Skip to main content

Thiophene Substitution Chemistry

  • Chapter
  • First Online:
Thiophenes

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 39))

Abstract

The nucleophilic, electrophilic and radical reactions leading to substitution on a thiophene ring are reviewed. Short historical views are presented where suitable. Recent examples, which in several cases demonstrate the modern application of the method, are presented where possible.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 229.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 299.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Carey FA, Sundberg RJ (2000) Advanced organic chemistry, part a: structure and mechanisms, 4th edn. Kluwer Academic/Plenum, New York/Boston/Dordrecht/London/Moscow, p 569

    Google Scholar 

  2. Joule JA (2013) Phosphorus Sulfur Silicon Rel Elem 188:287

    CAS  Google Scholar 

  3. Belen’kii LI (2010) Adv Heterocycl Chem 99:143

    Google Scholar 

  4. Forsyth DA, Vogel DE (1979) J Org Chem 44:3971

    Google Scholar 

  5. Carmody MP, Cook MJ, Dassanayake NL, Katritzky AR, Linda P, Tack RD (1976) Tetrahedron 32:1767

    CAS  Google Scholar 

  6. Hart H, Sasaoka M (1978) J Am Chem Soc 100:4326

    CAS  Google Scholar 

  7. Hogeveen H, Kellog RM, Kuindersma KA (1973) Tetrahedron Lett 40:3929

    Google Scholar 

  8. Koster PB, Janssen MJ (1976) J Chem Soc Perkin Trans 2:323

    Google Scholar 

  9. Belen’kii LI, Suslov IA, Chuvylkin ND (2003) Chem Heterocycl Compd 39:36

    Google Scholar 

  10. Meisel SL, Johnson GC, Hartough HD (1950) J Am Chem Soc 72:1910

    CAS  Google Scholar 

  11. Curtis RF, Jones DM, Ferguson G, Hawley DM, Sime JG, Heung KK, Germain G (1969) Chem Commun 165

    Google Scholar 

  12. Yokoyama YU, Yamashita YU, Takahashi K, Sone T (1981) Chem Lett 813

    Google Scholar 

  13. Comey A (1884) Chem Ber 17:790

    Google Scholar 

  14. Minnis W (1932) Org Synth 12:62

    Google Scholar 

  15. Peter A (1884) Chem Ber 17:2643

    Google Scholar 

  16. Biedermann A (1886) Chem Ber 19:636

    Google Scholar 

  17. Stadnikoff G, Goldfarb I (1928) Chem Ber 61:2341

    Google Scholar 

  18. Johnson JR, May GE (1938) Org Synth 18:1

    CAS  Google Scholar 

  19. Hartough HD (1952) Thiophene and its derivatives. In: The chemistry of heterocyclic compounds, vol 3. Interscience Publishers, New York

    Google Scholar 

  20. Hartough HD, Meisel SL (1954) Compounds with condensed thiophene rings. In: The chemistry of heterocyclic compounds, vol 7. Interscience Publishers, New York

    Google Scholar 

  21. Taylor R (1985) Electrophilic substitution of thiophene and its derivatives. In: Gronowitz S, Weissberger A, Taylor EC (eds) Thiophene and its derivatives, part 2. The chemistry of heterocyclic compounds, vol 44. Wiley, New York/London/Sydney/Toronto

    Google Scholar 

  22. Joule JA, Mills K (2010) Thiophenes: reactions and synthesis. In: Joule JA, Mills K (eds) Heterocyclic chemistry 5th ed. Wiley, New York

