Abstract
After a short presentation of major variants of nucleophilic substitution of hydrogen, application of these reactions to introduction of substituents into aromatic and heteroaromatic rings and construction of heterocyclic systems are discussed.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Chupakhin ON, Charushin VN, van der Plas HC (1994) Nucleophilic aromatic substitution of hydrogen. Academic Press, San Diego
Terrier F (2013) Modern nucleophilic aromatic substitution. Wiley-VCH, Weinheim
Terrier F (1991) Nucleophilic aromatic displacement. Verlag Chemie, Weinheim
Mąkosza M, Wojciechowski K (2004) Chem Rev 104:2631
Orlov VY, Kotov AD, Rusanov AI (2010) Functionalization of carbo-, N- and O-containing heteroaromatic systems. Mir Publishing Company, Moscow
Mąkosza M, Winiarski J (1987) Acc Chem Res 20:282
Mąkosza M (1996) Russ Chem Bull 45:491
Mąkosza M, Kwast A (1998) J Phys Org Chem 11:341
Mąkosza M (2010) Chem Soc Rev 39:2855
Mąkosza M (2011) Synthesis 2341
Goliński J, Mąkosza M (1978) Tetrahedron Lett 19:3495
Mąkosza M, Goliński J, Baran J (1984) J Org Chem 49:1488
Glinka T, Mąkosza M (1983) J Org Chem 48:3860
Mąkosza M, Ludwiczak S (1984) J Org Chem 49:4562
Mąkosza M, Winiarski J (1984) J Org Chem 49:1494
Stahly GP, Stahly BC, Lilje KC (1984) J Org Chem 49:578
Mudryk B, Mąkosza M (1988) Synthesis 1007
Florio S, Lorusso P, Granito C, Luisi R, Troisi L (2004) J Org Chem 69:4961
Florio S, Lorusso P, Granito C, Ronzini L, Troisi L (2003) Eur J Org Chem 4053
Mąkosza M, Owczarczyk Z (1989) J Org Chem 54:5094
Russell GA, Janzen EG, Strom ET (1964) J Am Chem Soc 86:1807
Bilkis II, Shein SM (1975) Tetrahedron 31:969
Zhang X, Yang D, Liu Y (1993) J Org Chem 58:224
Mąkosza M, Podraza R, Kwast A (1994) J Org Chem 59:6796
Mąkosza M, Glinka T, Kinowski J (1984) Tetrahedron 40:1863
Lemek T, Mąkosza M, Stephenson DS, Mayr H (2003) Angew Chem Int Ed 42:2793
Mąkosza M, Kwast A (2004) Eur J Org Chem 2125
Mąkosza M, Lemek T, Kwast A (1999) Tetrahedron Lett 40:7541
Mąkosza M, Lemek T, Kwast A, Terrier F (2002) J Org Chem 67:394
Błażej S, Mąkosza M (2008) Chem Eur J 14:11113
Seeliger F, Błażej S, Bernhardt S, Mąkosza M, Mayr H (2008) Chem Eur J 14:6108
Miller J (1968) Aromatic nucleophilic substitution. Elsevier, Amsterdam
Mudryk B, Mąkosza M (1988) Tetrahedron 44:209
Mąkosza M, Rydz A, Wróbel Z (1995) Pol J Chem 69:918
Mąkosza M, Kuciak R, Wojciechowski K (1994) Liebigs Ann Chem 615
Mąkosza M, Podraza R (2000) Eur J Org Chem 193
Ostrowski S, Moritz RJ, Mudryk B (1995) Monatsh Chem 126:447
Ostrowski S, Mąkosza M (1989) Liebigs Ann Chem 1989:95
