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Synthesis of Heterocycles via Metal-Catalyzed Reactions that Generate One or More Carbon-Heteroatom Bonds pp 77–107Cite as

Synthesis of Heterocycles via Palladium-Catalyzed Wacker-Type Oxidative Cyclization Reactions of Hydroxy- and Amino-Alkenes

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Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 32))

Abstract

Oxygen and nitrogen containing heterocyclic compounds are some of the most important and prominent structures found in biologically active natural and synthetic products, thus their synthesis is of paramount importance to the chemical community. One particularly important route to the synthesis of these structures is that of Wacker-type oxidative cyclizations. Palladium-catalyzed oxidative cyclizations represent an efficient and simple procedure for the synthesis of a variety of heterocyclic structures. The catalytic system can be fine-tuned to promote different oxidative transformations and to induce asymmetry in to the cyclized products, either via the use of chiral ligands or by manipulating chirality present in the starting substrate.

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Abbreviations

Ac:

Acetyl

Ar:

Aryl

Bn:

Benzyl

Boxax:

Binaphthyl-2,2′-bis(oxazoline)

Bu:

Butyl

dba:

Dibenzylideneacetone

DIPEA:

Diisopropylethylamine

DME:

Dimethoxyethane

DMF:

Dimethylformamide

DMSO:

Dimethyl sulfoxide

equiv:

Equivalent

Et:

Ethyl

h:

Hour(s)

i-Pr:

Isopropyl

Me:

Methyl

MeCN:

Acetonitrile

MeOH:

Methanol

MOA:

Trimethyl orthoacetate

Mol:

Mole

MS:

Molecular sieves

NHC:

N-heterocyclic carbene

Ns:

Nosyl

OAc:

Acetoxy

Ph:

Phenyl

p-Tol:

para-Tolyl

py:

Pyridine

pyrox:

Pyridine-oxazoline

quinox:

2-(4,5-Dihydro-2-oxazolyl)quinoline

rt:

Room temperature

s:

Second(s)

sprix:

Spiro-bis(isoxazoline)

t-Bu:

tert-Butyl

TFA:

Trifluoroacetate

THF:

Tetrahydrofuran

THP:

Tetrahydropyran

Tol:

Toluene

Ts:

