SpringerLink
Log in

Palladium-Catalyzed Cyclization via Carbopalladation and Acylpalladation

  • Chapter
  • First Online:
Metal Catalyzed Cascade Reactions

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

  • 861 Accesses

Abstract

Over the past two decades, cyclic carbopalladation and related cyclic acylpalladation of alkenes, allenes, alkynes, and related π complexes including the cyclic Heck reaction have been developed into new and attractive synthetic methods. This chapter mainly discusses catalytic cyclization reactions via cyclic carbopalladation and cyclic acylpalladation, which may not be classified under the cyclic Heck reaction.

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

References

  1. Negishi E (2002) Fundamental Properties of Palladium and Patterns of the Reactions of Palladium and Its Complexes. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 17

    Google Scholar 

  2. Negishi E (2002) General Discussion of the Methods of Synthesis and in situ Generation of Organopalladium Compounds. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 127

    Google Scholar 

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

    CAS  Google Scholar 

  4. Mizoroki T, Mori K, Ozaki A (1971) Bull Chem Soc Jpn 44:581

    CAS  Google Scholar 

  5. Heck RF, Nolley JP (1972) J Org Chem 37:2320

    CAS  Google Scholar 

  6. Heck RF (1968) J Am Chem Soc 90:5518

    CAS  Google Scholar 

  7. Blomquist AT, Maitlis PM (1962) J Am Chem Soc 84:2329

    CAS  Google Scholar 

  8. Maitlis PM (1976) Acc Chem Res 9:93

    CAS  Google Scholar 

  9. Grigg R, Stevenson P, Worakun T (1984) J Chem Soc Chem Commun, p 1073

    Google Scholar 

  10. Tour JM, Negishi E (1985) J Am Chem Soc 107:8289

    CAS  Google Scholar 

  11. Zhang Y, Negishi E (1989) J Am Chem Soc 111:3454

    CAS  Google Scholar 

  12. Ma S, Lu X (1991) J Org Chem 56:5120

    CAS  Google Scholar 

  13. Lu X (2002) Palladium-Catalyzed Reaction via Halopalladation of π-Compounds. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 2267

    Google Scholar 

  14. Burns B, Grigg R, Ratananukul P, Sridharan V, Stevenson P, Sukirthalingam S, Worakun T (1988) Tetrahedron Lett 29:5565

    CAS  Google Scholar 

  15. Burns B, Grigg R, Sridharan V, Stevenson P, Sukirthalingam S, Worakun T (1989) Tetrahedron Lett 30:1135

    CAS  Google Scholar 

  16. Larock RC, Fried CA (1990) J Am Chem Soc 112:5882

    CAS  Google Scholar 

  17. Burns B, Grigg R, Ratananukul P, Sridharan V, Stevenson P, Worakun T (1988) Tetrahedron Lett 29:4329

    CAS  Google Scholar 

  18. Narula CK, Mak KT, Heck RF (1983) J Org Chem 48:2792

    CAS  Google Scholar 

  19. Shi L, Narula CK, Mak KT, Kao L, Lu Y, Heck RF (1983) J Org Chem 48:3894

    CAS  Google Scholar 

  20. Overman LE (1992) Pure Appl Chem 64:1813

    CAS  Google Scholar 

  21. Abelman MM, Overman LE (1988) J Am Chem Soc 110:2328

    CAS  Google Scholar 

  22. Balme G, Bouyssi D (1994) Tetrahedron 50:403

    CAS  Google Scholar 

  23. Balme G, Bouyssi D, Monteiro N (2002) Palladium-Catalyed Reactions Involving Attack on Palladium-Alkene, Palladium-Alkyne, and Related π-Complexes by Carbon Nucleophiles. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 2245

