[go: up one dir, main page]
More Web Proxy on the site http://driver.im/
Skip to main content
Springer Nature Link
Log in

Sequentially Palladium-Catalyzed Processes

  • Chapter
  • First Online:
Metal Catalyzed Cascade Reactions

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 19))

Abstract

Sequentially palladium-catalyzed reactions consist of combinations of identical, related, or significantly different palladium-catalyzed processes that occur in a sequential or consecutive fashion in the same reaction vessel without addition of further amounts of catalyst to the reaction media. This novel type of cascade reaction can be elaborated into both domino and multicomponent processes and represents a significant contribution to the highly topical field of diversity-oriented synthesis.

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

Access this chapter

Log in via an institution

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Similar content being viewed by others

Abbreviations

Ac:

Acetyl

AcO:

Acetyloxy

Ar:

Aryl

BINAP:

2,2′-Bis(diphenyl)phosphano)-1,1′-binaphthyl

Boc:

tert-Butyloxycarbonyl

Bn:

Benzyl

Bu:

Butyl

cat:

Catalyst

Cbz:

Carbonyloxybenzyl

dba:

Dibenzylideneacetone

DMA:

N,N-Dimethylacetamide

DMF:

N,N-Dimethylformamide

DME:

1,2-Dimethoxyethane

dppe:

1,2-Bis(diphenylphosphanyl)ethane

dppf:

1,1′-Bis(diphenylphosphano)ferrocene

dppm:

Bis(diphenylphosphanyl)methane

EWG:

Electron-withdrawing group

Et:

Ethyl

Hal:

Halogen

L:

Ligand

Me:

Methyl

NMP:

N-Methylpyrrolidone

Nu:

Nucleophile

Oct:

Octyl

Ph:

Phenyl

Pr:

Propyl

PTSA:

p-Toluenesulfonic acid

R:

Organic substituent

TBAB:

Tetra-n-butylammonium bromide

TBAF:

Tetra-n-butylammonium fluoride

THF:

Tetrahydrofuran

THP:

Tetrahydropyranyl

TBDMS:

tert-Butyldimethylsilyl

Tol:

Tolyl

Ts:

p-Tolylsulfonyl

TMS:

