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.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
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
Joule JA (2013) Phosphorus Sulfur Silicon Rel Elem 188:287
Belen’kii LI (2010) Adv Heterocycl Chem 99:143
Forsyth DA, Vogel DE (1979) J Org Chem 44:3971
Carmody MP, Cook MJ, Dassanayake NL, Katritzky AR, Linda P, Tack RD (1976) Tetrahedron 32:1767
Hart H, Sasaoka M (1978) J Am Chem Soc 100:4326
Hogeveen H, Kellog RM, Kuindersma KA (1973) Tetrahedron Lett 40:3929
Koster PB, Janssen MJ (1976) J Chem Soc Perkin Trans 2:323
Belen’kii LI, Suslov IA, Chuvylkin ND (2003) Chem Heterocycl Compd 39:36
Meisel SL, Johnson GC, Hartough HD (1950) J Am Chem Soc 72:1910
Curtis RF, Jones DM, Ferguson G, Hawley DM, Sime JG, Heung KK, Germain G (1969) Chem Commun 165
Yokoyama YU, Yamashita YU, Takahashi K, Sone T (1981) Chem Lett 813
Comey A (1884) Chem Ber 17:790
Minnis W (1932) Org Synth 12:62
Peter A (1884) Chem Ber 17:2643
Biedermann A (1886) Chem Ber 19:636
Stadnikoff G, Goldfarb I (1928) Chem Ber 61:2341
Johnson JR, May GE (1938) Org Synth 18:1
Hartough HD (1952) Thiophene and its derivatives. In: The chemistry of heterocyclic compounds, vol 3. Interscience Publishers, New York
Hartough HD, Meisel SL (1954) Compounds with condensed thiophene rings. In: The chemistry of heterocyclic compounds, vol 7. Interscience Publishers, New York
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
Joule JA, Mills K (2010) Thiophenes: reactions and synthesis. In: Joule JA, Mills K (eds) Heterocyclic chemistry 5th ed. Wiley, New York
Belen’kii LI, Yakubov AP (1984) Tetrahedron 40:2471
Belen’kii Li, Yakubov AP (1986) Tetrahedron 42:759
Belen’kii LI (1992) Chem Heterocycl Compd 28:610
Fürstner A, Voigtländer D, Schrader W, Giebel D, Reetz MT (2001) Org Lett 3:417
Arai S, Sudo Y, Nishida A (2005) Tetrahedron 61:4639
De Noronha RG, Fernandes AC, Romão CC (2009) Tetrahedron Lett 50:1407
Khodaei MM, Bahrami K, Shahbazi F (2008) Chem Lett 37:844
Khodaei MM, Alizadeh A, Nazari E (2007) Tetrahedron Lett 48:4199
Renault O, Dallemagne P, Rault S (1999) Org Prep Proc Int 31:324
Komoto I, Matsuo J, Kobayashi S (2002) Top Catal 19:43
He F, Wu H, Chen J, Su W (2008) Synth Commun 38:255
Su W, Jin C (2004) Synth Commun 34:4249
Barrett AG, Bouloc N, Braddock DC, Chadwick D, Henderson DA (2002) Synlett 1653
Dolbier WR Jr, Cornett E, Martinez H, Xu W (2011) J Org Chem 76:3450
Chavan SP, Garai S, Dutta AK, Pal S (2012) Eur J Org Chem 6841
Nishimoto Y, Babu SA, Yasuda M, Baba A (2008) J Org Chem 73:9465
Katritzky AR, Rachwal S (2010) Chem Rev 110:1564
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
Conde S, Perez DI, Martinez A, Perez C, Moreno FJ (2003) J Med Chem 46:4631
Derdau V, Fey T, Atzrodt J (2010) Tetrahedron 66:1472
Gauvreau D, Dolman SJ, Hughes G, Oshea PD, Davies IW (2010) J Org Chem 75:4078
Shirinyan VZ, Kosterina NV, Kolotaev AV, Belen’kii LI, Krayushkin MM (2000) Chem Heterocycl Comp 36:219