Tosyl

References

  1. McDonald RI, Liu G, Stahl SS (2011) Chem Rev 111:2981

    CAS  Google Scholar 

  2. Beccalli EM, Broggini G, Martinelli M, Sottocornola S (2007) Chem Rev 107:5318

    CAS  Google Scholar 

  3. Stahl SS (2004) Angew Chem Int Ed 43:3400

    CAS  Google Scholar 

  4. Backvall JE (1983) Acc Chem Res 16:335

    Google Scholar 

  5. Takacs JM, Jiang X (2003) Curr Org Chem 7:369

    CAS  Google Scholar 

  6. Kotov V, Scarborough CC, Stahl SS (2007) Inorg Chem 46:1910

    CAS  Google Scholar 

  7. Sohn J-H, Waizumi N, Zhong HM, Rawal VH (2005) J Am Chem Soc 127:7290

    CAS  Google Scholar 

  8. Hosokawa T, Hirata M, Murahashi SI, Sonoda A (1976) Tetrahedron Lett 17:1821

    Google Scholar 

  9. Uenishi J, Ohmi M (2005) Angew Chem Int Ed 44:2756

    CAS  Google Scholar 

  10. Van Benthem RATM, Hiemstra H, Speckamp WN (1992) J Org Chem 57:22

    Google Scholar 

  11. Van Benthem RATM, Hiemstra H, Michels JJ, Speckamp WN (1994) J Chem Soc Chem Commun 357

    Google Scholar 

  12. Roenn M, Backvall J, Andersson P (1995) Tetrahedron Lett 36:7749

    CAS  Google Scholar 

  13. Han X, Widenhoefer RA (2004) J Org Chem 69:1738

    CAS  Google Scholar 

  14. Mmutlane EM, Harris JM, Padwa A (2005) J Org Chem 70:8055

    CAS  Google Scholar 

  15. Sharma G, Chander A, Krishnudu K, Krishna P (1998) Tetrahedron Lett 39:6957

    CAS  Google Scholar 

  16. Trend RM, Ramtohul YK, Ferreira EM, Stoltz BM (2003) Angew Chem Int Ed 42:2892

    CAS  Google Scholar 

  17. Trend RM, Ramtohul YK, Stoltz BM (2005) J Am Chem Soc 127:17778

    CAS  Google Scholar 

  18. Hosokawa T, Maeda K, Koga K, Moritani I (1973) Tetrahedron Lett 10:739

    Google Scholar 

  19. Hosokawa T, Ohkata H, Moritani I (1975) Bull Chem Soc Jpn 48:1533

    CAS  Google Scholar 

  20. Hosokawa T, Yamashita S, Murahashi S-I, Sonoda A (1976) Bull Chem Soc Jpn 49:3662

    CAS  Google Scholar 

  21. Muňiz K (2004) Adv Synth Catal 346:1425

    Google Scholar 

  22. Larock R, Wei L, Hightower TR (1998) Synlett 522

    Google Scholar 

  23. Roshchin AI, Kel SM, Bumagin NA (1998) J Organomet Chem 560:163

    CAS  Google Scholar 

  24. Kasahara A, Izumi T, Sato K, Maemura M, Hayasaka T (1977) Bull Chem Soc Jpn 50:1899

    CAS  Google Scholar 

  25. Larock RC, Hightower TR (1993) J Org Chem 58:5298

    CAS  Google Scholar 

  26. Minami T, Nishimoto A, Nakamura Y, Hanaoka M (1994) Bull Chem Soc Jpn 42:1700

    CAS  Google Scholar 

  27. Jabre-Truffert S, Waegell B (1997) Tetrahedron Lett 38:835

    CAS  Google Scholar 

  28. Jacobi PA, Li Y (2003) Org Lett 5:701

    CAS  Google Scholar 

  29. Shoji M, Uno T, Kakeya H, Onose R, Shiina I, Osada H, Hayashi Y (2005) J Org Chem 70: 9905

    CAS  Google Scholar 

  30. He Z, Yudin AK (2006) Org Lett 8:5829

    CAS  Google Scholar 

  31. Arai MA, Kuraishi M, Arai T, Sasai H (2001) J Am Chem Soc 123:2907

    CAS  Google Scholar 

  32. Koranne PS, Tsujihara T, Arai MA, Bajracharya GB, Suzuki T, Onitsuka K, Sasai H (2007) Tetrahedron Asymmetry 18:919

    CAS  Google Scholar 

  33. Takenaka K, Mohanta SC, Patil ML, Rao CVL, Takizawa S, Suzuki T, Sasai H (2010) Org Lett 12:3480

    CAS  Google Scholar 

  34. Reiter M, Ropp S, Gouverneur V (2004) Org Lett 6:91