Trimethylsilyl

References

  1. Fogg DE, de Santos EN (2004) Coord Chem Rev 248:2365

    CAS  Google Scholar 

  2. Kirsch G, Hesse S, Comel A (2004) Curr Org Synth 1:47

    CAS  Google Scholar 

  3. Nakamura I, Yamamoto Y (2004) Chem Rev 104:2127

    CAS  Google Scholar 

  4. Balme G, Bossharth E, Monteiro N (2003) Eur J Org Chem, p 4101

    Google Scholar 

  5. de Meijere A, Schelper M (2003) Actual Chim, p 51

    Google Scholar 

  6. Battistuzzi G, Cacchi S, Fabrizi G (2002) Eur J Org Chem, p 2671

    Google Scholar 

  7. Poli G, Giambastiani G, Heumann A (2000) Tetrahedron 56:5959

    CAS  Google Scholar 

  8. Grigg R, Sridharan V (1999) J Organomet Chem 576:65

    CAS  Google Scholar 

  9. de Meijere A, Bräse S (1999) J Organomet Chem 576:88

    Google Scholar 

  10. Molander GA, Harris CR (1996) Chem Rev 96:307

    CAS  Google Scholar 

  11. Malacria M (1996) Chem Rev 96:289

    CAS  Google Scholar 

  12. Tietze LF (1996) Chem Rev 96:115

    CAS  Google Scholar 

  13. Tietze LF, Beifuss U (1993) Angew Chem 105:137

    CAS  Google Scholar 

  14. Tietze LF, Beifuss U (1993) Angew Chem Int Ed Engl 32:131

    Google Scholar 

  15. Tietze LF (1990) J Heterocycl Chem 27:47

    Article  CAS  Google Scholar 

  16. Wasilke J, Obrey SJ, Baker RT, Bazan GC (2005) Chem Rev 105:1001

    CAS  Google Scholar 

  17. Ajamian A, Gleason JL (2004) Angew Chem 116:3842

    Google Scholar 

  18. Ajamian A, Gleason JL (2004) Angew Chem Int Ed 43:3754

    CAS  Google Scholar 

  19. Yamamoto Y, Nakagai Y, Itoh K (2004) Chem Eur J 10:231

    CAS  Google Scholar 

  20. Cossy J, Bargiggia F, BouzBouz S (2003) Org Lett 5:459

    CAS  Google Scholar 

  21. Thadani AN, Rawal VH (2002) Org Lett 4:4317

    CAS  Google Scholar 

  22. Son SU, Park KH, Chung YK (2002) J Am Chem Soc 124:6838

    CAS  Google Scholar 

  23. Louie J, Bielawski CW, Grubbs RH (2001) J Am Chem Soc 123:11312

    CAS  Google Scholar 

  24. Evans PA, Robinson JE (2001) J Am Chem Soc 123:4609

    CAS  Google Scholar 

  25. Cacchi S (1999) J Organomet Chem 576:42

    CAS  Google Scholar 

  26. Negishi E, Copéret C, Ma S, Liou S, Liu F (1996) Chem Rev 96:365

    CAS  Google Scholar 

  27. Schreiber SL, Burke MD (2004) Angew Chem 116:48

    Google Scholar 

  28. Schreiber SL, Burke MD (2004) Angew Chem Int Ed 43:46

    Google Scholar 

  29. Burke MD, Berger EM, Schreiber SL (2003) Science 302:613

    CAS  Google Scholar 

  30. Arya P, Chou DTH, Baek MG (2001) Angew Chem 113:351

    Google Scholar 

  31. Arya P, Chou DTH, Baek MG (2001) Angew Chem Int Ed 40:339

    CAS  Google Scholar 

  32. Cox B, Denyer JC, Binnie A, Donnelly MC, Evans B, Green DVS, Lewis JA, Mander TH, Merritt AT, Valler MJ, Watson SP (2000) Progr Med Chem 37:83

    Article  CAS  Google Scholar 

  33. Schreiber SL (2000) Science 287:1964

    CAS  Google Scholar 

  34. Bräse S, de Meijere A (2004) Cross-coupling of organyl halides with alkenes: the Heck reaction. In: de Meijere A, Diederich F (eds) Metal-catalyzed cross-coupling reactions. Wiley, Weinheim, p 217

    Google Scholar 

  35. Beletskaya IP, Cheprakov AV (2000) Chem Rev 100:3009

    CAS  Google Scholar 

  36. Crisp GT (1998) Chem Soc Rev 27:427

    CAS  Google Scholar 

  37. Cabri W, Candiani I (1995) Acc Chem Res 28:2

    CAS  Google Scholar 

  38. de Meijere A, Meyer FE (1994) Angew Chem 106:2473

    Google Scholar 

  39. de Meijere A, Meyer FE (1994) Angew Chem Int Ed Engl 33:2379

    Google Scholar 

  40. Heck RF (1982) Org React 27:345

    CAS  Google Scholar 

  41. Link JT, Overman LE (1998) Intramolecular Heck reactions in natural product chemistry. In: de Meijere A, Diederich F (eds) Metal-catalyzed cross-coupling reactions. Wiley, Weinheim, p 231