    Google Scholar 

  24. Tsuji J, Hosaka S (1965) J Polym Lett 3:705

    Google Scholar 

  25. Brewis S, Hughes PR (1965) J Chem Soc Chem Commun, p 489

    Google Scholar 

  26. Brewis S, Hughes PR (1966) J Chem Soc Chem Commun, p 6

    Google Scholar 

  27. Sen A (1993) Acc Chem Res 26:303

    CAS  Google Scholar 

  28. Drent E, Budzelaar PHM (1996) Chem Rev 96:663

    CAS  Google Scholar 

  29. Consiglio G (2002) Polymeric Acylpalladation. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 2559

    Google Scholar 

  30. Negishi E, Miller JA (1983) J Am Chem Soc 105:6761

    CAS  Google Scholar 

  31. Shimoyama I, Zhang Y, Wu G, Negishi E (1990) Tetrahedron Lett 31:2841

    CAS  Google Scholar 

  32. Negishi E, Tour JM (1986) Tetrahedron Lett 27:4869

    CAS  Google Scholar 

  33. Roberto D, Catellani M, Chiusoli GP (1988) Tetrahedron Lett 29:2115

    CAS  Google Scholar 

  34. Negishi E, Zhang Y, Shimoyama I, Wu G (1989) J Am Chem Soc 111:8018

    CAS  Google Scholar 

  35. Negishi E, Copéret C, Sugihara T, Shimoyama I, Zhang Y, Wu G, Tour JM (1994) Tetrahedron 50:425

    CAS  Google Scholar 

  36. Negishi E, Liou SY, Xu C, Shimoyama I, Makabe H (1999) J Mol Cat A 143:279

    CAS  Google Scholar 

  37. Negishi E, Makabe H (2002) Reactions of Acylpalladium Derivatives with Enolates and Related Amphiphilic Reagents. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 2455

    Google Scholar 

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

    CAS  Google Scholar 

  39. Negishi E (1992) Pure Appl Chem 74:323

    Google Scholar 

  40. Negishi E, de Meijere A (eds) (2002) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 3279

    Google Scholar 

  41. Bräse S, de Meijere A (2002) Synthesis of Carbocycles. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1223

    Google Scholar 

  42. Dyker G (2002) Synthesis of Heterocycles. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1255

    Google Scholar 

  43. Shibasaki M, Miyazaki F (2002) Asymmetric Heck Reactions. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1283

    Google Scholar 

  44. Kozhushkov SI, de Meijere A (2002) Carbopalladation of Alkenes not Accompanied by Dehydropalladation. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1317

    Google Scholar 

  45. Cacchi S, Fabrizi G (2002) Carbopalladation of Alkynes Followed by Trap** with Nucleophilic Reagents. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1335

    Google Scholar 

  46. Gevorgyan V, Yamamoto Y (2002) Carbopalladation of Alkynes Followed by Trap** with Electrophiles. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1361

    Google Scholar 

  47. Bräse S, de Meijere A (2002) Palladium-Catalyzed Cascade Carbopalladation: Termination with Alkenes, Arenes, and Related π-Bond Systems. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1369

    Google Scholar 

  48. Bräse S, de Meijere A (2002) Palladium-Catalyzed Cascade Carbopalladation: Termination by Nucleophilic Reagents. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1405

    Google Scholar 

  49. Negishi E, Copéret C (2002) Palladium-Catalyzed Tandem and Cascade Carbopalladation of Alkynes and 1,1-Disubstituted Alkenes Terminated by Carbonylative Reactions. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1431

    Google Scholar 

  50. Takahashi T, Doi T (2002) Allylpalladation and Related Reactions of Alkenes, Alkynes, Dienes, and Other π-Compounds. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1449

    Google Scholar 

  51. Gevorgyan V (2002) Alkynyl Substitution Via Alkynylpalladation-Reductive Elimination. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1463

    Google Scholar 

  52. Suzuki K, Ohmori K (2002) Arene Analogs of the Heck Reaction. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1471

    Google Scholar 

  53. Ma S (2002) Carbopalladation of Allenes. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1491

    Google Scholar 

  54. Takacs JM (2002) Palladium-Catalyzed Oligomerization and Polymerization of Dienes and Related Compounds. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1579

    Google Scholar 

  55. Saito S, Yamamoto Y (2002) Palladium-Catalyzed Benzannulation Reactions of Conjugated Enynes and Diynes. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1635

    Google Scholar 

  56. Knochel P (2002) Palladium-Catalyzed Carbozincation. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1651

    Google Scholar 

  57. Link JT (2002) Synthesis of Natural Products via Carbopalladation. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1523

    Google Scholar 

  58. Copéret C, Negishi E (2002) Intramolecular Acylpalladation: Intramolecular Acylpalladation Reactions with Alkenes, Alkynes, and Related Unsaturated Compounds. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 2519

    Google Scholar 

  59. Ishii Y, Hidai M (2002) Intramolecular Acylpalladation: Intramolecular Acylpalladation with Arenes. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 2553

    Google Scholar 

  60. Mori M (2002) Synthesis of Natural Products via Palladium-Catalyzed Carbonylation. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 2663

    Google Scholar 

  61. Copéret C (2002) Other Intermolecular Acylpalladation. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 2577

    Google Scholar 

  62. Okumoto H (2002) Formation and Reactions of Ketenes Generated via Acylpalladium Derivatives. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 2655