    Google Scholar 

  23. Belen’kii LI, Yakubov AP (1984) Tetrahedron 40:2471

    Google Scholar 

  24. Belen’kii Li, Yakubov AP (1986) Tetrahedron 42:759

    Google Scholar 

  25. Belen’kii LI (1992) Chem Heterocycl Compd 28:610

    Google Scholar 

  26. Fürstner A, Voigtländer D, Schrader W, Giebel D, Reetz MT (2001) Org Lett 3:417

    Google Scholar 

  27. Arai S, Sudo Y, Nishida A (2005) Tetrahedron 61:4639

    CAS  Google Scholar 

  28. De Noronha RG, Fernandes AC, Romão CC (2009) Tetrahedron Lett 50:1407

    Google Scholar 

  29. Khodaei MM, Bahrami K, Shahbazi F (2008) Chem Lett 37:844

    CAS  Google Scholar 

  30. Khodaei MM, Alizadeh A, Nazari E (2007) Tetrahedron Lett 48:4199

    CAS  Google Scholar 

  31. Renault O, Dallemagne P, Rault S (1999) Org Prep Proc Int 31:324

    CAS  Google Scholar 

  32. Komoto I, Matsuo J, Kobayashi S (2002) Top Catal 19:43

    CAS  Google Scholar 

  33. He F, Wu H, Chen J, Su W (2008) Synth Commun 38:255

    CAS  Google Scholar 

  34. Su W, Jin C (2004) Synth Commun 34:4249

    CAS  Google Scholar 

  35. Barrett AG, Bouloc N, Braddock DC, Chadwick D, Henderson DA (2002) Synlett 1653

    Google Scholar 

  36. Dolbier WR Jr, Cornett E, Martinez H, Xu W (2011) J Org Chem 76:3450

    CAS  Google Scholar 

  37. Chavan SP, Garai S, Dutta AK, Pal S (2012) Eur J Org Chem 6841

    Google Scholar 

  38. Nishimoto Y, Babu SA, Yasuda M, Baba A (2008) J Org Chem 73:9465

    CAS  Google Scholar 

  39. Katritzky AR, Rachwal S (2010) Chem Rev 110:1564

    CAS  Google Scholar 

  40. Perez DI, Conde S, Perez C, Gil C, Martinez A, Simon D, Wandosell F, Moreno FJ, Gelpi JL, Luque FJ (2009) Bioorg Med Chem 17:6914

    CAS  Google Scholar 

  41. Conde S, Perez DI, Martinez A, Perez C, Moreno FJ (2003) J Med Chem 46:4631

    CAS  Google Scholar 

  42. Derdau V, Fey T, Atzrodt J (2010) Tetrahedron 66:1472

    CAS  Google Scholar 

  43. Gauvreau D, Dolman SJ, Hughes G, Oshea PD, Davies IW (2010) J Org Chem 75:4078

    CAS  Google Scholar 

  44. Shirinyan VZ, Kosterina NV, Kolotaev AV, Belen’kii LI, Krayushkin MM (2000) Chem Heterocycl Comp 36:219

    CAS  Google Scholar 

  45. Xiao Y-P, Liu X-Y, Che C-M (2009) J Organomet Chem 694:494

    CAS  Google Scholar 

  46. Kantam ML, Aziz K, Likhar PR (2004) Catal Lett 98:117

    Google Scholar 

  47. Stadler D, Bach T (2009) J Org Chem 74:4747

    CAS  Google Scholar 

  48. Stadler D, Mühlthau F, Rubenbauer P, Herdtweck E, Bach T (2006) Synlett 2006:2573

    Google Scholar 

  49. Barta J, Pohl R, Klepetarova B, Ernsting NP, Hocek M (2008) J Org Chem 73:3798

    CAS  Google Scholar 

  50. Majer J, Kwiatkowski P, Jurczak J (2009) Org Lett 11:4636

    CAS  Google Scholar 

  51. Pau A, Murineddu G, Asproni B, Murruzzu C, Grella GE, Pinna GA, Curzu MM, Bagella L, Marchesi I (2009) Molecules 14:3494

    CAS  Google Scholar 

  52. Thurkauf A, Chen X, Zhang S, Gao Y, Kieltyka A, Wasley JWF, Brodbeck R, Greenlee W, Ganguly A, Zhao H (2003) Bioorg Med Chem Lett 13:2921

    CAS  Google Scholar 

  53. Abeijon P, Blanco JM, Fernandez F, Garcia M D, Lopez C (2006) Eur J Org Chem 759

    Google Scholar 

  54. Zhang W, Smith J, Watkins SE, Gysel R, McGehee M, Salleo A, Kirkpatrick J, Ashraf Sh, Anthopoulos Th, Heeney M, McCulloch I. (2010) J Am Chem Soc 132:11437 (see supporting information)