    CAS  Google Scholar 

  35. Reiter M, Turner H, Mills-Webb R, Gouverneur V (2005) J Org Chem 70:8478

    CAS  Google Scholar 

  36. Hosokawa T, Miyagi S, Murahashi S-I, Sonoda A (1978) J Chem Soc Chem Commun 687

    Google Scholar 

  37. Hosokawa T, Uno T, Murahashi S-I (1979) J Chem Soc Chem Commun 4:475

    Google Scholar 

  38. Hosokawa T, Uno T, Inui S, Murahashi S-I (1981) J Am Chem Soc 103:2318

    CAS  Google Scholar 

  39. Hosokawa T, Okuda C, Murahashi S-I (1985) J Org Chem 50:1282

    CAS  Google Scholar 

  40. Uozumi Y, Kato K, Hayashi T (1997) J Am Chem Soc 119:5063

    CAS  Google Scholar 

  41. Uozumi Y, Kato K, Hayashi T (1998) J Org Chem 63:5071

    CAS  Google Scholar 

  42. Uozumi Y, Kyota H, Kato K, Ogasawara M, Hayashi T (1999) J Org Chem 64:1620

    CAS  Google Scholar 

  43. Zhang YJ, Wang F, Zhang W (2007) J Org Chem 72:9208

    CAS  Google Scholar 

  44. Wang F, Yang G, Zhang YJ, Zhang W (2008) Tetrahedron 64:9413

    CAS  Google Scholar 

  45. Liu Q, Wen K, Zhang Z, Wu Z, Zhang YJ, Zhang W (2012) Tetrahedron 68:5209

    CAS  Google Scholar 

  46. Wang F, Zhang YJ, Wei H, Zhang J, Zhang W (2007) Tetrahedron Lett 48:4083

    CAS  Google Scholar 

  47. Wang F, Zhang YJ, Yang G, Zhang W (2007) Tetrahedron Lett 48:4179

    CAS  Google Scholar 

  48. Semmelhack MF, Epa WR, Cheung W-H, Gu Y, Kim C, Zhang N, Lew W (1994) J Am Chem Soc 116:7455

    CAS  Google Scholar 

  49. Holmes CP, Bartlett PA (1989) J Org Chem 54:98

    CAS  Google Scholar 

  50. Semmelhack MF, Bozell JJ, Sato T, Wulff W, Spiess E, Zask A (1982) J Am Chem Soc 104: 5850

    CAS  Google Scholar 

  51. Semmelhack MF, Zask A (1983) J Am Chem Soc 105:2034

    CAS  Google Scholar 

  52. Tamaru Y (1991) J Org Chem 56:1099

    CAS  Google Scholar 

  53. Boukouvalas J, Fortier G, Radu L-L (1998) J Org Chem 63:916

    CAS  Google Scholar 

  54. Semmelhack MF, Hooley RJ, Kraml CM (2006) Org Lett 8:5203

    CAS  Google Scholar 

  55. Babjak M, Zálupský P, Gracza T (2005) Arkivoc 5:45

    Google Scholar 

  56. Tang Y, Zhang Y, Dai M, Luo T, Deng L, Chen J, Yang Z (2005) Org Lett 7:885

    CAS  Google Scholar 

  57. Tietze LF, Sommer KM, Zinngrebe J, Stecker F (2005) Angew Chem Int Ed 44:257

    CAS  Google Scholar 

  58. Tietze LF, Stecker F, Zinngrebe J, Sommer KM (2006) Chemistry 12:8770

    CAS  Google Scholar 

  59. Tietze LF, Spiegl DA, Stecker F, Major J, Raith C, Grosse C (2008) Chemistry 14:8956

    CAS  Google Scholar 

  60. Kapitán P, Gracza T (2008) Arkivoc 8:8

    Google Scholar 

  61. Evans MA, Morken JP (2005) Org Lett 7:3367

    CAS  Google Scholar 

  62. Minami K, Kawamura Y, Koga K, Hosokawa T (2005) Org Lett 7:5689

    CAS  Google Scholar 

  63. Kawamura Y, Imai T, Hosokawa T (2006) Synlett 3110

    Google Scholar 

  64. Kawamura Y, Kawano Y, Matsuda T, Ishitobi Y, Hosokawa T (2009) J Org Chem 74:3048

    CAS  Google Scholar 

  65. Henry PM (1964) J Am Chem Soc 86:3246

    CAS  Google Scholar 

  66. Keith JA, Henry PM (2009) Angew Chem Int Ed 48:9038

    CAS  Google Scholar 

  67. Comas-Vives A, Stirling A, Lledós A, Ujaque G (2010) Chemistry 16:8738

    CAS  Google Scholar 

  68. James DE, Hines LF, Stille JK (1976) J Am Chem Soc 98:1806