Xiao Y-P, Liu X-Y, Che C-M (2009) J Organomet Chem 694:494
Kantam ML, Aziz K, Likhar PR (2004) Catal Lett 98:117
Stadler D, Bach T (2009) J Org Chem 74:4747
Stadler D, Mühlthau F, Rubenbauer P, Herdtweck E, Bach T (2006) Synlett 2006:2573
Barta J, Pohl R, Klepetarova B, Ernsting NP, Hocek M (2008) J Org Chem 73:3798
Majer J, Kwiatkowski P, Jurczak J (2009) Org Lett 11:4636
Pau A, Murineddu G, Asproni B, Murruzzu C, Grella GE, Pinna GA, Curzu MM, Bagella L, Marchesi I (2009) Molecules 14:3494
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
Abeijon P, Blanco JM, Fernandez F, Garcia M D, Lopez C (2006) Eur J Org Chem 759
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)
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)
Huang Zh, Zhang Ji, Wang N-X (2011) Tetrahedron 67:1788
Sakai N, Asano J, Shimano Y, Konakahara T (2008) Tetrahedron 64:9208
Luo Y, Li C-J (2004) Chem Commun 1930
Andreassen T, Hansen LK, Gautun OR (2008) Eur J Org Chem 4871
Shirakawa S, Berger R, Leighton JL (2005) J Am Chem Soc 127:2858
Esquivias J, Arrayás RG, Carretero JC (2006) Angew Chem Int Ed 45:629
Gol’dfarb YaL, Karmanova IB, Vol’kenshtein YuB, Belen’kii LI (1978) Chem Heterocycl Comp 14:1196
Lucas LN, de Jong JJD, van Esch JH, Kellogg RM, Feringa BL (2003) Eur J Org Chem 155
Neilson BM, Lynch VM, Bielawski ChW (2011) Angew Chem Int Ed 50:10322 (see Supp Inform)
Li Y, Urbas A, Li Q (2012) J Am Chem Soc 134:9573
Goestl R, Kobin B, Grubert L, Paetzel M, Hecht S (2012) Chem Eur J 18:14282
Mrozek T, Goerner H, Daub J (2001) Chem Eur J 7:1028
Liu H-H, Chen Y (2011) J Mater Chem 21:1246
Neilson BM, Bielawski CW (2012) J Am Chem Soc 134:12693
Chen Y, Zeng DX, Fan MG (2003) Org Lett 5:1435
Chen Y, Zeng DX, Xie N, Dang YZ (2005) J Org Chem 70:5001
Traven VF, Bochkov AY, Dolotov SM, Krayushkin MM, Yarovenko VN, Nabatov BV, Barachevsky VA, Beletskaya IP (2008) Org Lett 10:1319
Migulin VA, Krayushkin MM, Barachevsky VA, Kobeleva OI, Valova TM, Lyssenko KA (2012) J Org Chem 77:332
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
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
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
Meyer V, Kreis H (1884) Chem Ber 17:1558
Meyer V, Stadtler O (1885) Chem Ber 18:1488
Weitz L (1884) Chem Ber 17:792
Meyer V, Kreis H (1884) Chem Ber 17:787
Gronowitz S, Hörnfeldt A-B (2004) Synthesis of thiophenes with group VII substituents. In: Thiophenes, Chap 7. Elsevier/Academic, UK
Arsenyan P, Paegle E, Belyakov S (2010) Tetrahedron Lett 51:205
Löb P, Hessel V, Klefenz H, Löwe H, Mazanek K (2005) Lett Org Chem 2:767
Coonradt HL, Hartough HD, Johnson GC (1948) J Am Chem Soc 70:2564
Gronowitz S, Hörnfeldt A-B (2004) Synthesis of thiophenes with group VII substituents. In: Thiophenes, Chap 7. Elsevier/Academic, UK, p 667
Gronowitz S, Hörnfeldt A-B (2004) Synthesis of thiophenes with group VII substituents. In: Thiophenes, Chap 7. Elsevier/Academic, UK, pp 664–668
Okamoto T, Kakinami T, Fujimoto H, Kajigaeshi S (1991) Bull Chem Soc Jpn 64:2566
Muathen HA (1996) Tetrahedron 52:8863