    Google Scholar 

  55. Campiani G, Butini S, Fattorusso C, Trotta F, Gemma S, Catalanotti B, Nacci V, Fiorini I, Cagnotto A, Mereghetti I, Mennini T, Minetti P, Di Cesare MA, Stasi A, Di Serio S, Ghirardi O, Tinti O, Carminati P (2005) J Med Chem 48:1705 (see supporting information)

    Google Scholar 

  56. Huang Zh, Zhang Ji, Wang N-X (2011) Tetrahedron 67:1788

    Google Scholar 

  57. Sakai N, Asano J, Shimano Y, Konakahara T (2008) Tetrahedron 64:9208

    CAS  Google Scholar 

  58. Luo Y, Li C-J (2004) Chem Commun 1930

    Google Scholar 

  59. Andreassen T, Hansen LK, Gautun OR (2008) Eur J Org Chem 4871

    Google Scholar 

  60. Shirakawa S, Berger R, Leighton JL (2005) J Am Chem Soc 127:2858

    CAS  Google Scholar 

  61. Esquivias J, Arrayás RG, Carretero JC (2006) Angew Chem Int Ed 45:629

    CAS  Google Scholar 

  62. Gol’dfarb YaL, Karmanova IB, Vol’kenshtein YuB, Belen’kii LI (1978) Chem Heterocycl Comp 14:1196

    Google Scholar 

  63. Lucas LN, de Jong JJD, van Esch JH, Kellogg RM, Feringa BL (2003) Eur J Org Chem 155

    Google Scholar 

  64. Neilson BM, Lynch VM, Bielawski ChW (2011) Angew Chem Int Ed 50:10322 (see Supp Inform)

    Google Scholar 

  65. Li Y, Urbas A, Li Q (2012) J Am Chem Soc 134:9573

    CAS  Google Scholar 

  66. Goestl R, Kobin B, Grubert L, Paetzel M, Hecht S (2012) Chem Eur J 18:14282

    CAS  Google Scholar 

  67. Mrozek T, Goerner H, Daub J (2001) Chem Eur J 7:1028

    CAS  Google Scholar 

  68. Liu H-H, Chen Y (2011) J Mater Chem 21:1246

    CAS  Google Scholar 

  69. Neilson BM, Bielawski CW (2012) J Am Chem Soc 134:12693

    CAS  Google Scholar 

  70. Chen Y, Zeng DX, Fan MG (2003) Org Lett 5:1435

    CAS  Google Scholar 

  71. Chen Y, Zeng DX, Xie N, Dang YZ (2005) J Org Chem 70:5001

    CAS  Google Scholar 

  72. Traven VF, Bochkov AY, Dolotov SM, Krayushkin MM, Yarovenko VN, Nabatov BV, Barachevsky VA, Beletskaya IP (2008) Org Lett 10:1319

    CAS  Google Scholar 

  73. Migulin VA, Krayushkin MM, Barachevsky VA, Kobeleva OI, Valova TM, Lyssenko KA (2012) J Org Chem 77:332

    CAS  Google Scholar 

  74. Limberakis C (2007) Thiophenes and Benzo[b]thiophenes. In: Li JJ, Gribble GW (eds) Palladium in heterocyclic chemistry: a guide for the synthetic chemist, Chap 5. Elsevier, Oxford/Amsterdam, p 251

    Google Scholar 

  75. Reinecke MG, Padaja P (1986) Halothiophenes and their reactions. In: Gronowitz S, Weissberger A, Taylor EC (eds) Thiophene and its derivatives, part 2. The chemistry of heterocyclic compounds, vol 44, Chap 3. Wiley, New York/London/Sydney/Toronto

    Google Scholar 

  76. Spinelli D, Consiglio G, Dell’Erba C, Novi M (1991) Nucleophilic substitution in thiophene derivatives. In: Gronowitz S, Weissberger A, Taylor EC (eds) Thiophene and its derivatives, part 4. The chemistry of heterocyclic compounds, vol 44, Chap 2. Wiley, New York/London/Sydney/Toronto

    Google Scholar 

  77. Meyer V, Kreis H (1884) Chem Ber 17:1558

    Google Scholar 

  78. Meyer V, Stadtler O (1885) Chem Ber 18:1488

    Google Scholar 

  79. Weitz L (1884) Chem Ber 17:792

    Google Scholar 

  80. Meyer V, Kreis H (1884) Chem Ber 17:787

    Google Scholar 

  81. Gronowitz S, Hörnfeldt A-B (2004) Synthesis of thiophenes with group VII substituents. In: Thiophenes, Chap 7. Elsevier/Academic, UK