    CAS  Google Scholar 

  69. Majima T, Kurosawa H (1977) J Chem Soc Chem Commun 610

    Google Scholar 

  70. Stille JK, Divakaruni R (1978) J Am Chem Soc 100:1303

    CAS  Google Scholar 

  71. Backvall JE, Akermark B, Ljunggren SO (1979) J Am Chem Soc 101:2411

    Google Scholar 

  72. Zaw K, Henry PM (1990) J Org Chem 55:1842

    CAS  Google Scholar 

  73. Francis JW, Henry PM (1991) Organometallics 10:3498

    CAS  Google Scholar 

  74. Hamed O, Thompson C, Henry PM (1997) J Org Chem 62:7082

    CAS  Google Scholar 

  75. Hayashi T, Yamasaki K, Mimura M, Uozumi Y (2004) J Am Chem Soc 126:3036

    CAS  Google Scholar 

  76. Cornell CN, Sigman MS (2005) J Am Chem Soc 127:2796

    CAS  Google Scholar 

  77. Anderson BJ, Keith JA, Sigman MS (2010) J Am Chem Soc 132:11872

    CAS  Google Scholar 

  78. Hegedus LS, McKearin JM (1982) J Am Chem Soc 104:2444

    CAS  Google Scholar 

  79. Pugin B, Venanzi LM (1983) J Am Chem Soc 105:6877

    CAS  Google Scholar 

  80. Heathcock CH, Stafford JA, Clark DL (1992) J Org Chem 57:2575

    CAS  Google Scholar 

  81. Larock RC, Hightower TR, Hasvold LA, Peterson KP (1996) J Org Chem 61:3584

    CAS  Google Scholar 

  82. Fix SR, Brice JL, Stahl SS (2002) Angew Chem Int Ed 41:164

    CAS  Google Scholar 

  83. Revuelta J, Cicchi S, Brandi A (2005) J Org Chem 70:5636

    CAS  Google Scholar 

  84. Lu Z, Stahl SS (2012) Org Lett 14:1234

    CAS  Google Scholar 

  85. Hegedus LS, Allen GF, Bozell JJ, Waterman EL (1978) J Am Chem Soc 100:5800

    CAS  Google Scholar 

  86. Hegedus LS, Allen G, Olsen D (1980) J Am Chem Soc 102:3583

    CAS  Google Scholar 

  87. Harrington PJ, Hegedus LS (1984) J Org Chem 49:2657

    CAS  Google Scholar 

  88. Beccalli EM, Broggini G, Paladino G, Penoni A, Zoni C (2004) J Org Chem 69:5627

    CAS  Google Scholar 

  89. Zhang Z, Tan J, Wang Z (2008) Org Lett 10:173

    Google Scholar 

  90. Rogers MM, Wendlandt JE, Guzei IA, Stahl SS (2006) Org Lett 8:2257

    CAS  Google Scholar 

  91. Yang G, Zhang W (2012) Org Lett 14:268

    CAS  Google Scholar 

  92. Tsujihara T, Shinohara T, Takenaka K, Takizawa S, Onitsuka K, Hatanaka M, Sasai H (2009) J Org Chem 74:9274

    CAS  Google Scholar 

  93. Mcdonald RI, White PB, Weinstein AB, Tam CP, Stahl SS (2011) Org Lett 13:2830

    CAS  Google Scholar 

  94. Redford JE, Mcdonald RI, Rigsby ML, Wiensch JD, Stahl SS (2012) Org Lett 14:1242

    CAS  Google Scholar 

  95. Scarborough CC, Bergant A, Sazama GT, Guzei IA, Spencer LC, Stahl SS (2009) Tetrahedron 65:5084

    CAS  Google Scholar 

  96. Jiang F, Wu Z, Zhang W (2010) Tetrahedron Lett 51:5124

    CAS  Google Scholar 

  97. Yang G, Shen C, Zhang W (2012) Angew Chem Int Ed 51:9141

    CAS  Google Scholar 

  98. Ham W-H, Hoon Jung Y, Kyunghae L, Oh C-Y, Lee K-Y (1997) Tetrahedron Lett 38:3247

    CAS  Google Scholar 

  99. Oh C-Y, Kim K-S, Ham W-H (1998) Tetrahedron Lett 39:2133

    CAS  Google Scholar 

  100. Szolcsa P, Gracza T, Koman M, Pronayova N, Liptaj T (2000) Tetrahedron Asymmetry 11: 2579

    Google Scholar 

  101. Szolcsányi P, Gracza T, Koman M, Prónayovác N, Liptaj T (2000) Chem Commun 471

    Google Scholar 

  102. Tamaru Y, Hojo M, Higashimura H, Yoshida Z (1988) J Am Chem Soc 110:3994

