Abstract
This chapter reviews the metallation of thiophenes, the utilization of the resulting organometal species as nucleophiles and as cross-coupling partners, and the cross-coupling reactions of halothiophenes and thiophenes. The main focus lies on transition metal-catalyzed carbon-carbon bond formations.
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References
Russel DK, Press JB (1996) Five-membered rings with one heteroatom and fused carbocyclic derivatives. In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II, vol 2. Oxford, Pergamon, p 680
Schatz J, Brendgen T, Schühle D (2008) Five-membered rings with one heteroatom together with their benzo and other carbocyclic-fused derivatives. In: Katritzky AR, Ramsden CA, Scriven EFV, Taylor RJK (eds) Comprehensive heterocyclic chemistry III, vol 3. Oxford, Elsevier, Amsterdam, p 932
Wang L, He W, Yu Z (2013) Chem Soc Rev 42:599
Grochowski MR, Li T, Brennessel WW, Jones WD (2010) J Am Chem Soc 132:12412
Tan R, Song D (2011) Organometallics 30:1637
Prechtl MHG, Hölscher M, Ben-David Y, Theyssen N, Loschen R, Milstein D, Leitner W (2007) Angew Chem Int Ed 46:2269
Screttas CG (1974) J Chem Soc Perkin Trans 2:745
Screttas CG, Eastham JF (1965) J Am Chem Soc 87:3276
Braun D, Seelig E (1964) Chem Ber 97:3098
Davies GM, Davies PS (1972) Tetrahedron Lett 33:3507
Gilman H, Morton JW Jr (1954) Org React 8:258
Gschwend HW, Rodriguez HR (1979) Org React 26:1
Clarke AJ, McNamara S, Meth-Cohn O (1974) Tetrahedron Lett 15:2373
Ramanathan V, Levine R (1962) J Org Chem 27:1667
Gronowitz S, Cederlund B, Hörnfeldt A-B (1974) Chem Scr 5:217
Acheson RM, MacPhee KE, Philpott PG, Barltrop JA (1956) J Chem Soc 698
Graf R (1963) Justus Liebigs Ann Chem 661:111
Jakobsen HJ, Lawesson S-O (1965) Tetrahedron 21:3331
Gronowitz S (1960) Ark Kemi 16:363
Gronowitz S, Rosen U (1971) Chem Scr 1:33
Gronowitz S, Eriksson B (1963) Ark Kemi 21:335
Slocum DW, Gierer PL (1971) J Chem Soc D Chem Commun 305
Knight DW, Nott AP (1983J) Chem Soc Perkin Trans 1:791
Carpenter JA, Chadwick DJ (1985) Tetrahedron Lett 26:1777
Carpenter AJ, Chadwick DJ (1985) J Org Chem 50:4362
Carpenter AJ, Chadwick DJ (1985) J Chem Soc Perkin Trans 1:173
Shilai M, Kondo Y, Sakamoto T (2001) J Chem Soc Perkin Trans 1:442
Fujiwara Y, Maruyama O, Yoshidomi M, Taniguchi H (1981) J Org Chem 46:851
Zhao J, Huang L, Cheng K, Zhang Y (2009) Tetrahedron Lett 50:2758
Sadykhov ID (1961) Chem Abstr 55:21563e
Maruyama O, Yoshidomi M, Fujiwara Y, Taniguchi H (1979) Chem Lett 8:1229
Mochida S, Hirano K, Satoh T, Miura M (2011) J Org Chem 76:3024
Jie X, Shang Y, Hu P, Su W (2013) Angew Chem Int Ed 52:3630
Roger J, Gottumukkala A, Doucet H (2010) ChemCatChem 2:20
Dong JJ, Doucet H (2010) Eur J Org Chem 2010:611
Mercier LG, Leclerc M (2013) Acc Chem Res 46:1597