Ostrowski S, Mąkosza M (1989) J Organomet Chem 367:95
Müller P, Bernardinelli G, Motallebi S (1990) Helv Chim Acta 73:1242
Mąkosza M, Sienkiewicz K (1998) J Org Chem 63:4199
Pews RG, Lysenko Z, Vosejpka PC (1997) J Org Chem 62:8255
Angeli A, Angelico F (1901) Gazz Chim Ital 31:27
Katritzky AR, Laurenzo KS (1988) J Org Chem 53:3978
Szpakiewicz B, Grzegożek M (2008) Can J Chem 86:682
Bakke JM, Svensen H, Trevisan R (2001) J Chem Soc Perkin Trans 1:376
Mąkosza M, Białecki M (1998) J Org Chem 63:4878
Parent EE, Dence CS, Sharp TL, Welch MJ, Katzenellenbogen JA (2006) Nucl Med Biol 33:615
Seko S, Miyake K (1998) J Chem Soc Chem Commun 1519
Seko S, Miyake K, Kawamura N (1999) J Chem Soc Perkin Trans 1:1437
Pagoria PF, Mitchell AR, Schmidt RD (1996) J Org Chem 61:2934
Mitchell AR, Coburn MD, Schmidt RD, Pagoria PF, Lee GS (2002) Thermochim Acta 384:205
Rozhkov VV, Shevelev SA, Chervin II, Mitchell AR, Schmidt RD (2003) J Org Chem 68:2498
Mąkosza M, Kwast E (1995) Tetrahedron 51:8339
Kwast E, Mąkosza M (1990) Tetrahedron Lett 31:121
Bernard MK (2000) Tetrahedron 56:7273
Mąkosza M, Chylińska B, Mudryk B (1984) Liebigs Ann Chem 8
Mąkosza M, Sienkiewicz K, Wojciechowski K (1990) Synthesis 850
Andreassen EJ, Bakke JM (2006) J Heterocycl Chem 43:49
Bakke JM (2005) J Heterocycl Chem 42:463
Wojciechowski K, Kosiński S (2001) Tetrahedron 57:5009
Itoh T, Nagata K, Okada M, Ohsawa A (1993) Chem Pharm Bull 41:220
Mąkosza M, Goliński J, Rykowski A (1983) Tetrahedron Lett 24:3277
Charushin VN, Rusinov VL, Chupakhin ON (2008) Compr Heterocycl Chem 9:95
Goliński J, Mąkosza M, Rykowski A (1983) Tetrahedron Lett 24:3279
Mąkosza M, Ostrowski S (1988) J Prakt Chem 330:789
Ostrowicz A, Bałoniak S, Mąkosza M, Rykowski A (1992) Tetrahedron Lett 33:4787
Hamana M, Fujimura Y, Haradahira T (1987) Heterocycles 25:229
Kolesnichenko GA, Malykhin EV, Shteingarts VD (1985) Zh Org Khim 21:1150
van der Plas HC, Woźniak M (1986) Croat Chem Acta 59:33
Szpakiewicz B, Grzegozek M (2004) Russ J Org Chem 40:829
Bartoli G (1984) Acc Chem Res 17:109
Mąkosza M, Surowiec M (2001) J Organomet Chem 624:167
Mąkosza M, Staliński K (1997) Chem Eur J 3:2025
Adam W, Mąkosza M, Staliński K, Zhao C-G (1998) J Org Chem 63:4390
Mąkosza M, Sulikowski D (2009) J Org Chem 74:3827
Mąkosza M, Paszewski M, Sulikowski D (2008) Synlett 2938
Mąkosza M, Sypniewski M (1994) Tetrahedron 50:4913
Mąkosza M, Staliński K (1998) Tetrahedron Lett 39:3575
Davis RB, Pizzini LC (1960) J Org Chem 25:1884
Davis RB, Pizzini LC, Bara EJ (1961) J Org Chem 26:4270
Wróbel Z (2000) Eur J Org Chem 521