Tanemura K, Suzuki T, Nishida Y, Satsumabayashi K, Horaguchi T (2003) Chem Lett 32:932
Gronowitz S, Hörnfeldt A-B (2004) Synthesis of thiophenes with group VII substituents. In: Thiophenes, Chap 7. Elsevier/Academic, UK, p 682
Kellogg RM, Schaap AP, Harper ET, Wyber H (1968) J Org Chem 33:2902
Raymond F, Di Césare N, Belletête M, Durocher G, Leclerc M (1998) Adv Mater 10:599
Hoflinann KI, Carlsen PHJ (1999) Synth Commun 29:1607
Shaik B, Park JH, An TK, Noh YR, Yoon SB, Park CE, Yoon YJ, Kim Y-H, Lee S-G (2013) Tetrahedron 69:8191
Bäuerle P, Würthner F, Götz G, Effenberger F (1993) Synthesis 1993:1099
Goldberg Y, Alper H (1993) J Org Chem 58:3072
Zhang Y, Tajima K, Hirota K, Hashimoto K (2008) J Am Chem Soc 130:7812
Miyanishi S, Zhang Y, Hashimoto K, Tajima K (2012) Macromolecules 45:6424
Lucas LN, van Esch J, Kellog RM, Feringa BL (1999) Tetrahedron Lett 40:1775
Hermes S, Dassa G, Toso G, Bianco A, Bertarelli C, Zerbi G (2009) Tetrahedron Lett 50:1614
Bhalerao DS, Mahajan US, Akamanchi KG (2008) Synth Commun 38:2814
Muathen HA (2002) Synthesis 169
Muathen HA (1992) J Org Chem 57:2740
Tùng DT, Tuân DT, Pasool N, Villinger A, Reinke H, Fischer C, Langer P (2009) Adv Synth Catal 351:1595
Araki K, Endo H, Masuda G, Ogawa T (2004) Chem Eur J 10:3331
He Y, Wu W, Zhao G, Liu Y, Li Y (2008) Macromolecules 41:9760
Steinkopf W, Jacob H, Penz H (1934) Liebigs Ann Chem 512:136
Gronowitz S (1959) Acta Chem Scand 13:1045
Tietz JI, Seed AJ, Sampson P (2012) Org Lett 14:5058
Gronowitz S, Raznikiewicz T (1964) Org Synth 44:9; (1973) Coll Vol 5:149
Joule JA, Mills K (2010) Thiophenes: reactions and synthesis. In: Joule JA, Mills K (eds) Heterocyclic chemistry 5th ed. Wiley, New York, p 327
Schnürch M (2012) Top Heterocycl Chem 27:185
Hull JW Jr, Romer DR, Podhorez DE, Ash ML, Brady CH (2007) Beilstein J Org Chem 3:1
Krassowska-Świebocka B, Luliński P, Skulski L (1995) Synthesis 926
Sosnowski M, Skulski L (2005) Molecules 10:401
Alexander MA, Khandekar AC, Samant SD (2003) SynLett 1895
Hotta S (2001) J Heterocycl Chem 38:923
Hotta S, Lee SA, Tamaki T (2001) J Heterocycl Chem 37:25
Gronowitz S, Hörnfeldt A-B (2004) Synthesis of thiophenes with group VII substituents. In: Thiophenes, Chap 7. Elsevier/Academic, UK, p 719
Gallo RDC, Ferreira IM, Casagrande GA, Pizzuti L, Oliveira-Silva D, Raminelli C (2012) Tetrahedron Lett 53:5372
De PK, Neckers DC (2012) Org Lett 14:78
D‘Auria M, Distefano C, D’Onofrio F, Mauriello G, Racioppi R (2000) J Chem Soc Perkin Trans 1 3513
D‘Auria M, Mauriello G (1995) Synthesis 248
D‘Auria M, De Mico A, D’Onofrio F, Piancatelli G (1987) J Chem Soc Perkin Trans 1 1777
Meyer V, Stadtler O (1884) Chem Ber 17:2648
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
Babasinian VS (1934) Org Synth 14:76; (1943) Org Synth Col 2:466
Churkin YD, Panfilova LV, Shashkov AS, Burstein KY (1981) Chem Heterocycl Compd 17:232
Churkin YD, Panfilova LV, Lugovoi VD, Boiko NV (1981) Chem Heterocycl Compd 17:673
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