Gozzi C, Lavenot L, Ilg K, Penalva V, Lemaire M (1997) Tetrahedron Lett 38:8867
Jeffery T (1996) Tetrahedron 52:10113
Ohta A, Akita Y, Ohkuwa T, Chiba M, Fukunaga R, Miyafuji A, Nakata T, Tani N, Aoyagi Y (1990) Heterocycles 31:1951
Steinmetz M, Ueda K, Grimme S, Yamaguchi J, Kirchberg S, Itami K, Studer A (2012) Chem Asian J 7:1256
Zinovyeva VA, Vorotyntsev MA, Bezverkhyy I, Chaumont D, Hierso J-C (2011) Adv Funct Mater 21:1064
Schipper DJ, Fagnou K (2011) Chem Mater 23:1594
Tamba S, Ide K, Shono K, Sugie A, Mori A (2013) Synlett 24:1133
Tanaka S, Tanaka D, Sugie A, Mori A (2012) Tetrahedron Lett 53:1173
Laidaoui N, Miloudi A, Abed D, Doucet H (2010) Synthesis 2553
Hintermann L, Schmitz M, Chen Y (2010) Adv Synth Catal 352:2411
Liégault B, Petrov I, Gorelsky SI, Fagnou K (2010) J Org Chem 75:1047
He C-Y, Fan S, Zhang X (2010) J Am Chem Soc 132:12850
He C-Y, Min Q-Q, Zhang X (2012) Organometallics 31:1335
Xi P, Yang F, Qin S, Zhao D, Lan J, Gao G, Hu C, You J (2010) J Am Chem Soc 132:1822
Han W, Ofial A (2011) Synlett 1951
Verbitskiy EV, Cheprakova EM, Slepukhin PA, Kodess MI, Ezhikova MA, Pervova MG, Rusinov GL, Chupakhin ON, Charushin VN (2012) Tetrahedron 68:5445
Verbitskiy EV, Cheprakova EM, Zhilina EF, Kodess MI, Ezhikova MA, Pervova MG, Slepukhin PA, Subbotina JO, Schepochkin AV, Rusinov GL, Chupakhin ON, Charushin VN (2013) Tetrahedron 69:5164
Kuhl N, Hopkinson MN, Glorius F (2012) Angew Chem Int Ed 51:8230
Tanaka S, Tamba S, Tanaka D, Sugie A, Mori A (2011) J Am Chem Soc 133:16734
He C-Y, Wang Z, Wu C-Z, Qing F-L, Zhang X (2013) Chem Sci 4:3508
Patrick TB, Willaredt RP, DeGonia DJ (1985) J Org Chem 50:2232
Gomberg M, Bachmann WE (1924) J Am Chem Soc 46:2339
Dermer OC, Edmison MT (1957) Chem Rev 57:77
Bachmann WE, Hoffmann RA (1944) Org React 2:224
Beadle JR, Korzeniowski SH, Rosenberg DE, Garcia-Slanga BJ, Gokel GW (1984) J Org Chem 49:1594
Rosenberg DC, Beadle JR, Korzeniowski SH, Gokel GW (1980) Tetrahedron Lett 21:4141
Nakayama J, Yomoda R, Hoshino M (1987) Heterocycles 26:2215
Buu-Hoi NP, Hoan N (1950) Recl Trav Chim Pays Bas 69:2239
Dohi T, Ito M, Sekiguchi S, Ishikado Y, Kita Y (2012) Heterocycles 86:767
Chotana GA, Kallepalli VA, Maleczka RE, Smith MR (2008) Tetrahedron 64:6103
Pierre C, Baudoin O (2013) Tetrahedron 69:4473
Tappe F, Trepohl V, Oestreich M (2010) Synthesis 3037
Xiang C-B, Bian Y-J, Mao X-R, Huang Z-Z (2012) J Org Chem 77:7706
Dahlmann U, Neidlein R (1996) Helv Chim Acta 79:755
Kang S-K, Kim J-S, Choi S-C (1997) J Org Chem 62:4208
Antolini L, Goldoni F, Iarossi D, Mucci A, Schenetti L (1997) J Chem Soc Perkin Trans 1:1957
Hucke A, Cava MP (1998) J Org Chem 63:7413
Zhang Y, Hömfeldt A-B, Gronowitz S (1995) J Heterocycl Chem 32:435
Zhang Y, Hömfeldt A-B, Gronowitz S (1995) J Heterocycl Chem 32:771