Wróbel Z, Stachowska K, Grudzień K, Kwast A (2011) Synlett 1439
Kwast A, Stachowska K, Trawczyński A, Wróbel Z (2011) Tetrahedron Lett 52:6484
Wróbel Z, Kwast A (2010) Synthesis 3865
Wróbel Z, Kwast A (2007) Synlett 1525
Kotsuki H, Kobayashi S, Matsumoto K, Suenaga H, Nishizawa H (1990) Synthesis 1990:1147
Danikiewicz W, Mąkosza M (1991) J Org Chem 56:1283
Mąkosza M, Wojciechowski K (1997) Liebigs Ann/Recueil 1805
Mąkosza M, Wojciechowski K (2001) Heterocycles 54:445
Wróbel Z, Mąkosza M (1990) Org Prep Proced Int 22:575
Mąkosza M, Surowiec M, Voskresensky S (2000) Synthesis 1237
Wojciechowski K (1988) Bull Pol Acad Sci Chem 36:235
Florio S, Lorusso P, Luisi R, Granito C, Ronzini L, Troisi L (2004) Eur J Org Chem 2118
Achmatowicz M, Thiel OR, Gorins G, Goldstein C, Affouard C, Jensen R, Larsen RD (2008) J Org Chem 73:6793
Hartz RA, Ahuja VT, Zhuo X, Mattson RJ, Denhart DJ, Deskus JA, Vrudhula VM, Pan S, Ditta JL, Shu Y-Z, Grace JE, Lentz KA, Lelas S, Li Y-W, Molski TF, Krishnananthan S, Wong H, Qian-Cutrone J, Schartman R, Denton R, Lodge NJ, Zaczek R, Macor JE, Bronson JJ (2009) J Med Chem 52:7653
Leahy DK, Li J, Sausker JB, Zhu J, Fitzgerald MA, Lai C, Buono FG, Braem A, de Mas N, Manaloto Z, Lo E, Merkl W, Su BN, Gao Q, Ng AT, Hartz RA (2010) Org Process Res Dev 14:1221
Prokhorov AM, Mąkosza M, Chupakhin ON (2009) Tetrahedron Lett 50:1444
Leen V, Van der Auweraer M, Boens N, Dehaen W (2011) Org Lett 13:1470
Goumont R, Jan E, Mąkosza M, Terrier F (2003) Org Biomol Chem 1:2192
Mąkosza M, Białecki M (1991) Synlett 181
Tercel M, Lee AE, Hogg A, Anderson RF, Lee HH, Siim BG, Denny WA, Wilson WR (2001) J Med Chem 44:3511
Couch GD, Burke PJ, Knox RJ, Moody CJ (2008) Tetrahedron 64:2816
Avila B, Solano DM, Haddadin MJ, Kurth MJ (2011) Org Lett 13:1060
Ellis D (2011) Synthetic Comm 41:963
Crozet MD, Suspene C, Kaafarani M, Crozet MP, Vanelle P (2004) Heterocycles 63:1629
Pace A, Buscemi S, Vivona N (2007) Org Prep Proced Int 39:1
Pace A, Buscemi S, Vivona N (2005) Org Prep Proced Int 37:447
Surowiec M, Mąkosza M (2004) Tetrahedron 60:5019
Loska R, Majcher M, Mąkosza M (2007) J Org Chem 72:5574
Loska R, Mąkosza M (2007) J Org Chem 72:1354
Crozet MD, Reacutemusat V, Curti C, Vanelle P (2006) Synthetic Comm 36:3639
Mąkosza M, Kwast E (1987) Bull Pol Acad Sci Chem 35:287
Bernard MK, Mąkosza M, Szafran B, Wrzeciono U (1989) Liebigs Ann Chem 1989:545
Wojciechowski K, Mąkosza M (1989) Synthesis 106
Dudzińska-Uzarewicz J, Wrzeciono U, Frankiewicz A, Linkowska E, Kohler T, Nuhn P (1988) Pharmazie 43:611
Bernard MK (1997) Pol J Chem 71:1413
Bernard MK (1995) Pol J Chem 69:1120