    Google Scholar 

  82. Arsenyan P, Paegle E, Belyakov S (2010) Tetrahedron Lett 51:205

    CAS  Google Scholar 

  83. Löb P, Hessel V, Klefenz H, Löwe H, Mazanek K (2005) Lett Org Chem 2:767

    Google Scholar 

  84. Coonradt HL, Hartough HD, Johnson GC (1948) J Am Chem Soc 70:2564

    CAS  Google Scholar 

  85. Gronowitz S, Hörnfeldt A-B (2004) Synthesis of thiophenes with group VII substituents. In: Thiophenes, Chap 7. Elsevier/Academic, UK, p 667

    Google Scholar 

  86. Gronowitz S, Hörnfeldt A-B (2004) Synthesis of thiophenes with group VII substituents. In: Thiophenes, Chap 7. Elsevier/Academic, UK, pp 664–668

    Google Scholar 

  87. Okamoto T, Kakinami T, Fujimoto H, Kajigaeshi S (1991) Bull Chem Soc Jpn 64:2566

    CAS  Google Scholar 

  88. Muathen HA (1996) Tetrahedron 52:8863

    CAS  Google Scholar 

  89. Tanemura K, Suzuki T, Nishida Y, Satsumabayashi K, Horaguchi T (2003) Chem Lett 32:932

    CAS  Google Scholar 

  90. Gronowitz S, Hörnfeldt A-B (2004) Synthesis of thiophenes with group VII substituents. In: Thiophenes, Chap 7. Elsevier/Academic, UK, p 682

    Google Scholar 

  91. Kellogg RM, Schaap AP, Harper ET, Wyber H (1968) J Org Chem 33:2902

    CAS  Google Scholar 

  92. Raymond F, Di Césare N, Belletête M, Durocher G, Leclerc M (1998) Adv Mater 10:599

    CAS  Google Scholar 

  93. Hoflinann KI, Carlsen PHJ (1999) Synth Commun 29:1607

    Google Scholar 

  94. Shaik B, Park JH, An TK, Noh YR, Yoon SB, Park CE, Yoon YJ, Kim Y-H, Lee S-G (2013) Tetrahedron 69:8191

    CAS  Google Scholar 

  95. Bäuerle P, Würthner F, Götz G, Effenberger F (1993) Synthesis 1993:1099

    Google Scholar 

  96. Goldberg Y, Alper H (1993) J Org Chem 58:3072

    CAS  Google Scholar 

  97. Zhang Y, Tajima K, Hirota K, Hashimoto K (2008) J Am Chem Soc 130:7812

    CAS  Google Scholar 

  98. Miyanishi S, Zhang Y, Hashimoto K, Tajima K (2012) Macromolecules 45:6424

    CAS  Google Scholar 

  99. Lucas LN, van Esch J, Kellog RM, Feringa BL (1999) Tetrahedron Lett 40:1775

    CAS  Google Scholar 

  100. Hermes S, Dassa G, Toso G, Bianco A, Bertarelli C, Zerbi G (2009) Tetrahedron Lett 50:1614

    CAS  Google Scholar 

  101. Bhalerao DS, Mahajan US, Akamanchi KG (2008) Synth Commun 38:2814

    CAS  Google Scholar 

  102. Muathen HA (2002) Synthesis 169

    Google Scholar 

  103. Muathen HA (1992) J Org Chem 57:2740

    CAS  Google Scholar 

  104. Tùng DT, Tuân DT, Pasool N, Villinger A, Reinke H, Fischer C, Langer P (2009) Adv Synth Catal 351:1595

    Google Scholar 

  105. Araki K, Endo H, Masuda G, Ogawa T (2004) Chem Eur J 10:3331

    CAS  Google Scholar 

  106. He Y, Wu W, Zhao G, Liu Y, Li Y (2008) Macromolecules 41:9760

    CAS  Google Scholar 

  107. Steinkopf W, Jacob H, Penz H (1934) Liebigs Ann Chem 512:136

    CAS  Google Scholar 

  108. Gronowitz S (1959) Acta Chem Scand 13:1045

    Google Scholar 

  109. Tietz JI, Seed AJ, Sampson P (2012) Org Lett 14:5058

    Google Scholar 

  110. Gronowitz S, Raznikiewicz T (1964) Org Synth 44:9; (1973) Coll Vol 5:149

    Google Scholar 

  111. Joule JA, Mills K (2010) Thiophenes: reactions and synthesis. In: Joule JA, Mills K (eds) Heterocyclic chemistry 5th ed. Wiley, New York, p 327