    CAS  Google Scholar 

  103. Tamaru Y, Hojo M, Yoshida Z (1988) J Org Chem 53:5731

    CAS  Google Scholar 

  104. Harayama H, Takahashi Y, Kimura M, Fugami K, Tanaka S, Tamaru Y (1996) Tetrahedron Lett 37:7287

    CAS  Google Scholar 

  105. Koóš P, Špánik I, Gracza T (2009) Tetrahedron Asymmetry 20:2720

    Google Scholar 

  106. Shinohara T, Arai MA, Wakita K, Arai T, Sasai H (2003) Tetrahedron Lett 44:711

    CAS  Google Scholar 

  107. Harayama H, Abe A, Sakado T, Kimura M, Fugami K, Tanaka S, Tamaru Y (1997) J Org Chem 62:2113

    CAS  Google Scholar 

  108. Yip K-T, Yang M, Law K-L, Zhu N-Y, Yang D (2006) J Am Chem Soc 128:3130

    CAS  Google Scholar 

  109. Yip K, Zhu N, Yang D (2009) Org Lett 11:1911

    CAS  Google Scholar 

  110. He W, Yip K-T, Zhu N-Y, Yang D (2009) Org Lett 11:5626

    CAS  Google Scholar 

  111. Åkermark B, Bäckvall JE, Siiralah K, Sjoberg K, Zetterberg (1974) Tetrahedron Lett 15:1363

    Google Scholar 

  112. Backvall J, Bjorkman EE (1980) J Org Chem 45:2893

    Google Scholar 

  113. Akermark B, Zetterberg K (1984) J Am Chem Soc 106:5560

    Google Scholar 

  114. Backvall J, Bjorkman EE (1984) Acta Chem Scand 8:91

    Google Scholar 

  115. Hegedus LS, Akermark B, Zetterberg K, Olsson LF (1984) J Am Chem Soc 106:7122

    CAS  Google Scholar 

  116. Isomura K, Okada N, Saruwatari M, Yamasaki H, Taniguchi H (1985) Chem Lett 385

    Google Scholar 

  117. Desai LV, Sanford MS (2007) Angew Chem Int Ed 46:5737

    CAS  Google Scholar 

  118. Liu G, Stahl SS (2006) J Am Chem Soc 128:7179

    CAS  Google Scholar 

  119. Mai DN, Wolfe JP (2010) J Am Chem Soc 132:12157

    CAS  Google Scholar 

  120. Brice JL, Harang JE, Timokhin VI, Anastasi NR, Stahl SS (2005) J Am Chem Soc 127:2868

    CAS  Google Scholar 

  121. Hanley PS, Markovic D, Hartwig JF (2010) J Am Chem Soc 132:6302

    CAS  Google Scholar 

  122. Liu G, Stahl SS (2007) J Am Chem Soc 129:6328

    CAS  Google Scholar 

  123. White PB, Stahl SS (2011) J Am Chem Soc 133:18594

    CAS  Google Scholar 

  124. Ye X, Liu G, Popp BV, Stahl SS (2011) J Org Chem 76:1031

    CAS  Google Scholar 

  125. Weinstein AB, Stahl SS (2012) Angew Chem Int Ed 51:11505

    CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, 200240, Shanghai, China

    Nicholas A. Butt & Wanbin Zhang

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  1. Nicholas A. Butt
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  2. Wanbin Zhang
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Correspondence to Wanbin Zhang .

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Editors and Affiliations

  1. Department of Chemistry, University of Michigan, Ann Arbor, Michigan, USA

    John P. Wolfe

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Butt, N.A., Zhang, W. (2013). Synthesis of Heterocycles via Palladium-Catalyzed Wacker-Type Oxidative Cyclization Reactions of Hydroxy- and Amino-Alkenes. In: Wolfe, J. (eds) Synthesis of Heterocycles via Metal-Catalyzed Reactions that Generate One or More Carbon-Heteroatom Bonds. Topics in Heterocyclic Chemistry, vol 32. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2013_102

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