    Google Scholar 

  42. Gruber M, Chouzier S, Koehler K, Djakovitch L (2004) Appl Cat A General 265:161

    CAS  Google Scholar 

  43. Kamei T, Itami K, Yoshida J (2004) Adv Synth Catal 346:1824

    CAS  Google Scholar 

  44. Itami K, Ushiogi Y, Nokami T, Ohashi Y, Yoshida J (2004) Org Lett 6:3695

    CAS  Google Scholar 

  45. Itami K, Mineno M, Muraoka N, Yoshida J (2004) J Am Chem Soc 126:11778

    CAS  Google Scholar 

  46. Itami K, Kamei T, Yoshida J (2003) J Am Chem Soc 125:14670

    CAS  Google Scholar 

  47. Itami K, Nokami T, Ishimura Y, Mitsudo K, Kamei T, Yoshida J (2001) J Am Chem Soc 123:11577

    CAS  Google Scholar 

  48. Itami K, Nokami T, Yoshida J (2001) J Am Chem Soc 123:5600

    CAS  Google Scholar 

  49. Itami K, Mitsudo K, Kamei T, Koike T, Nokami T, Yoshida J (2000) J Am Chem Soc 122:12013

    CAS  Google Scholar 

  50. Hatanaka Y, Hiyama T (1991) Synlett, p 845

    Google Scholar 

  51. Hiyama T (1998) Organosilicon compounds in cross-coupling reactions. In: de Meijere A, Diederich F (eds) Metal-catalyzed cross-coupling reactions. Wiley, Weinheim, p 421

    Google Scholar 

  52. Hiyama T, Shirakawa E (2002) Top Curr Chem 219:61

    CAS  Google Scholar 

  53. Denmark SE, Sweis RF (2002) Chem Pharm Bull 50:1531

    CAS  Google Scholar 

  54. Kraft A, Grimsdale AC, Holmes AB (1998) Angew Chem 110:416

    Google Scholar 

  55. Kraft A, Grimsdale AC, Holmes AB (1998) Angew Chem Int Ed 37:403

    CAS  Google Scholar 

  56. Sheats JR, Barbara PF (1999) Acc Chem Res 32:191

    CAS  Google Scholar 

  57. Friend RH, Gymer RW, Holmes AB, Burroughes JH, Marks RN, Taliani C, Bradley DCC, Dos Santos DA, Brédas JL, Lögdlund M, Salaneck WR (1999) Nature 397:121