    Google Scholar 

  112. Schnürch M (2012) Top Heterocycl Chem 27:185

    Google Scholar 

  113. Hull JW Jr, Romer DR, Podhorez DE, Ash ML, Brady CH (2007) Beilstein J Org Chem 3:1

    Google Scholar 

  114. Krassowska-Świebocka B, Luliński P, Skulski L (1995) Synthesis 926

    Google Scholar 

  115. Sosnowski M, Skulski L (2005) Molecules 10:401

    CAS  Google Scholar 

  116. Alexander MA, Khandekar AC, Samant SD (2003) SynLett 1895

    Google Scholar 

  117. Hotta S (2001) J Heterocycl Chem 38:923

    CAS  Google Scholar 

  118. Hotta S, Lee SA, Tamaki T (2001) J Heterocycl Chem 37:25

    Google Scholar 

  119. Gronowitz S, Hörnfeldt A-B (2004) Synthesis of thiophenes with group VII substituents. In: Thiophenes, Chap 7. Elsevier/Academic, UK, p 719

    Google Scholar 

  120. Gallo RDC, Ferreira IM, Casagrande GA, Pizzuti L, Oliveira-Silva D, Raminelli C (2012) Tetrahedron Lett 53:5372

    CAS  Google Scholar 

  121. De PK, Neckers DC (2012) Org Lett 14:78

    CAS  Google Scholar 

  122. D‘Auria M, Distefano C, D’Onofrio F, Mauriello G, Racioppi R (2000) J Chem Soc Perkin Trans 1 3513

    Google Scholar 

  123. D‘Auria M, Mauriello G (1995) Synthesis 248

    Google Scholar 

  124. D‘Auria M, De Mico A, D’Onofrio F, Piancatelli G (1987) J Chem Soc Perkin Trans 1 1777

    Google Scholar 

  125. Meyer V, Stadtler O (1884) Chem Ber 17:2648

    Google Scholar 

  126. Taylor R (1985) Electrophilic substitution of thiophene and its derivatives. In: Gronowitz S, Weissberger A, Taylor EC (eds) Thiophene and its derivatives, part 2. The chemistry of heterocyclic compounds, vol 44. Wiley, New York/London/Sydney/Toronto, p 69

    Google Scholar 

  127. Babasinian VS (1934) Org Synth 14:76; (1943) Org Synth Col 2:466

    Google Scholar 

  128. Churkin YD, Panfilova LV, Shashkov AS, Burstein KY (1981) Chem Heterocycl Compd 17:232

    Google Scholar 

  129. Churkin YD, Panfilova LV, Lugovoi VD, Boiko NV (1981) Chem Heterocycl Compd 17:673

    Google Scholar 

  130. Taylor R (1985) Electrophilic substitution of thiophene and its derivatives. In: Gronowitz S, Weissberger A, Taylor EC (eds) Thiophene and its derivatives, part 2. The chemistry of heterocyclic compounds, vol 44. Wiley, New York/London/Sydney/Toronto, pp 69–74

    Google Scholar 

  131. Priestley HM, Hurd CD (1947) J Am Chem Soc 69:1173

    Google Scholar 

  132. Suzuki H, Hidaka I, Osuka A, Iwasa A, Mishina T (1980) Chem Lett 633

    Google Scholar 

  133. Suzuki H, Hidaka I, Iwasa A, Mishina T, Osuka A (1981) Bull Chem Soc Jpn 54:771

    Google Scholar 

  134. Kiyoshi T, Suzuki T, Nishida Y, Satsumabayashi K, Horaguchi T (2003) J Chem Res (S) 497

    Google Scholar 

  135. Tanemura K, Suzuki T, Nishida Y, Satsumabayashi K, Horaguchi T (2001) Chem Lett 2001:1012

    Google Scholar 

  136. Katritzky AR, Scriven EFV, Majumder S, Akhmedova RG, Akhmedov NG, Vakulenko AV (2005) Arkivoc 2005(3):179

    Google Scholar 

  137. Shackelford SA, Anderson MB, Christie LC, Goetzen T, Guzman MC, Hananel MA, Kornreich WD, Li H, Pathak VP, Rabinovich AK, Rajapakse RJ, Truesdale LK, Tsank SM, Vazir HN (2003) J Org Chem 68:267