Bao Z, Chan W, Yu L (1993) Chem Mater 5:2
Barbarella G, Zambianchi M (1994) Tetrahedron 50:11249
Barbarella G, Zambianchi M, Sotgiu G, Bongini A (1997) Tetrahedron 53:9401
Groenendaal L, Peerlings HWI, Havinga EE, Vekemans JAJM, Meijer EW (1995) Synth Met 69:467
Bäuerle P, Pfau F, Schlupp H, Würthner F, Gaudl K-U, Caro MB, Fischer P (1993) J Chem Soc Perkin Trans 2:489
Gronowitz S, Peters D (1990) Heterocycles 30:645
Gronowitz S, Zhang Y, Hörnfeldt A-B (1992) Acta Chem Scand 46:654
Pelter A, Jenkins I, Jones DE (1997) Tetrahedron 53:10357
Rossi R, Carpita A, Messeri T (1991) Synth Commun 21:1875
Seitz DE, Lee SH, Hanson RN, Bottaro JC (1983) Synth Commun 13:121
Ye X-S, Yu P, Wong HNC (1997) Liebigs Ann 459
Stanforth SP (1998) Tetrahedron 54:263
Green L, Chauder B, Snieckus V (1999) J Heterocycl Chem 36:1453
Raposo MMM, Fonseca AMC, Kirsch G (2004) Tetrahedron 60:4071
Arnswald M, Neumann WP (1993) J Org Chem 58:7022
Seßler M, Schatz J (2012) Chemie Unserer Zeit 46:48
Scottt WJ, Stille JK (1986) J Am Chem Soc 108:3033
Coulson DR, Satek LC, Grim SO (1972) Inorg Synth 13:121
Schoenberg A, Bartoletti I, Heck RF (1974) J Org Chem 39:3318
Takahashi Y, Ito T, Sakai S, Ishii Y (1970) J Chem Soc D Chem Commun 1065
Dent WT, Long R, Wilkinson AJ (1964) J Chem Soc 1585
Feltham RD, Elbaze G, Ortega R, Eck C, Dubrawski J (1985) Inorg Chem 24:1503
Fitton P, McKeon E, Ream BC (1969) J Chem Soc D Chem Commun 370
Hayashi T, Konishi M, Kobori Y, Kumada M, Higuchi T, Hirotsu K (1984) J Am Chem Soc 106:158
Kharasch MS, Seyler RC, Mayo FR (1938) J Am Chem Soc 60:882
Liebeskind LS, Fengl RW (1990) J Org Chem 55:5359
Liebeskind LS, Pena-Cabrera E (1999) Org Synth 77:135
Farina V (1996) Pure Appl Chem 68:73
Farina V, Kapadia S, Krishnan B, Wang C, Liebeskind LS (1994) J Org Chem 59:5905
Liebeskind S, Wang J (1990) Tetrahedron Lett 31:4293
Rossi R, Carpita A, Ciofalo M, Lippolis V (1991) Tetrahedron 47:8443
Crisp GT (1989) Synth Commun 19:307
Maim J, Björk P, Gronowitz S, Hörnfeldt A-B (1992) Tetrahedron Lett 3:2199
Wang S, Yan S, Hu X, Guo H (1993) Chem Abstr 119:139027
Bumagin NA, Kasatkin AN, Beletskaya IP (1982) Chem Abstr 98:143554
Mitchell TN (1998) In: Diederich F, Stang PJ (eds) Metal-catalyzed cross-coupling reactions. Wiley, Weinheim, 167 p
Farina V, Krishnamurthy V, Scott WJ (1997) Org React 50:1
Furukawa N, Zhang SZ, Sato S, Higaki M (1997) Heterocycles 44:61
Tabet A, Hartmann H (2005) Synthesis 610
Linshoeft J, Heinrich ACJ, Segler SAW, Gates PJ, Staubitz A (2012) Org Lett 14:5644
Gronowitz S, Dahlgren K (1963) Ark Kemi 21:201
Fanta PE (1964) Chem Rev 64:613
Fanta PE (1974) Synthesis 9
Dacons JC, Sitzmann ME (1977) J Heterocycl Chem 14:1151
Zhang S, Zhang D, Liebeskind LS (1997) J Org Chem 62:2312
Nilsson M, Ullenius C (1970) Acta Chem Scand 24:2379