Bernard MK, Szoja C, Wrzeciono U (1990) Liebigs Ann Chem 755
Ostrowski S, Wojciechowski K (1990) Can J Chem 68:2239
Mąkosza M, Kinowski A, Danikiewicz W, Mudryk B (1986) Liebigs Ann Chem 69
Ostrowski S, Mikus A (2003) Mol Divers 6:315–321
Ostrowski S, Raczko AM (2005) Helv Chim Acta 88:974
Crozet MD, Botta C, Gasquet M, Curti C, Rémusat V, Hutter S, Chapelle O, Azas N, De Méo M, Vanelle P (2009) Eur J Med Chem 44:653
Mąkosza M, Tyrała A (1987) Synthesis 1142
Crozet MD, Perfetti P, Kaafarani M, Crozet MP, Vanelle P (2004) Lett Org Chem 1:326
Mąkosza M, Glinka T, Ostrowski S, Rykowski A (1987) Chem Lett 61
Katrusiak A (2006) Tetrahedron Lett 47:4259
Wojciechowski K, Modrzejewska H (2003) Synthesis 1503
Rahimizadeh M, Pordel M, Bakavoli M, Eshghi H, Shiri A (2009) Mendeleev Comm 19:161
Mąkosza M, Sulikowski D (2010) Synlett 1666
Mąkosza M, Surowiec M, Szczepańska A, Sulikowski D, Maltsev O (2007) Synlett 470
Sulikowski D, Mąkosza M (2010) Eur J Org Chem 4218
Leen V, Gonzalvo VZ, Deborggraeve WM, Boens N, Dehaen W (2010) Chem Commun 46:4908
Yamada K, Kawasaki T, Fujita T, Somei M (2001) Heterocycles 55:1151
Zhu Z, Sun Z-Y, Ye Y, McKittrick B, Greenlee W, Czarniecki M, Fawzi A, Zhang H, Lachowicz JE (2009) Bioorg Med Chem Lett 19:5218
Rouse MB, Seefeld MA, Leber JD, McNulty KC, Sun L, Miller WH, Zhang S, Minthorn EA, Concha NO, Choudhry AE, Schaber MD, Heerding DA (2009) Bioorg Med Chem Lett 19:1508
Damont A, Boisgard R, Kuhnast B, Lemee F, Raggiri G, Scarf AM, Da Pozzo E, Selleri S, Martini C, Tavitian B, Kassiou M, Dolle F (2011) Bioorg Med Chem Lett 21:4819
Stavenger RA, Cui HF, Dowdell SE, Franz RG, Gaitanopoulos DE, Goodman KB, Hilfiker MA, Ivy RL, Leber JD, Marino JP, Oh HJ, Viet AQ, Xu WW, Ye GS, Zhang DH, Zhao YD, Jolivette LJ, Head MS, Semus SF, Elkins PA, Kirkpatrick RB, Dul E, Khandekar SS, Yi T, Jung DK, Wright LL, Smith GK, Behm DJ, Doe CP, Bentley R, Chen ZX, Hu ED, Lee D (2007) J Med Chem 50:2
Kawakami T, Suzuki H (2000) J Chem Soc Perkin Trans 1:1259
Grzegożek M (2008) J Heterocyclic Chem 45:1879
Grzegożek M, Szpakiewicz B, Kowalski P (2009) Arkivoc 84
Titova IA, Vakul'skaya TI, Larina LI, Mizandrontsev MI, Volkov VA, Dolgushin GV, Lopyrev VA (2005) Russ J Org Chem 41:1306
Vakul’skaya T, Titova I, Larina L, Verkhozina O, Dolgushin G, Lopyrev V (2006) Chem Heterocycl Comp 42:1427
Schmidt RD, Lee GS, Pagoria PF, Mitchell AR, Gilardi R (2001) J Heterocycl Chem 38:1227
Millar RW, Philbin SP, Claridge RP, Hamid J (2004) Propellants Explosives Pyrotechnics 29:81
Bastrakov MA, Starosotnikov AM, Kachala VV, Glukhov IV, Shevelev SA (2009) Russ Chem Bull 58:414