    CAS  Google Scholar 

  138. Aridoss G, Laali KK (2011) J Org Chem 76:8088

    CAS  Google Scholar 

  139. King WJ, Nord FF (1948) J Org Chem 13:635

    CAS  Google Scholar 

  140. Weston AW, Michaels RJ (1951) Org Synth 31:108, (1963) Org Synth Coll 4:915

    Google Scholar 

  141. Hartmann H (2012) Arkivoc 2012(3):356

    Google Scholar 

  142. Shan WG, Shi XJ, Su WK (2004) Org Prep Proc Int 36:337

    CAS  Google Scholar 

  143. Ushijima S, Moriyama K, Togo H (2012) Tetrahedron 68:4588

    CAS  Google Scholar 

  144. Steinkopf W, Ohse W (1924) Liebigs Ann Chem 437:14

    CAS  Google Scholar 

  145. Meyer V (1883) Chem Ber 16:2968

    Google Scholar 

  146. Meyer V (1884) Chem Ber 17:1563

    Google Scholar 

  147. Langer J (1884) Chem Ber 17:1566

    Google Scholar 

  148. Barange DK, Tu Y-C, Kavala V, Kuo C-W, Yao C-F (2011) Adv Synth Catal 353:41

    CAS  Google Scholar 

  149. Mandawad GG, Dawane BS, Beedkar SD, Khobragade CN, Yemul OS (2013) Bioorg Med Chem 21:365

    CAS  Google Scholar 

  150. Mader MM, Shih C, Considine E, De Dios A, Grossman CS, Hipskind PA, Lin H-S, Lobb KL, Lopez B, Lopez JE, Cabrejas LMM, Richett ME, White WT, Cheung YY, Huang Z, Reilly JE, Dinn SR (2005) Bioorg Med Chem Lett 15:617

    CAS  Google Scholar 

  151. Chao J, Taveras AG, Aki CJ (2009) Tetrahedron Lett 50:5005

    CAS  Google Scholar 

  152. Hartough HD, Meisel SL (1948) J Am Chem Soc 70:4018

    CAS  Google Scholar 

  153. Halfpenny J, Rooney PB, Sloman ZS (2001) J Chem Soc Perkin Trans 1:2595

    Google Scholar 

  154. Ohta M, Quick MP, Yamaguchi J, Wünsch B, Itami K (2009) Chem Asian J 4:1416

    CAS  Google Scholar 

  155. Hurd CD, Kreuz KL (1952) J Am Chem Soc 74:2965

    CAS  Google Scholar 

  156. Spinelli D, Consiglio G, Dell’Erba C, Novi M (1991) Nucleophilic substitution in thiophene derivatives. In: Gronowitz S (ed) The chemistry of heterocyclic compounds. Thiophene and its derivatives, vol 44, part IV, Chap 2. Wiley, New York, p 295

    Google Scholar 

  157. Consiglio G, Spinelli D, Dell’Erba C, Novi M, Petrillo G (1997) Gazz Chim Ital 127:753

    CAS  Google Scholar 

  158. Mąkosza M, Winiarski J (1987) Acc Chem Res 20:282

    Google Scholar 

  159. Mąkosza M, Wojciechowski K (2004) Chem Rev 104:2631

    Google Scholar 

  160. Paradisi C (1991) Arene substitution via nucleophilic addition to electron deficient arenes. In: Trost B (ed) Fleming I organic synthesis selectivity, strategy and efficiency in modern organic chemistry, vol 4. Pergamon Press, Oxford/New York/Seoul/Tokyo, p 423