Gjøs N, Gronowitz S (1971) Acta Chem Scand 25:2596
Spargnolo P, Zanirato P, Gronowitz S (1982) J Org Chem 47:3177
Ritter SK, Hill BK, Odian MA, Dai J, Noftle RE, Gard GL (1999) J Fluor Chem 93:73
McLoughlin VCR, Thrower J (1969) Tetrahedron 25:5921
Jabri N, Alexakis A, Normant JF (1981) Tetrahedron Lett 22:3851
Posner GH (1975) Org React 22:253
Lipshutz BH (1992) Org React 41:135
Lipshutz BH, Koerner M, Parker DA (1987) Tetrahedron Lett 28:945
Lipshutz BH (1987) Synthesis 325
Piers E, Tillyer D (1988) J Org Chem 53:5366
Schlegel J, Maas G (2000) J Prakt Chem 342:235
Reinhard R, Glaser M, Neumann R, Maas G (1997) J Org Chem 62:7744
Lipshutz BH (1994) Organocopper-reagents – a practical approach. Oxford University Press, Oxford
Ennis DS, Gilchrist TL (1990) Tetrahedron 46:2623
Rieke RD, Kim S-H, Wu X (1997) J Org Chem 62:6921
Negishi E, Lu F-T, Frisbee R, Matsushita H (1982) Heterocycles 18:117
Negishi E, Xu CD, Tan Z, Kotora M (1997) Heterocycles 46:209
Gronowitz S, Hörnfeldt A-B, Yang Y (1987) Chem Abstr 106:84431j
Gronowitz S, Hörnfeldt A-B, Yang Y (1986) Chem Scr 26:383
Timari G, Hajos G, Riedl Z, Beres M, Soos T, Messmer A, Gronowitz S (1996) Molecules 1:236
Raminelli C, Gargalaka J, Silveira CC, Comasseto JV (2007) Tetrahedron 63:8801
Muschelknautz C, Dostert C, Müller TJJ (2010) Synlett 415
Negishi E-I, Idacavage MJ (1985) Org React 33:1
Frahn J, Schlueter S, Hensel V, Bo Z, Schluter AD (1999) Polym Mater Sci Eng 80:39
Luh T-Y (1996) Rev Heteroaromat Chem 15:61
Gronowitz S, Bobosik V, Lawitz K (1984) Chem Scr 23:120
Suzuki A (1985) Pure Appl Chem 57:1749
Gröger H (2000) J Prakt Chem 342:334
Suzuki A (1999) J Organomet Chem 576:213
Suzuki A (1994) Pure Appl Chem 66:213
Kagan J, Aurora SK (1983) Tetrahedron Lett 24:4043
Malm J, Hörnfeldt A-B, Gronowitz S (1993) Heterocycles 35:245
Gronowitz S (1994) J Heterocycl Chem 31:641
Namtvedt J (1968) Acta Chem Scand 22:1611
Timari G, Messmer A, Gronowitz S (1992) J Heterocycl Chem 29:1049
Gronowitz S, Bugge A (1965) Acta Chem Scand 19:1271
Migliorini A, Oliviero C, Gasperi T, Loreto MA (2012) Molecules 17:4508
Lee C-H, Plunkett KN (2013) Org Lett 15:1202
Briehn CA, Kirschbaum T, Bäuerle P (2000) J Org Chem 65:352
An TK, Jang SH, Kim S-O, Jang J, Hwang J, Cha H, Noh YR, Yoon SB, Yoon YJ, Kim LH, Chung DS, Kwon S-K, Kim Y-H, Lee S-G, Park CE (2013) Chem Eur J 19:14052
Yang G, Xie X, Zhao G, Ding Y (1999) J Fluor Chem 98:159
Solanke P, Bureš F, Pytela O, Kulhánek J, Padělková Z (2013) Synthesis 45:3044
Haddach M, McCarthy JR (1999) Tetrahedron Lett 40:3109
Hark RR, Hauze DB, Petrovskaia O, Joullié MM, Jaouhari R, McComiskey P (1994) Tetrahedron Lett 35:7719
Gronowitz S, Lawitz K (1984) Chem Scr 24:5
Petasis NA, Zavialov IA (1998) J Am Chem Soc 120:11798
Petasis NA, Goodman A, Zavialov IA (1997) Tetrahedron 53:16463
