. Arcadi A, Cerichelli G, Chiarini M, Di Giuseppe S, Marinelli F (2000) Tetrahedron Lett 41:9195–9198

    Article  CAS  Google Scholar 

  47. Ito H, Yajima T, Tateiwa J-i, Hosomi A (2000) Chem Commun 981–982

    Google Scholar 

  48. Echavarren AM, Nevado C (2004) Chem Soc Rev 33:431–436

    Article  CAS  Google Scholar 

  49. Bruneau C (2005) Angew Chem 117:2380–2386; Angew Chem Int Ed 44:2328–2334

    Google Scholar 

  50. Ma S, Yu S, Gu Z (2006) Angew Chem 118:206–209; Angew Chem Int Ed 45:200–203

    Google Scholar 

  51. Dyker G, Muth E, Hashmi ASK, Ding L (2003) Adv Synth Catal 345:1247–1252

    Article  CAS  Google Scholar 

  52. Hashmi ASK, Blanco MC (2006) Eur J Org Chem 4340–4342

    Google Scholar 

  53. Zhang L, Sun J, Kozmin SA (2006) Issue 348:2271–2296

    CAS  Google Scholar 

  54. Hashmi ASK, Sinha P (2004) Adv Synth Catal 346:432–438

    Article  Google Scholar 

  55. Hashmi ASK, Bührle M, Salathé R, Bats JW (2008) Adv Synth Catal 350:2059–2064

    Article  CAS  Google Scholar 

  56. Lin G-Y, C-w L, Hung S-H, Liu R-S (2008) Org Lett 10:5059–5062

    Article  CAS  Google Scholar 

  57. Nevado C (2010) Chimia 64:247–251

    Article  CAS  Google Scholar 

  58. Miki K, Ohe K, Uemura S (2003) Tetrahedron Lett 44:2019–2022

    Article  CAS  Google Scholar 

  59. Miki K, Ohe K, Uemura S (2003) J Org Chem 68:8505–8513

    Article  CAS  Google Scholar 

  60. Hashmi ASK, Rudolph M, Schymura S, Visus J, Frey W (2006) Eur J Org Chem 4905–4909

    Google Scholar 

  61. Weyrauch JP, Hashmi ASK, Schuster A, Hengst T, Schetter S, Littmann A, Rudolph M, Hamzic M, Visus J, Rominger F, Frey W, Bats JW (2010) Chem Eur J 16:956–963