    Google Scholar 

  63. Qwczarczyk Z, Lamaty F, Vawter EJ, Negishi E (1992) J Am Chem Soc 114:10091

    Google Scholar 

  64. Brown S, Clarkson S, Grigg R, Sridharan V (1993) Tetrahedron Lett 34:157

    CAS  Google Scholar 

  65. Terakado M, Miyazawa M, Yamamoto K (1994) Synlett 134. For results showing the opposite stereochemical outcome, see: Trost BM, Dumas J (1993) Tetrahedron Lett 34:19

    Google Scholar 

  66. Catellani M, Chiusoli GP, Cirodini W, Salerno G (1980) J Organomet Chem 199:C21

    CAS  Google Scholar 

  67. Negishi E, Ma S, Amanfu J, Copéret C, Miller JA, Tour JM (1996) J Am Chem Soc 118:5919

    CAS  Google Scholar 

  68. Grigg R, Sridharan V, Sukirthalingam S (1991) Tetrahedron Lett 32:3855

    CAS  Google Scholar 

  69. Steining AG, de Meijere A (1999) Eur J Org Chem, p 1333

    Google Scholar 

  70. Schweizer S, Song ZZ, Meyer FE, Parsons PJ, de Meijere A (1999) Angew Chem Int Ed 38:1452

    CAS  Google Scholar 

  71. Carpenter NE, Kucera DJ, Overman LE (1989) J Org Chem 54:5846

    CAS  Google Scholar 

  72. Grigg R, Sridharan V (1992) Tetrahedron Lett 33:7965

    CAS  Google Scholar 

  73. Sato Y, Sodeoka M, Shibasaki M (1989) J Org Chem 54:4738

    CAS  Google Scholar 

  74. Ashimori A, Matsuura T, Overman LE, Poon DJ (1993) J Org Chem 58:6949

    CAS  Google Scholar 

  75. Matsuura T, Overman LE, Poon DJ (1998) J Am Chem Soc 120:6500

    CAS  Google Scholar 

  76. Maddaford SP, Anderson NG, Cristofoli WA, Keay BA (1996) J Am Chem Soc 118:10766

    CAS  Google Scholar 

  77. Kondo K, Sodeoka M, Mori M, Shibasaki M (1993) Tetrahedron Lett 34:4219

    CAS  Google Scholar 

  78. Ohrai K, Kondo K, Sodeoka M, Shibasaki M (1994) J Am Chem Soc 116:11737

    CAS  Google Scholar 

  79. Ohshima T, Kagechika K, Adachi M, Sedeoka M, Shibasaki (1996) J Am Chem Soc 118:7108

    CAS  Google Scholar 

  80. Hatano M, Terada M, Mikami K (2001) Angew Chem Int Ed 40:249

    CAS  Google Scholar 

  81. Ma S, Negishi E (1995) J Am Chem Soc 117:6345

    CAS  Google Scholar 

  82. Ma S, Negishi E (1994) J Org Chem 59:4730

    CAS  Google Scholar 

  83. Wang RT, Chou FL, Luo FT (1990) J Org Chem 55:4846

    CAS  Google Scholar 

  84. Negishi E, Noda Y, Lamaty F, Vawter EJ (1990) Tetrahedron Lett 31:4393

    CAS  Google Scholar 

  85. Nuss JM, Levine BH, Rennels RA, Heravi MM (1991) Tetrahedron Lett 32:5243

    CAS  Google Scholar 

  86. Nuss JM, Rennels RA, Levine BH (1993) J Am Chem Soc 115:6991

    CAS  Google Scholar 

  87. Torii S, Okumoto H, Tadokoro T, Nishimura A, Rashid MA (1993) Tetrahedron Lett 34:2139

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  89. Oh CH, Lim YM (2003) Tetrahedron 44:267