Priestley HM, Hurd CD (1947) J Am Chem Soc 69:1173
Suzuki H, Hidaka I, Osuka A, Iwasa A, Mishina T (1980) Chem Lett 633
Suzuki H, Hidaka I, Iwasa A, Mishina T, Osuka A (1981) Bull Chem Soc Jpn 54:771
Kiyoshi T, Suzuki T, Nishida Y, Satsumabayashi K, Horaguchi T (2003) J Chem Res (S) 497
Tanemura K, Suzuki T, Nishida Y, Satsumabayashi K, Horaguchi T (2001) Chem Lett 2001:1012
Katritzky AR, Scriven EFV, Majumder S, Akhmedova RG, Akhmedov NG, Vakulenko AV (2005) Arkivoc 2005(3):179
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
Aridoss G, Laali KK (2011) J Org Chem 76:8088
King WJ, Nord FF (1948) J Org Chem 13:635
Weston AW, Michaels RJ (1951) Org Synth 31:108, (1963) Org Synth Coll 4:915
Hartmann H (2012) Arkivoc 2012(3):356
Shan WG, Shi XJ, Su WK (2004) Org Prep Proc Int 36:337
Ushijima S, Moriyama K, Togo H (2012) Tetrahedron 68:4588
Steinkopf W, Ohse W (1924) Liebigs Ann Chem 437:14
Meyer V (1883) Chem Ber 16:2968
Meyer V (1884) Chem Ber 17:1563
Langer J (1884) Chem Ber 17:1566
Barange DK, Tu Y-C, Kavala V, Kuo C-W, Yao C-F (2011) Adv Synth Catal 353:41
Mandawad GG, Dawane BS, Beedkar SD, Khobragade CN, Yemul OS (2013) Bioorg Med Chem 21:365
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
Chao J, Taveras AG, Aki CJ (2009) Tetrahedron Lett 50:5005
Hartough HD, Meisel SL (1948) J Am Chem Soc 70:4018
Halfpenny J, Rooney PB, Sloman ZS (2001) J Chem Soc Perkin Trans 1:2595
Ohta M, Quick MP, Yamaguchi J, Wünsch B, Itami K (2009) Chem Asian J 4:1416
Hurd CD, Kreuz KL (1952) J Am Chem Soc 74:2965
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
Consiglio G, Spinelli D, Dell’Erba C, Novi M, Petrillo G (1997) Gazz Chim Ital 127:753
Mąkosza M, Winiarski J (1987) Acc Chem Res 20:282
Mąkosza M, Wojciechowski K (2004) Chem Rev 104:2631
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
Mąkosza M (1991) Synthesis 103
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
Consiglio G, Cosimelli B, Guernelli S, Lanza CZ, Sancassan F, Spinelli D, Stenta M (2010) Eur J Org Chem 5807
Puschmann I, Erker T (1993) Heterocycles 36:1323
Mąkosza M, Sienkiewicz K (1998) J Org Chem 63:4199
Kassmi AL, Heraud G, Buechner W, Fache F, Lemaire M (1992) J Mol Catal 72:299
Mąkosza M, Varvounis G, Surowiec M, Giannopoulo T (2003) Eur J Org Chem 3791
Mąkosza M, Kwast E (1995) Tetrahedron 51:8339
Migaud ME, Wilmouth RC, Mills GI, Wayne GI, Risley C, Chambers C, Macdonald SJF, Schofield CJ (2002) Chem Commun 1274
Mąkosza M, Owczarczyk Z (1989) J Org Chem 54:5094
Wro´bel Z, Makosza M (1992) Pol J Chem 66:2005
Lawrence NJ, Lamarche O, Thurrab N (1999) J Chem Soc Chem Commun 689
Mąkosza M, Staliński K (1998) Synthesis 1631
Ballini R, Bartoli G, Bosco M, Dalpozzo R, Marcantoni E (1988) Tetrahedron 44:6435
Akai SH, Kawashita N, Satoh H, Wada YA, Kakiguchi K, Kuriwaki I, Yasuyuki Kita YA (2004) Org Lett 21:3793
Mąkosza M, Białecki M (1998) J Org Chem 63:4878
Migianu E, Prim D, Kirsch G (2000) Synlett 459
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.