    CAS  Google Scholar 

  62. Hashmi ASK, Weyrauch JP, Frey W, Bats JW (2004) Org Lett 6:4391–4394

    Article  CAS  Google Scholar 

  63. Hashmi ASK, Salathé R, Frey W (2007) Synlett 1763–1766

    Google Scholar 

  64. Hashmi ASK, Moliari L, Rominger F, Oeser T (2011) Eur J Org Chem 2256–2264

    Google Scholar 

  65. Hashmi ASK, Schuster AM, Schmuck M, Rominger F (2011) Eur J Org Chem 4595–4602

    Google Scholar 

  66. Hashmi ASK, Schuster AM, Litters S, Rominger F, Pernpointner M (2011) Chem Eur J 17:5661–5667

    Article  CAS  Google Scholar 

  67. Hashmi ASK, Schuster A, Rominger F (2009) Angew Chem 121:8396–8398; Angew Chem Int Ed 48:8247–8249

    Google Scholar 

  68. Hashmi ASK, Ramamurthi TD, Rominger F (2010) Adv Synth Catal 352:971–975

    Article  CAS  Google Scholar 

  69. Hashmi ASK, Schuster AM, Gaillard S, Cavallo L, Poater A, Nolan SP (2011) Organometallics 30:6328–6337

    Article  CAS  Google Scholar 

  70. Hashmi ASK, Blanco MC, Fischer D, Bats JW (2006) Eur J Org Chem 1387–1389

    Google Scholar 

  71. Hashmi ASK, Ramamurthi TD, Rominger F (2009) J Organomet Chem 694:592–597

    Article  CAS  Google Scholar 

  72. Hashmi ASK, Ramamurthi TD, Todd MH, Tsang AS-K, Graf K (2010) Aust J Chem 63:1619–1626

    Article  CAS  Google Scholar 

  73. Zhang G, Peng Y, Cui L, Zhang L (2009) Angew Chem 121:3158–3161; Angew Chem Int Ed 48:3112–3115

    Google Scholar 

  74. Hopkinson MN, Gee AD, Gouverneur V (2010) Isr J Chem 50:675–690

    Article  CAS  Google Scholar 

  75. Hashmi ASK, Lothschütz C, Döpp R, Rudolph M, Ramamurthi TD, Rominger F (2009) Angew Chem 121:8392–8395; Angew Chem Int Ed 48:8243–8246

    Google Scholar 

  76. Hashmi ASK, Döpp R, Lothschütz C, Rudolph M, Riedel D, Rominger F (2010) Adv Synth Catal 352:1307–1314

    Article  CAS  Google Scholar 

  77. Peña-López M, Ayán-Varela M, Sarandeses LA, Pérez Sestelo J (2010) Chem Eur J 16:9905–9909

    Article  Google Scholar 

  78. Hashmi ASK, Lothschütz C, Döpp R, Ackermann M, De Buck J, Rudolph M, Scholz C, Rominger F (2012) Adv Synth Catal 354:133–147

    Article  CAS  Google Scholar 

  79. González-Arellano C, Abad A, Corma A, García H, Iglesias M, Sánchez F (2007) Angew Chem 119:1558–1560; Angew Chem Int Ed 46:1536–1538

    Google Scholar 

  80. Li P, Wang L, Wang M, You F (2008) Eur J Org Chem 5946–5951

    Google Scholar 

  81. Corma A, Gutiérrez-Puebla E, Iglesias M, Monge A, Pérez-Ferreras S, Sánchez F (2006) Adv Synth Catal 348:1899–1907

    Article  CAS  Google Scholar 

  82. Lauterbach T, Livendahl M, Rosellón A, Espinet P, Echavarren AM (2010) Org Lett 13:3006–3009

    Article  Google Scholar 

  83. Corma A, Juárez R, Boronat M, Sánchez F, Iglesias M, García H (2011) Chem Commun 47:1446–1448

    Article  CAS  Google Scholar 

  84. Hashmi ASK, Molinari L (2011) Organometallics 30:3457–3460

    Article  CAS  Google Scholar 

  85. Hashmi ASK, Weyrauch JP, Rudolph M, Kurpejovic E (2004) Angew Chem 116:6707–6709; Angew Chem Int Ed 43:6545–6547

    Google Scholar 

  86. Hashmi ASK, Lothschuetz C, Ackermann M, Doepp R, Anantharaman S, Marchetti B, Bertagnolli H, Rominger F (2010) Chem Eur J 16:8012–8019

    Article  CAS  Google Scholar 

  87. Hashmi ASK, Loos A, Littmann A, Braun I, Knight J, Doherty S, Rominger F (2009) Adv Synth Catal 351:576–582

    Article  CAS  Google Scholar 

  88. Doherty S, Knight JG, Hashmi ASK, Smyth CH, Ward NAB, Robson KJ, Tweedley S, Harrington RW, Clegg W (2010) Organometallics 29:4139–4147