    CAS  Google Scholar 

  90. Salem B, Klotz P, Suffert J (2003) Org Lett 5:845

    CAS  Google Scholar 

  91. Zhu G, Zhang Z (2003) Org Lett 5:3645

    CAS  Google Scholar 

  92. Zhu G, Tong X, Cheng J, Sun Y, Li D, Zhang Z (2005) J Org Chem 70:1712

    CAS  Google Scholar 

  93. Zhu G, Zhang Z (2004) Org Lett 6:4041

    CAS  Google Scholar 

  94. Salem B, Delort E, Klotz P, Suffert J (2003) Org Lett 5:2307

    CAS  Google Scholar 

  95. Couty S, Liégault B, Meyer C, Cossy J (2004) Org Lett 6:2511

    CAS  Google Scholar 

  96. Böhmer J, Grigg R, Marchbank JD (2002) Chem Commun, p 768

    Google Scholar 

  97. Barberan O, Alami M, Brion JD (2001) Tetrahedron Lett 42:2657

    CAS  Google Scholar 

  98. Oh CH, Park SJ (2003) Tetrahedron Lett 44:3785

    CAS  Google Scholar 

  99. Tsuji J, Takahashi H, Morikawa M (1965) Tetrahedron Lett, p 4387

    Google Scholar 

  100. Hata G, Takahashi K, Miyake A (1970) Chem Commun, p 1392

    Google Scholar 

  101. Atkins KE, Walker WE, Manyik RM (1970) Tetrahedron Lett, p 3821

    Google Scholar 

  102. Trost BM, Fullerton TJ (1973) J Am Chem Soc 95:292

    CAS  Google Scholar 

  103. Tsuji J (2002) Overview of the Palladium-Catalyzed Carbon–Carbon Bond Formation via π-Allylpalladium and Propargylpalladium Intermediates. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1669

    Google Scholar 

  104. Acemoglu L, Williams JMJ (2002) Synthetic Scope of the Tsuji–Trost Reaction with Allylic Halides, Carboxylates, Ethers, and Related Oxygen Nucleophiles as Starting Compounds. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1689

    Google Scholar 

  105. Moreno-Mañas M, Pleixats R (2002) Palladium-Catalyzed Allylation with Allyl Carbonates. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1707