Grzyb S, Ostrowski S (2012) Jordan J Chem 7:231
Ostrowski S, Grzyb S (2012) Tetrahedron Lett 53:6355
Richeter S, Jeandon C, Gisselbrecht JP, Graff R, Ruppert R, Callot HJ (2004) Inorg Chem 43:251
Richeter S, Jeandon C, Gisselbrecht J-P, Ruppert R, Callot HJ (2002) J Am Chem Soc 124:6168
Stefanelli M, Mandoj F, Mastroianni M, Nardis S, Mohite P, Fronczek FR, Smith KM, Kadish KM, Xiao X, Ou ZP, Chen P, Paolesse R (2011) Inorg Chem 50:8281
Verbeeck S, Herrebout WA, Gulevskaya AV, van der Veken BJ, Maes BUW (2010) J Org Chem 75:5126
Gulevskaya AV, Mae BUW, Meyers C, Herrebout WA, van der Veken BJ (2006) Eur J Org Chem 5305
Gulevskaya AV, Maes BUW, Meyers C (2007) Synlett 71
Gulevskaya AV, Verbeeck S, Burov ON, Meyers C, Korbukova IN, Herrebout W, Maes BUW (2009) Eur J Org Chem 2009:564
Borovlev I, Demidov O, Saigakova N, Pisarenko S, Nemykina O (2011) J Heterocycl Chem 48:1206
Demidov OP, Borovlev IV, Pisarenko SV, Nemykina OA, Saigakova NA (2010) Chem Heterocycl Comp 46:636
Bianchi L, Maccagno M, Petrillo G, Sancassan F, Tavani C, Morganti S, Rizzato E, Spinelli D (2007) J Org Chem 72:5771
Patriciu O-I, Pillard C, Finaru A-L, Sandulescu I, Guillaumet G (2007) Synthesis 3868
Grzegożek M, Szpakiewicz B (2006) J Heterocyclic Chem 43:425
Tjosaas F, Fiksdahl A (2007) J Organomet Chem 692:5429
Levinson FS, Varganov RV, Zakiev MM, Shakirova IM, Sheremetev AB, Dmitriev DE, Krivolapov DB, Litvinov IA, Sharafutdinova DR, Efremov YY (2008) Mendeleev Comm 18:329
Millar RW, Claridge RP, Sandall JPB, Thompson C (2002) Arkivoc 19
Claridge RP, Millar RW, Sandall JPB, Thompson C (1999) Tetrahedron 55:10243
Moskalev N, Mąkosza M (1999) Tetrahedron Lett 40:5395
Moskalev N, Barbasiewicz M, Mąkosza M (2004) Tetrahedron 60:347
Sulur M, Sharma P, Ramakrishnan R, Naidu R, Merifield E, Gill DM, Clarke AM, Thomson C, Butters M, Bachu S, Benison CH, Dokka N, Fong ER, Hose DRJ, Howell GP, Mobberley SE, Morton SC, Mullen AK, Rapai J, Tejas B (2012) Org Process Res Dev 16:1746
Timofeev EN, Kolganova NA, Smirnov IP, Kochetkova SV, Florentiev VL (2008) Russian J Bioorg Chem 34:201
Guo W, Miao Z, Sheng C, Yao J, Feng H, Zhang W, Zhu L, Liu W, Cheng P, Zhang J, Che X, Wang W, Luo C, Xu Y (2010) Eur J Med Chem 45:2223
Moskalev N, Mąkosza M (2000) Heterocycles 52:533
Wojciechowski K, Mąkosza M (1984) Tetrahedron Lett 25:4793
Mąkosza M, Paszewski M (2002) Synthesis 2203
Mąkosza M, Hoser H (1994) Heterocycles 37:1701
Walker GN (1955) J Am Chem Soc 77:3844
Mąkosza M, Danikiewicz W, Wojciechowski K (1988) Liebigs Ann Chem 203