    Article  CAS  Google Scholar 

  89. Hashmi ASK, Loos A, Doherty S, Knight JG, Robson KJ, Rominger F (2011) Adv Synth Catal 353:749–759

    Article  CAS  Google Scholar 

  90. Khin C, Hashmi ASK, Rominger F (2010) Eur J Inorg Chem 1063–1069

    Google Scholar 

  91. Pažický M, Loos A, Ferreira MJ, Rominger F, Jäkel C, Hashmi ASK, Limbach M (2010) Organometallics 29:4448–4458

    Article  Google Scholar 

  92. Schäfer S, Frey W, Hashmi ASK, Cmrecki V, Luquin A, Laguna M (2010) Polyhedron 29:1925–1932

    Article  Google Scholar 

  93. Hashmi ASK, Hengst T, Lothschütz C, Rominger F (2010) Adv Synth Catal 352:1315–1337

    Article  CAS  Google Scholar 

  94. Hashmi ASK, Lothschütz C, Böhling C, Hengst T, Hubbert C, Rominger F (2010) Adv Synth Catal 352:3001–3012

    Article  CAS  Google Scholar 

  95. Hashmi ASK, Lothschütz C, Graf K, Häffner T, Schuster A, Rominger F (2011) Adv Synth Catal 354:1407–1412

    Article  Google Scholar 

  96. Hashmi ASK, Frost TM, Bats JW (2001) Org Lett 3:3769–3771

    Article  CAS  Google Scholar 

  97. Pernpointner M, Hashmi ASK (2009) J Chem Theory Comput 5:2717–2725

    Article  CAS  Google Scholar 

  98. Lein M, Rudolph M, Hashmi ASK, Schwerdtfeger P (2010) Organometallics 29:2206–2210

    Article  CAS  Google Scholar 

  99. Krauter CM, Hashmi ASK, Pernpointner M (2010) ChemCatChem 2:1226–1230

    Article  CAS  Google Scholar 

  100. Ye L, Wang Y, Aue DH, Zhang L (2012) J Am Chem Soc 134:31–34

    Article  CAS  Google Scholar 

  101. Hashmi ASK, Braun I, Rudolph M, Rominger F (2012) Organometallics 31:644–661

    Article  CAS  Google Scholar 

  102. Hashmi ASK, Braun I, Nösel P, Schädlich J, Wieteck M, Rudolph M, Rominger F (2012) Angew Chem 124:4532–4536; Angew Chem Int Ed 51:4456–4460

    Article  CAS  Google Scholar 

  103. Hashmi ASK, Wieteck M, Braun I, Nösel P, Jongbloed L, Rudolph M, RomingerR (2012) Adv Synth Catal 354:555–562

    Google Scholar 

  104. Hashmi ASK, Schwarz L, Rubenbauer P, Blanco MC (2006) Adv Synth Catal 348:705–708

    Article  CAS  Google Scholar 

  105. Hoffmann R (1982) Angew Chem 94:725–739; Angew Chem Int Ed Engl 12:711–724

    Google Scholar 

  106. Comyns AE (2001) Focus on Catalysts. Elsevier Advanced Technology

    Google Scholar 

  107. Comyns AE (2001) Focus on Catalysts, August 2001, Page 1

    Google Scholar 

  108. Comyns AE (2002) Focus on Catalysts 3: March 2002, Page 1–2. http://www.sciencedirect.com/science/journal/13514180/2002/3

  109. Comyns AE (2004) Focus on Catalysts 6: June 2004, Page 1. http://www.sciencedirect.com/science/journal/13514180/2004/6

  110. Andrew Mitchinson (Associate Editor, Nature). http://blogs.nature.com/thescepticalchymist/2007/04/endangered_elements_1.html

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Authors and Affiliations

  1. Organisch-Chemisches Institut, Ruprecht-Karls Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany

    A. Stephen K. Hashmi

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  1. A. Stephen K. Hashmi
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Correspondence to A. Stephen K. Hashmi .

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  1. , FB Chemie - Organische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Str. 54, Kaiserslautern, 67663, Germany

    Lukas J. Gooßen

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Hashmi, A.S.K. (2012). Gold-Catalyzed Organic Reactions. In: Gooßen, L. (eds) Inventing Reactions. Topics in Organometallic Chemistry, vol 44. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_2012_45

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