    Google Scholar 

  106. Larock RC, Fried CA (1990) J Am Chem Soc 112:5882

    CAS  Google Scholar 

  107. Takacs JM, Zhu J (1989) J Org Chem 54:5193

    CAS  Google Scholar 

  108. Takacs JM, Zhu J, Chandramouli SV (1992) J Am Chem Soc 114:773

    CAS  Google Scholar 

  109. Takacs JM, Chandramouli SV (1993) J Org Chem 58:7315

    CAS  Google Scholar 

  110. Negishi E, Copéret C, Ma S, Mita T, Sugihara T, Tour JM (1996) J Am Chem Soc 118:5904

    CAS  Google Scholar 

  111. Negishi E, Ma S, Amanfu J, Copéret C, Miller JA, Tour JM (1996) J Am Chem Soc 118:5919

    CAS  Google Scholar 

  112. Copéret C, Negishi E (1999) Org Lett 1:165

    Google Scholar 

  113. Sugihara T, Copéret C, Owczarczvk Z, Harring LS, Negishi E (1994) J Am Chem Soc 116:7923

    CAS  Google Scholar 

  114. Schiller R, Pour M, Fáková H, Kuneš J, Císařová I (2004) J Org Chem 69:6761

    CAS  Google Scholar 

  115. Copéret C, Sugihara T, Negishi E (1995) Tetrahedron Lett 36:1771

    Google Scholar 

  116. Copéret C, Ma S, Sugihara T, Negishi E (1996) Tetrahedron 52:11529

    Google Scholar 

  117. Aggarwal VK, Daries PW, Moss WO (2002) Chem Commun, p 972

    Google Scholar 

  118. Aggarwal VK, Butters M, Daries PW (2003) Chem Commun, p 1046

    Google Scholar 

  119. Aggarwal VK, Daries PW, Schmidt AT (2004) Chem Commun, p 1232

    Google Scholar 

  120. Clique B, Fabritius CH, Couturier C, Monteiro N, Balme G (2003) Chem Commun, p 272

    Google Scholar 

  121. Artman GD III, Weinreb SM (2003) Org Lett 5:1523

    CAS  Google Scholar 

  122. Zhang Y, Wu G, Agnel G, Negishi E (1990) J Am Chem Soc 112:8590

    CAS  Google Scholar 

  123. Dumond YR, Negishi E (2004) Tetrahedron 60:1345. For background information, see pertinent references cited therein

    CAS  Google Scholar 

  124. Negishi E, Harring LS, Owczarczyk Z, Mohamud MM, Ay M (1992) Tetrahedron Lett 33:3253

    CAS  Google Scholar 

  125. Meyer FE, de Meijere A (1991) Synlett, p 777

    Google Scholar 

  126. Negishi E, Ay M, Sugihara T (1993) Tetrahedron 49:5471

    CAS  Google Scholar 

  127. Wang F, Tong X, Cheng J, Zhang Z (2004) Chem Eur J 10:5338

    CAS  Google Scholar 

  128. Huang Q, Larock RC (2003) J Org Chem 68:7342

    CAS  Google Scholar 

  129. Meyer FE, Parsons PJ, de Meijere A (1991) J Org Chem 56:6487

    CAS  Google Scholar 

  130. Henniges H, Meyer FE, Schick U, Funke F, Parsonb PJ, de Meijere A (1996) Tetrahedron 52:11545

    CAS  Google Scholar 

  131. Trost BM, Lee DC (1988) J Am Chem Soc 110:7255

    CAS  Google Scholar 

  132. Trost BM, Shi Y (1991) J Am Chem Soc 113:701

    CAS  Google Scholar 

  133. Wu G, Lamaty F, Negishi E (1989) J Org Chem 54:2507

    CAS  Google Scholar 

  134. Carpenter NE, Kucera DJ, Overman LE (1989) J Org Chem 54:5846

    CAS  Google Scholar 

  135. Grigg R, Sridharan V (1993) Tetrahedron Lett 34:7471

    CAS  Google Scholar 

  136. Overman LE, Ricca DJ, Tran VD (1993) J Am Chem Soc 115:2042

    CAS  Google Scholar 

  137. Overman LE (1994) Pure Appl Chem 66:1423

    CAS  Google Scholar 

  138. Ji J, Lu X (1993) Synlett, p 745

    Google Scholar 

  139. Negishi E, Sawada H, Tour JM, Wei Y (1988) J Org Chem 53:913

    CAS  Google Scholar 

  140. Gagnier SV, Larock RC (2003) J Am Chem Soc 125:4804

    CAS  Google Scholar 

  141. Copéret C, Sugihara T, Wu G, Shimoyama I, Negishi E (1995) J Am Chem Soc 117:3422

    Google Scholar 

  142. Nieman JA, Ennis MD (2000) Org Lett 2:1395

    CAS  Google Scholar 

  143. Nieman JA, Ennis MD (2001) J Org Chem 66:2175

    CAS  Google Scholar 

  144. Negishi E, Wu G, Tour JM (1988) Tetrahedron Lett 29:6745

    CAS  Google Scholar 

  145. Grigg R, Redpath J, Sridharan V, Wilson D (1994) Tetrahedron Lett 35:7661

    CAS  Google Scholar 

  146. Wu G, Shimoyama I, Negishi E (1991) J Org Chem 56:6506

    CAS  Google Scholar 

  147. Kamitani A, Chatani N, Murai S (2003) Angew Chem Int Ed 42:1397

    CAS  Google Scholar 

  148. Oppolzer W, Keller TH, Bedoya-Zurita M, Stone C (1989) Tetrahedron Lett 30:5883

    CAS  Google Scholar 

  149. Oppolzer W (1990) Pure Appl Chem 62:1941

    CAS  Google Scholar 

  150. Yamamoto K, Terakado M, Murai K, Miyazawa M, Tsuji J, Takahashi K, Mikami K (1989) Chem Lett, p 955

    Google Scholar 

  151. Ihle NC, Heathcock CH (1993) J Org Chem 58:560

    CAS  Google Scholar 

  152. Oppolzer W, Xu JZ, Stone C (1991) Helv Chim Acta 74:465

    CAS  Google Scholar 

  153. Oppolzer W, Bienayme H, Genevois-Borella A (1991) J Am Chem Soc 113:9660

    CAS  Google Scholar 

  154. Oppolzer W, Ando A (1992) Chimia 46:122

    CAS  Google Scholar 

  155. Oppolzer W, Robyr C (1994) Tetrahedron 50:415

    CAS  Google Scholar 

  156. Keese R, Guidetti-Grent R, Herzog B (1992) Tetrahedron Lett 33:1207

    CAS  Google Scholar 

  157. Thommen M, Keese R (1997) Synlett, p 231

    Google Scholar 

  158. Copéret C, Ma S, Negishi E (1996) Angew Chem Int Ed 35:2125

    Google Scholar 

  159. Doi T, Yanagisawa A, Yamamoto K, Nakanishi S, Takahashi T (1996) J Org Chem 61:2602

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. H.C. Brown Laboratory of Chemistry, Purdue University, 560 Oval Drive, 47907-2084, West Lafayette, Indiana, USA

    Ei-ichi Negishi, Guangwei Wang & Gangguo Zhu

Authors
  1. Ei-ichi Negishi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Guangwei Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Gangguo Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ei-ichi Negishi .

Editor information

Thomas J. J. Müller

Rights and permissions

Reprints and permissions

About this chapter

Cite this chapter

Negishi, Ei., Wang, G., Zhu, G. Palladium-Catalyzed Cyclization via Carbopalladation and Acylpalladation. 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_013

Download citation

Publish with us

Policies and ethics

Search

Navigation