Surange SS, Kumaran G, Rajappa S, Rajalakshmi K, Pattabhi V (1997) Tetrahedron 53:8531
Dell'Erba C, Gabellini A, Novi M, Petrillo G, Tavani C, Cosimelli B, Spinelli D (2001) Tetrahedron 57:8159
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
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
Bianchi L, Maccagno M, Petrillo G, Sancassan F, Tavani C, Morganti S, Rizzato E, Spinelli D (2007) J Org Chem 72:5771
Liang S, Zhang R-Y, Xi L-Y, Chen S-Y, Yu X-Q (2013) J Org Chem 78:11874
Suwiński J, Świerczek K (2001) Tetrahedron 57:1639
Dell'Erba C, Novi M, Guanti G, Sancassan F (1978) J Chem Soc Perkin Trans 1:1140
Dell'Erba C, Novi M, Garbarino G, Petrillo G (1985) J Chem Soc Perkin Trans 2:1741
Dell'Erba C, Novi M, Guanti G, Sancassan F (1976) J Chem Soc Chem Commun 303
Rossi RA, Pierini AB, Peñéñory AB (2003) Chem Rev 103:71
Studer A, Bossart M (2001) In: Renaud P, Sibi MP (eds) Radicals in organic synthesis, vol 2. Wiley-VCH, Weinheim p 62
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
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
Rossi RA (1982) Acc Chem Res 15:164
Maurizio D’Auria (2011) Adv Heterocycl Chem 104:127
Herrera OS, Nieto JD, Olleta AC, Lane SI (2011) J Phys Org Chem 24:398
Belen’kii LI, Gul‘tai VP (1981) Chem Heterocycl Compd 17:523
Joule JA, Mills K (2010) Thiophenes: reactions and synthesis. In: Joule JA, Mills K (eds) Heterocyclic chemistry 5th ed. Wiley, New York, p 333
Shirakawa E, Hayashi T (2012) Chem Lett 41:130
Bowman WR, Storey JMD (2007) Chem Soc Rev 36:1803
Lunazzi L, Placucci G, Grossi L (1982) J Chem Soc Perkin Trans 2:875
Dohi T, Ito M, Morimoto K, Iwata M, Kita Y (2008) Angew Chem Int Ed 47:1301
Zhdankin VV (2009) Arkivoc 2009(1):1
Dohi T, Morimoto K, Kiyono Y, Maruyama A, Tohma H, Kita Y (2005) Chem Commun 2930
Dohi T, Ito M, Sekiguchi S, Ishikado Y, Kita Y (2012) Heterocycles 86:767
Jean A, Cantat J, Bérard D, Bouchu D, Canesi S (2007) Org Lett 9:2553
Budén ME, Guastavino JF, Rossi RA (2013) Org Lett 15:1174
Cogolli P, Maiolo F, Testaferri L, Tiecco M, Tingoli M (1980) J Chem Soc Perkin Trans 2:1331
Bravo A, Bjørsvik H-R, Fontana F, Liguori L, Mele A, Minisci F (1997) J Org Chem 62:7128
Murakami S, Kim S, Isgii H, Fuchigami T (2004) Synlett 815
Baciocchi E, Muraglia E (1993) Tetrahedron Lett 34:5015
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights 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
DOI: https://doi.org/10.1007/7081_2014_134
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-07823-6
Online ISBN: 978-3-319-07824-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)