Lerman L, Weinstock-Rosin M, Nudelman A (2004) Synthesis 3043
Iakobson G, Posta M, Beier P (2013) Synlett 24:855
Yamagishi H, Matsumoto K, Iwasaki K, Miyazaki T, Yokoshima S, Tokuyama H, Fukuyama T (2008) Org Lett 10:2369
Pedras MSC, Zheng Q-A, Gadagi RS (2007) Chem Commun 4:368
Groszek G, Bednarski M, Dybala M, Filipek B (2009) Eur J Med Chem 44:809
Czeskis BA, Clodfelter DK, Wheeler WJ (2002) J Labelled Compd Rad 45:1143
Mąkosza M, Stalewski J, Maslennikova O (1997) Synthesis 1131
Chackal S, Dudouit F, Houssin R, Hénichart J-P (2003) Heterocycles 60:615
Khdour O, Ouyang A, Skibo EB (2006) J Org Chem 71:5855
Yoshikawa K, Yokomizo A, Naito H, Haginoya N, Kobayashi S, Yoshino T, Nagata T, Mochizuki A, Osanai K, Watanabe K, Kanno H, Ohta T (2009) Bioorg Med Chem 17:8206
Jeanty M, Suzenet F, Guillaumet G (2008) J Org Chem 73:7390
Wróbel Z, Mąkosza M (1993) Synlett 597
Wróbel Z, Mąkosza M (1997) Tetrahedron 53:5501
Stalewski J (1998) Tetrahedron Lett 39:9523
Wróbel Z, Kwast A, Mąkosza M (1993) Synthesis 31
Mąkosza M, Tyrała A (1986) Synthetic Comm 16:419
Söderberg BCG, Banini SR, Turner MR, Minter AR, Arrington AK (2008) Synthesis 903
Banini SR, Turner MR, Cummings MM, Söderberg BCG (2011) Tetrahedron 67:3603
Wróbel Z, Mąkosza M (1993) Tetrahedron 49:5315
Bujok R, Wróbel Z, Wojciechowski K (2012) Synlett 23:1315
Andreassen EJ, Bakke JM, Sletvold I, Svensen H (2004) Org Biomol Chem 2:2671
Lawrence NJ, Davies CA, Gray M (2004) Org Lett 6:4957
Cao S, Wu JJ, Li L, Zhu LJ, Zhang J, Yu JL, Qian XH (2008) Org Biomol Chem 6:1293
Korda A, Wróbel Z (2003) Synlett 1465
Wojciechowski K, Mąkosza M (1986) Synthesis 651
Heffernan GD, Coghlan RD, Manas ES, McDevitt RE, Li Y, Mahaney PE, Robichaud AJ, Huselton C, Alfinito P, Bray JA, Cosmi SA, Johnston GH, Kenney T, Koury E, Winneker RC, Deecher DC, Trybulski EJ (2009) Bioorg Med Chem 17:7802
Bernotas RC, Antane S, Shenoy R, Le V-D, Chen P, Harrison BL, Robichaud AJ, Zhang GM, Smith D, Schechter LE (2010) Bioorg Med Chem Lett 20:1657
Wojciechowski K, Mąkosza M (1986) Bull Soc Chim Belg 95:671
Garrett CE, Prasad K (2004) Adv Synth Catal 346:889
Kawase M, Miyake Y, Sakamoto T, Shimada M, Kikugawa Y (1989) Tetrahedron 45:1653
Bujok R, Kwast A, Cmoch P, Wróbel Z (2010) Tetrahedron 66:698
Bobin M, Kwast A, Wróbel Z (2007) Tetrahedron 63:11048
Wróbel Z (2004) Synlett 1929
Rahimizadeh M, Pordel M, Ranaei M, Bakavoli M (2012) J Heterocycl Chem 49:208
Mąkosza M, Tyrała A (1992) Acta Chem Scand 46:689
Kotovskaya SK, Zhumabaeva GA, Charushin VN, Chupakhin ON (2009) Russ Chem Bull 58:170