    CAS  Google Scholar 

  58. Martin RE, Diederich F (1999) Angew Chem 111:1440–1469

    Google Scholar 

  59. Martin RE, Diederich F (1999) Angew Chem Int Ed 38:1351

    CAS  Google Scholar 

  60. Segura JL, Martín N (2000) J Mater Chem 10:2403

    CAS  Google Scholar 

  61. Meier H (1992) Angew Chem 104:1425

    CAS  Google Scholar 

  62. Meier H (1992) Angew Chem Int Ed Engl 31:1437

    Google Scholar 

  63. Itami K, Tonogaki K, Ohashi Y, Yoshida J (2004) Org Lett 6:4093

    CAS  Google Scholar 

  64. Yamazaki K, Nakamura Y, Kondo Y (2002) J Chem Soc Perkin Trans 1:2137

    Google Scholar 

  65. Kondo Y, Inamoto K, Sakamoto T (2000) J Comb Chem 2:232

    CAS  Google Scholar 

  66. Lee C, Oh KS, Kim KS, Ahn KH (2000) Org Lett 2:1213

    CAS  Google Scholar 

  67. Catellani M (2002) Pure Appl Chem 74:63

    CAS  Google Scholar 

  68. Catellani M, Cugini F (1999) Tetrahedron 55:6595

    CAS  Google Scholar 

  69. Catellani M, Motti E (1998) New J Chem 759

    Google Scholar 

  70. Catellani M, Motti E, Baratta S (2001) Org Lett 3:3611

    CAS  Google Scholar 

  71. Alberico D, Paquin J, Lautens M (2005) Tetrahedron 61:6283

    CAS  Google Scholar 

  72. Ferraccioli R, Carenzi D, Catellani M (2004) Tetrahedron Lett 45:6903

    CAS  Google Scholar 

  73. Ferraccioli R, Carenzi D, Rombolà O, Catellani M (2004) Org Lett 6:4759

    CAS  Google Scholar 

  74. Lautens M, Paquin J, Piguel S, Dahlmann M (2001) J Org Chem 66:8127

    CAS  Google Scholar 

  75. Lautens M, Paquin J, Piguel S (2002) J Org Chem 67:3972

    CAS  Google Scholar 

  76. Pache S, Lautens M (2003) Org Lett 5:4827

    CAS  Google Scholar 

  77. Trost BM (1996) Acc Chem Res 29:355

    CAS  Google Scholar 

  78. Trost BM, Van Vranken DL (1996) Chem Rev 96:395

    CAS  Google Scholar 

  79. Pfaltz A (1993) Acc Chem Res 26:339

    CAS  Google Scholar 

  80. Organ MG, Cooper JT, Rogers LR, Soleymanzadeh F, Paul T (2000) J Org Chem 65:7959

    CAS  Google Scholar 

  81. Uozumi Y, Tanahashi A, Hayashi T (1993) J Org Chem 58:6826

    CAS  Google Scholar 

  82. Lemaire S, Prestat G, Giambastiani G, Madec D, Pacini B, Poli G (2003) J Organomet Chem 687:291

    CAS  Google Scholar 

  83. Itami K, Yamazaki D, Yoshida J (2003) Org Lett 5:2161

    CAS  Google Scholar 

  84. Watson SP, Knox GR, Heron NM (1994) Tetrahedron Lett 35:9763

    CAS  Google Scholar 

  85. Gabriele B, Mancuso R, Salerno G, Veltri L (2005) Chem Commun: 271

    Google Scholar 

  86. Wolfe JP, Wagaw S, Marcoux J, Buchwald SL (1998) Acc Chem Res 31:805

    CAS  Google Scholar 

  87. Hartwig JF (1998) Angew Chem 110:2154

    Google Scholar 

  88. Hartwig JF (1998) Angew Chem Int Ed 37:2046

    CAS  Google Scholar 

  89. Yang BH, Buchwald SL (1999) J Organomet Chem 576:125

    CAS  Google Scholar 

  90. Muci AR, Buchwald SL (2002) Practical palladium catalysts for C-N and C-O bond formation. In: Miyaura N (ed) Cross-coupling reaction: a practical guide. Topics in current chemistry, vol 219. Springer, Berlin Heidelberg New York

    Google Scholar 

  91. Schlummer B, Scholz U (2004) Adv Synth Catal 346:1599

    CAS  Google Scholar 

  92. Thayumanavan S, Barlow S, Marder SR (1997) Chem Mater 9:3231

    CAS  Google Scholar 

  93. Loones KTJ, Maes BUW, Dommisse RA, Lemière GLF (2004) Chem Commun: 2466

    Google Scholar 

  94. Nandakumar MV, Verkade JG (2005) Angew Chem 117:3175

    Google Scholar 

  95. Nandakumar MV, Verkade JG (2005) Angew Chem Int Ed 44:3115

    CAS  Google Scholar 

  96. Stauffer SR, Steinbeiser MA (2005) Tetrahedron Lett 46:2571

    CAS  Google Scholar 

  97. Willis MC, Brace GN, Holmes IP (2005) Angew Chem 117:407

    Google Scholar 

  98. Willis MC, Brace GN, Holmes IP (2005) Angew Chem Int Ed 44:403

    CAS  Google Scholar 

  99. Bedford RB, Cazin CSJ (2002) Chem Commun: 2310

    Google Scholar 

  100. Mátyus P, Maes BUW, Riedl Z, Hajós G, Lemière GLF, Tapolcsányi P, Monsieurs K, Éliás O, Dommisse RA, Krajsovszkya G (2004) Synlett, p 1123

    Google Scholar 

  101. Dajka-Halász B, Monsieurs K, Éliás O, Károlyházy L, Tapolcsányi P, Maes BUW, Riedl Z, Hajós G, Dommisse RA, Lemière GLF, Košmrlj J, Mátyus P (2004) Tetrahedron 60:2283