    Google Scholar 

  161. Mąkosza M (1991) Synthesis 103

    Google Scholar 

  162. Carey FA, Sundberg RJ (2000) Advanced organic chemistry, part a: structure and mechanisms, 4th edn. Kluwer Academic/Plenum, New York/Boston/Dordrecht/London/Moscow, pp 590, 591

    Google Scholar 

  163. Consiglio G, Cosimelli B, Guernelli S, Lanza CZ, Sancassan F, Spinelli D, Stenta M (2010) Eur J Org Chem 5807

    Google Scholar 

  164. Puschmann I, Erker T (1993) Heterocycles 36:1323

    CAS  Google Scholar 

  165. Mąkosza M, Sienkiewicz K (1998) J Org Chem 63:4199

    Google Scholar 

  166. Kassmi AL, Heraud G, Buechner W, Fache F, Lemaire M (1992) J Mol Catal 72:299

    Google Scholar 

  167. Mąkosza M, Varvounis G, Surowiec M, Giannopoulo T (2003) Eur J Org Chem 3791

    Google Scholar 

  168. Mąkosza M, Kwast E (1995) Tetrahedron 51:8339

    Google Scholar 

  169. Migaud ME, Wilmouth RC, Mills GI, Wayne GI, Risley C, Chambers C, Macdonald SJF, Schofield CJ (2002) Chem Commun 1274

    Google Scholar 

  170. Mąkosza M, Owczarczyk Z (1989) J Org Chem 54:5094

    Google Scholar 

  171. Wro´bel Z, Makosza M (1992) Pol J Chem 66:2005

    Google Scholar 

  172. Lawrence NJ, Lamarche O, Thurrab N (1999) J Chem Soc Chem Commun 689

    Google Scholar 

  173. Mąkosza M, Staliński K (1998) Synthesis 1631

    Google Scholar 

  174. Ballini R, Bartoli G, Bosco M, Dalpozzo R, Marcantoni E (1988) Tetrahedron 44:6435

    CAS  Google Scholar 

  175. Akai SH, Kawashita N, Satoh H, Wada YA, Kakiguchi K, Kuriwaki I, Yasuyuki Kita YA (2004) Org Lett 21:3793

    Google Scholar 

  176. Mąkosza M, Białecki M (1998) J Org Chem 63:4878

    Google Scholar 

  177. Migianu E, Prim D, Kirsch G (2000) Synlett 459

    Google Scholar 

  178. Bianchi L, Maccagno M, Petrillo G, Rizzato E, Sancassan F, Severi E, Spinelli D, Tavani C, Viale M (2007) Versatile nitrobutadienic building-blocks from the ring-opening of 2- and 3-nitrothiophenes. In: Attanasi OA, Spinelli D (eds) Targets in heterocyclic systems: chemistry and properties, vol 11. Soc Chim Ital, Rome, p 1.

    Google Scholar 

  179. Surange SS, Kumaran G, Rajappa S, Rajalakshmi K, Pattabhi V (1997) Tetrahedron 53:8531

    CAS  Google Scholar 

  180. Dell'Erba C, Gabellini A, Novi M, Petrillo G, Tavani C, Cosimelli B, Spinelli D (2001) Tetrahedron 57:8159

    Google Scholar 

  181. Bianchi L, Maccagno M, Petrillo G, Sancassan F, Spinelli D, Tavani C (2006) 2,3-Dinitro-1,3-butadienes: versatile building-blocks from the ring opening of 3,4-dinitrothiophene. In: Attanasi OA, Spinelli D (eds) Targets in heterocyclic systems: chemistry and properties, vol 10. Soc Chim Ital, Rome, p 1

    Google Scholar 

  182. Bianchi L, Dell’Erba C, Maccagno M, Morganti S, Petrillo G, Rizzato E, Sancassan F, Severi E, Spinelli D, Tavani C (2006) Arkivoc 2006(7):169

    Google Scholar 

  183. Bianchi L, Maccagno M, Petrillo G, Sancassan F, Tavani C, Morganti S, Rizzato E, Spinelli D (2007) J Org Chem 72:5771