Wróbel Z, Wojciechowski K, Kwast A, Gajda N (2010) Synlett 2435
Bujok R, Trawczyński A, Wróbel Z, Wojciechowski K (2012) Synlett 2682
Wojciechowski K (1992) Pol J Chem 66:1121
Wojciechowski K, Mąkosza M (1992) Synthesis 571
Wróbel Z (2001) Tetrahedron 57:7899
Angibaud PR, Venet MG, Filliers W, Broeckx R, Ligny YA, Muller P, Poncelet VS, End DW (2004) Eur J Org Chem 479
Fan XS, Zhang XY, Zhang YM (2005) Heteroatom Chem 16:637
Fan XS, Zhang YM (2002) Tetrahedron Lett 43:7001
Mamo A, Nicoletti S, Tat NC (2002) Molecules 7:618
Kim JL, Kim JK, Hong SI (1999) Polym Bull 42:511
Zhang X, Shetty AS, Jenekhe SA (1998) Acta Polymerica 49:52
Simas ER, Martins TD, Atvars TDZ, Akcelrud L (2009) J Lumin 129:119
Orlov VY, Kotov AD, Ganzha VV, Sokolov VG (2004) Mendeleev Comm 17:37
Orlov VY, Ganzha VV, Kotov AD, Sokolov VG (2007) Russ J Org Chem 43:1502
Rahimizadeh M, Pordel M, Bakavoli M, Bakhtiarpoor Z, Orafaie A (2009) Monatsh Chem 140:633
Sternbach LH (1979) J Med Chem 22:1
Wróbel Z (1997) Synthesis 753
Bakavoli M, Pordel M, Rahimizadeh M, Jahandari P, Seresht ER (2008) Heterocycles 75:165
Wróbel Z, Mąkosza M (1995) Heterocycles 40:187
Sulikowski D, Mąkosza M (2009) Acta Chim Slov 56:680
Wohl A, Aue W (1901) Chem Ber 34:2442
Bujok R, Więcław M, Wróbel Z, Wojciechowski K (2014) Monatsh Chem DOI: 10.1007/S00706-013-1087-3
Wróbel Z, Stachowska K, Kwast A, Gościk A, Królikiewicz M, Pawłowski R, Turska I (2013) Helv Chim Acta 96:956
Królikiewicz M, Cmoch P, Wróbel Z (2013) Synlett 24:973
Takahashi M, Suga D (1998) Synthesis 986
Haydar SN, Yun H, Andrae PM, Mattes J, Zhang J, Kramer A, Smith DL, Huselton C, Graf R, Aschmies S, Schechter LE, Comery TA, Robichaud AJ (2010) J Med Chem 53:2521
Zhou Z, Liu Q-L, Li W, Zhu Y-M (2011) Heterocycles 83:2057
Zhumabaeva GA, Kotovskaya SK, Perova NM, Charushin VN, Chupakhin ON (2006) Russ Chem Bull 55:1243
Esser F, Pook K-H (1992) Synthesis 596
Acknowledgements
This work was supported by grant N204193038 from Ministry of Higher Education and Science.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2013 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Mąkosza, M., Wojciechowski, K. (2013). Nucleophilic Substitution of Hydrogen in Arenes and Heteroarenes. In: Charushin, V., Chupakhin, O. (eds) Metal Free C-H Functionalization of Aromatics. Topics in Heterocyclic Chemistry, vol 37. Springer, Cham. https://doi.org/10.1007/7081_2013_115
Download citation
DOI: https://doi.org/10.1007/7081_2013_115
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-07018-6
Online ISBN: 978-3-319-07019-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)