    Google Scholar 

  102. Lira R, Wolfe JP (2004) J Am Chem Soc 126:13906

    CAS  Google Scholar 

  103. Yang Q, Ney JE, Wolfe JP (2005) Org Lett 7:2575

    CAS  Google Scholar 

  104. Omar-Amrani R, Schneider R, Fort Y (2004) Synthesis, p 2527

    Google Scholar 

  105. Thielges S, Meddah E, Bisseret P, Eustache J (2004) Tetrahedron Lett 45:907

    CAS  Google Scholar 

  106. Sonogashira K (1998) Cross-coupling reactions to sp carbon atoms. In: de Meijere A, Diederich F (eds) Metal-catalyzed cross-coupling reactions. Wiley, Weinheim, p 203

    Google Scholar 

  107. Sonogashira K (2002) J Organomet Chem 653:46

    CAS  Google Scholar 

  108. Negishi E, Anastasia L (2003) Chem Rev 103:1979

    CAS  Google Scholar 

  109. Pal M, Subramanian V, Batchu VR, Dager I (2004) Synlett, p 1965

    Google Scholar 

  110. Kotora M, Negishi E (1997) Synthesis, p 121

    Google Scholar 

  111. Fiandanese V, Bottalico D, Marchese G (2001) Tetrahedron 57:10213

    CAS  Google Scholar 

  112. Fiandanese V, Bottalico D, Marchese G, Punzi A (2004) Tetrahedron 60:11421

    CAS  Google Scholar 

  113. Kawasaki T, Yamamoto Y (2002) J Org Chem 67:5138

    CAS  Google Scholar 

  114. Karpov AS, Merkul E, Oeser T, Müller TJJ (2005) Chem Commun: 2581

    Google Scholar 

  115. Müller TJJ, Ansorge M, Aktah D (2000) Angew Chem 112:1323

    Google Scholar 

  116. Müller TJJ, Ansorge M, Aktah D (2000) Angew Chem Int Ed 39:1253

    Google Scholar 

  117. Braun RU, Müller TJJ (2003) Mol Diversity 6:251

    CAS  Google Scholar 

  118. Tsuji J (1995) Palladium reagents and catalysts – innovations in organic synthesis. Wiley, Chichester, Chap. 6.4

    Google Scholar 

  119. Stille JK (1985) Pure Appl Chem 57:1771

    CAS  Google Scholar 

  120. Stille JK (1986) Angew Chem 98:504

    CAS  Google Scholar 

  121. Stille JK (1986) Angew Chem Int Ed Engl 25:508

    Google Scholar 

  122. Stille JK, Groh BL (1987) J Am Chem Soc 109:813

    CAS  Google Scholar 

  123. Farina V, Krishnamurthy V, Scott WJ (1997) Org React 50:1

    CAS  Google Scholar 

  124. Gallagher WP, Terstiege I, Maleczka RE Jr (2001) J Am Chem Soc 123:3194

    CAS  Google Scholar 

  125. Maleczka RE Jr, Gallagher WP, Terstiege I (2000) J Am Chem Soc 122:384

    CAS  Google Scholar 

  126. Hitchcock SA, Mayhugh DR, Gregory GS (1995) Tetrahedron Lett 36:9085

    CAS  Google Scholar 

  127. Mori M, Kaneta N, Shibasaki M (1991) J Org Chem 56:3486

    CAS  Google Scholar 

  128. Kang S, Ha Y, Ko B, Lim Y, Jung J (2002) Angew Chem 114:353

    Google Scholar 

  129. Kang S, Ha Y, Ko B, Lim Y, Jung J (2002) Angew Chem Int Ed 41:343

    CAS  Google Scholar 

  130. Ferreira ICFR, Queiroz MRP, Kirsch G (2003) Tetrahedron Lett 44:4327

    CAS  Google Scholar 

  131. Kabalka GW, Yao M (2003) Tetrahedron Lett 44:7885

    CAS  Google Scholar 

  132. Dyker G (1998) Coupling reactions involving CH activation. In: Beller M, Bolm C (eds) Transition metals for organic synthesis. Wiley, Weinheim, 1:241