De Bettencourt-Dias A, Viswanathan S, Rollett A (2007) J Am Chem Soc 129:15436
Liu S-J, Zhao Q, Fan Q-L, Huang W (2008) Eur J Inorg Chem 2008:2177
Kondolff I, Doucet H, Santelli M (2005) Synlett 2057
Laurenti D, Feuerstein M, Pèpe G, Doucet H, Santelli M (2001) J Org Chem 66:1633
Gronowitz S, Johnson I, Hörnfeldt A-B (1975) Chem Scr 7:76
Gronowitz S, Moses P, Hakansson R (1960) Ark Kemi 16:267
De Luca G, Martelli G, Spagnolo P, Tiecco M (1970) J Chem Soc C 2504
Decroix B, Morel J, Paulmier C, Pastour P (1972) Bull Soc Chim Fr 1848
Gronowitz S (1955) Ark Kemi 8:87
Gronowitz S, Holm B (1976) Acta Chem Scand B 30:505
Gronowitz S, Vilks V (1963) Ark Kemi 21:191
Hallberg A, Frejd T, Gronowitz S (1978) Chem Scr 13:186
Hallberg A, Gronowitz S (1980) Chem Scr 16:38
Lawesson S-O (1957) Ark Kemi 11:317
Lawesson S-O (1957) Ark Kemi 11:325
Lawesson S-O (1956) Acta Chem Scand 10:1020
Lawesson S-O (1957) Ark Kemi 11:345
Lawesson S-O (1957) Ark Kemi 11:373
Rahman MT, Chilman H (1976) J Ind Chem Soc 53:582
Rosini GP, Jones WD (1992) J Am Chem Soc 114:10767
Shapiro IO, Belen’kii LI, Romanskii IA, Stoyanovich FM, Gol’dfarb YL, Shatenstein AI (1968) Zhur Obshch Khim 38:1998
Wiklund E, Hakansson R (1973) Chem Scr 3:220
Hoshino O, Hirayama T (1997) Heterocycles 44:509
Samanta SS, Ghosh SC, De A (1997) J Chem Soc Perkin Trans 1:2683
Konstantinov PA, Shupik RI (1963) Zhur Obshch Khim 33:1251
Andrey O, Glanzmann C, Landais Y, Parra-Rapado L (1997) Tetrahedron 53:2835
Gronowitz S, Hörnfeldt A-B, Lukevics E, Pudova O (1994) Synthesis 40
Fröhlich H, Kalt W (1990) J Org Chem 55:2993
Furukawa N, Hoshiai H, Shibutani T, Higaki M, Iwasaki F, Fujihara M (1992) Heterocycles 34:1085
Goldberg Y, Sturkovich R, Lukevics E (1993) Synth Commun 23:1235
Thames SF, Edwards LH, Jacobs TN, Grube PL, Pinkerton FH (1972) J Heterocycl Chem 9:1259
Thames SF, McCleskey JE (1967) J Heterocycl Chem 4:146
Denat F, Gaspard-Iloghmane H, Dubac J (1992) Synthesis 954
Van Pham C, Macomber RS, Mark HB Jr, Zimmer H (1984) J Org Chem 49:5250
Gol’dfarb YL, Kalik MA, Shult’s NA, Belen’kii LI (1979) Chem Abstr 91:140655
Cymerman Craig J, Moyle M (1963) J Chem Soc 3907
Cruceyra A, Gomez-Parra V, Madronero R (1977) Chem Abstr 87:201452
Gronowitz S, Skramstad JE, Eriksson B (1967) Ark Kemi 28:99
Pirson P, Schonne A, Christiaens L (1979) Bull Soc Chim Belg 79:575
Fischer O, Müller A, Vilsmeier A (1925) J Prakt Chem 109:69
Jones G, Stanforth SP (1997) Org React 49:1
Sicé J (1954) J Org Chem 19:70
Gronowitz S (1955) Ark Kemi 8:441
Sukiasyan AN, Litvinov VP, Gol’dfarb YL (1970) Izv Akad Nauk Seriya Khimicheskaya 1345
Gronowitz S, Moses P, Hörnfeldt A-B, Hakansson R (1961) Ark Kemi 17:165
Wiersema A, Gronowitz S (1970) Acta Chem Scand 24:2593