    CAS  Google Scholar 

  184. Liang S, Zhang R-Y, Xi L-Y, Chen S-Y, Yu X-Q (2013) J Org Chem 78:11874

    CAS  Google Scholar 

  185. Suwiński J, Świerczek K (2001) Tetrahedron 57:1639

    Google Scholar 

  186. Dell'Erba C, Novi M, Guanti G, Sancassan F (1978) J Chem Soc Perkin Trans 1:1140

    Google Scholar 

  187. Dell'Erba C, Novi M, Garbarino G, Petrillo G (1985) J Chem Soc Perkin Trans 2:1741

    Google Scholar 

  188. Dell'Erba C, Novi M, Guanti G, Sancassan F (1976) J Chem Soc Chem Commun 303

    Google Scholar 

  189. Rossi RA, Pierini AB, Peñéñory AB (2003) Chem Rev 103:71

    CAS  Google Scholar 

  190. Studer A, Bossart M (2001) In: Renaud P, Sibi MP (eds) Radicals in organic synthesis, vol 2. Wiley-VCH, Weinheim p 62

    Google Scholar 

  191. Spinelli D, Consiglio G, Dell’Erba C, Novi M (1991) Nucleophilic substitution in thiophene derivatives. In: Gronowitz S (ed) The chemistry of heterocyclic compounds. Thiophene and its derivatives, vol 44, part IV, Chap 2. Wiley, New York, p 372

    Google Scholar 

  192. Porter AEA (1985) Radical reactions of thiophene. In: Gronowitz S (ed) The chemistry of heterocyclic compounds. Thiophene and its derivatives, vol 44, Part 1, Chap IX. Wiley, New York, p 651

    Google Scholar 

  193. Rossi RA (1982) Acc Chem Res 15:164

    CAS  Google Scholar 

  194. Maurizio D’Auria (2011) Adv Heterocycl Chem 104:127

    Google Scholar 

  195. Herrera OS, Nieto JD, Olleta AC, Lane SI (2011) J Phys Org Chem 24:398

    CAS  Google Scholar 

  196. Belen’kii LI, Gul‘tai VP (1981) Chem Heterocycl Compd 17:523

    Google Scholar 

  197. Joule JA, Mills K (2010) Thiophenes: reactions and synthesis. In: Joule JA, Mills K (eds) Heterocyclic chemistry 5th ed. Wiley, New York, p 333

    Google Scholar 

  198. Shirakawa E, Hayashi T (2012) Chem Lett 41:130

    CAS  Google Scholar 

  199. Bowman WR, Storey JMD (2007) Chem Soc Rev 36:1803

    CAS  Google Scholar 

  200. Lunazzi L, Placucci G, Grossi L (1982) J Chem Soc Perkin Trans 2:875

    Google Scholar 

  201. Dohi T, Ito M, Morimoto K, Iwata M, Kita Y (2008) Angew Chem Int Ed 47:1301

    CAS  Google Scholar 

  202. Zhdankin VV (2009) Arkivoc 2009(1):1

    Google Scholar 

  203. Dohi T, Morimoto K, Kiyono Y, Maruyama A, Tohma H, Kita Y (2005) Chem Commun 2930

    Google Scholar 

  204. Dohi T, Ito M, Sekiguchi S, Ishikado Y, Kita Y (2012) Heterocycles 86:767

    CAS  Google Scholar 

  205. Jean A, Cantat J, Bérard D, Bouchu D, Canesi S (2007) Org Lett 9:2553

    CAS  Google Scholar 

  206. Budén ME, Guastavino JF, Rossi RA (2013) Org Lett 15:1174

    Google Scholar 

  207. Cogolli P, Maiolo F, Testaferri L, Tiecco M, Tingoli M (1980) J Chem Soc Perkin Trans 2:1331

    Google Scholar 

  208. Bravo A, Bjørsvik H-R, Fontana F, Liguori L, Mele A, Minisci F (1997) J Org Chem 62:7128

    CAS  Google Scholar 

  209. Murakami S, Kim S, Isgii H, Fuchigami T (2004) Synlett 815

    Google Scholar 

  210. Baciocchi E, Muraglia E (1993) Tetrahedron Lett 34:5015

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Luba Ignatovich .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2014 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Ryabova, V., Ignatovich, L. (2014). Thiophene Substitution Chemistry. In: Joule, J. (eds) Thiophenes. Topics in Heterocyclic Chemistry, vol 39. Springer, Cham. https://doi.org/10.1007/7081_2014_134

Download citation

Publish with us

Policies and ethics