    Google Scholar 

  133. Dyker G (1999) Angew Chem 111:1808

    Google Scholar 

  134. Dyker G (1999) Angew Chem Int Ed 38:1698

    Google Scholar 

  135. Kakiuchi F, Murai S (1999) Top Organomet Chem 3:47

    CAS  Google Scholar 

  136. Murahashi S, Takaya H (2000) Acc Chem Res 33:225

    CAS  Google Scholar 

  137. Dyker G (2005) Handbook of C - H transformations. Wiley, Weinheim

    Google Scholar 

  138. Campo MA, Huang Q, Yao T, Tian Q, Larock RC (2003) J Am Chem Soc 125:11506

    CAS  Google Scholar 

  139. Bacchi A, Chiusoli GP, Costa M, Gabriele B, Righi C, Salerno G (1997) Chem Commun: 1209

    Google Scholar 

  140. Gabriele B, Salerno G, Plastina P, Costa M, Crespini A (2004) Adv Synth Catal 346:351

    CAS  Google Scholar 

  141. Gabriele B, Salerno G, Veltri L, Costa M (2001) J Organomet Chem 622:84

    CAS  Google Scholar 

  142. Trost BM (1990) Acc Chem Res 23:34

    CAS  Google Scholar 

  143. Trost BM (1991) Janssen Chim Acta 9:3

    CAS  Google Scholar 

  144. Trost BM, Krische MJ (1998) Synlett, p 1

    Google Scholar 

  145. Lloyd-Jones GC (2003) Org Biomol Chem, p 215

    Google Scholar 

  146. Aubert C, Buisine O, Malacria M (2002) Chem Rev 102:813

    CAS  Google Scholar 

  147. Yamada H, Aoyagi S, Kibayashi C (1997) Tetrahedron Lett 38:3027

    CAS  Google Scholar 

  148. Kressierer CJ, Müller TJJ (2005) Org Lett 7:2237

    CAS  Google Scholar 

  149. Culkin DA, Hartwig JF (2003) Acc Chem Res 36:234

    CAS  Google Scholar 

  150. Liu X, Hartwig JF (2004) J Am Chem Soc 126:5182

    CAS  Google Scholar 

  151. Fox JM, Huang X, Chieffi A, Buchwald SL (2000) J Am Chem Soc 122:1360

    CAS  Google Scholar 

  152. Mutter R, Martin de la Neva EM, Wills M (2000) Chem Commun: 1675

    Google Scholar 

  153. Varseev GN, Maier ME (2005) Org Lett 7:3881

    CAS  Google Scholar 

  154. Trost BM, Sorum MT, Chan C, Harms AE, Ruhter G (1997) J Am Chem Soc 119:698

    CAS  Google Scholar 

  155. Trost BM, McIntosh MC (1995) J Am Chem Soc 117:7255

    CAS  Google Scholar 

  156. Trost BM, Frontier AJ (2000) J Am Chem Soc 122:11727

    CAS  Google Scholar 

  157. Gevorgyan V, Radhakrishnan U, Takeda A, Rubina M, Rubin M, Yamamoto Y (2001) J Org Chem 66:2835

    CAS  Google Scholar 

  158. Saito S, Yamamoto Y (2000) Chem Rev 100:2901

    CAS  Google Scholar 

  159. Gevorgyan V, Yamamoto Y (1999) J Organomet Chem 576:232

    CAS  Google Scholar 

  160. Thadani AN, Rawal VH (2002) Org Lett 4:4321

    CAS  Google Scholar 

  161. Jeevanandam A, Narkunan K, Ling Y (2001) J Org Chem 66:6014

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

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

    Thomas J. J. Müller

Authors
  1. Thomas J. J. Müller
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Thomas J. J. Müller .

Editor information

Thomas J. J. Müller

Rights and permissions

Reprints and permissions

About this chapter

Cite this chapter

Müller, T.J.J. Sequentially Palladium-Catalyzed Processes. In: Müller, T.J.J. (eds) Metal Catalyzed Cascade Reactions. Topics in Organometallic Chemistry, vol 19. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_012

Download citation

Publish with us

Policies and ethics

Search

Navigation