Poirier Y, Legrand L, Lozac’h N (1966) Bull Soc Chim Fr 1054
Yom-Tov B, Gronowitz S (1973) Chem Scr 3:165
Detty MR, Hays DS (1995) Heterocycles 40:925
Gol’dfarb YL, Vol’kenshtein YB, Lopatin BV (1964) Zhur Obshch Khim 34:969
Gol’dfarb YL, Kalik MA, Kirmalova ML (1962) Izv Akad Nauk Seriya Khimicheskaya 701
Carroll WA, Zhang X (1997) Tetrahedron Lett 38:2637
MacDowell DWH, Jeffries AT (1971) J Org Chem 36:1053
Selnick HG, Radzilowski EM, Ponticello GS (1991) Tetrahedron Lett 32:721
Gronowitz S (1958) Ark Kemi 12:533
Fikentscher R, Briickmann R, Betz R (1990) Liebigs Ann 113
DiMenna WS (1980) Tetrahedron Lett 21:2129
Pinkerton FH, Thames SF (1972) J Heterocycl Chem 9:725
Van Zyl G, Langenberg RJ, Tan HH, Schut RN (1956) J Am Chem Soc 78:1955
Katritzky AR, Zhang Z, Lang H, Jubran N, Leichter LM, Sweeny N (1997) J Heterocycl Chem 34:561
Slocum DW, Gierer PL (1976) J Org Chem 41:3668
Katritzky AR, Wang J, Yang B (1995) Synth Commun 25:2631
Hallberg A, Gronowitz S (1980) Chem Scr 16:42
Starostina TA, Paleeva IE, Kozhemyakina LF, Rybakova LF, Shifrina RR, Chernoplekova VA, Kocheshkov KA (1978) Zhur Org Khim 12:2600
Sauvêtre R, Normant JF (1982) Tetrahedron Lett 23:4325
Kooyman JGA, Hendriks HPG, Montijn PP, Brandsma L, Arens JF (1968) Recl Trav Chim Pays Bas 87:69
Katritzky AR, Serdyuk L, Xie L, Ghiviriga I (1997) J Org Chem 62:6215
Takeshita M, Tashiro M (1992) J Org Chem 57:746
Takeshita M, Koike M, Tsuzuki H, Tashiro M (1992) J Org Chem 57:4654
Schuetz RD, Taft DD, O’Brien JP, Shea JL, Mork HM (1963) J Org Chem 28:1420
Christiansen H, Gronowitz S, Rodnar B, Rodnar S, Rosen U, Sharma MK (1969) Ark Kemi 30:561
Gronowitz S, Svenson R, Bondesson G, Magnusson O, Stjernström NE (1974) Acta Pharm Suec 11:211
Almquist A, Hakansson R (1977) Chem Scr 11:57
Gronowitz S, Dahlgren F, Namtvedt J, Roos C, Rosen C, Sjöberg B, Forsgren U (1971) Acta Pharm Suec 8:623
Gronowitz S, Frejd T (1975) Acta Chem Scand B 29:818
Gronowitz S, Holm B (1977) J Heterocycl Chem 14:281
Consiglio G, Spinelli D, Gronowitz S, Hörnfeldt A-B, Maltesson B (1982) J Chem Soc Perkin Trans 2:625
Takahashi K, Tarutani S (1996) Heterocycles 43:1927
Wu X, Chen T-A, Zhu L, Rieke RD (1994) Tetrahedron Lett 35:3673
Gronowitz S, Dahlgren T (1977) Chem Scr 12:57
Gronowitz S, Frejd T (1976) Acta Chem Scand B 30:485
Gronowitz S, Hakansson R (1960) Ark Kemi 16:309
Gol’dfarb YL, Kalik MA, Kirmalova ML (1962) Zhur Obshch Khim 32:222
Jones E, Moodie IM (1970) Org Synth 50:104
Jakobsen HJ, Larsen EH, Lawesson S-O (1963) Tetrahedron 19:1867
Baarschers WH (1976) Can J Chem 54:3056
Walford GL, Shen TY, Witzel BE (Merck and Co. Inc), Fr 2053009 (1972) Chem Abstr 76:113053g
Girodier LD, Maignan CS, Rouessac FP (1995) Tetrahedron Asymmetry 6:2045
Kalinin VN (1992) Synthesis 413
Wu X, Rieke RD (1995) J Org Chem 60:6658
Shi W, Liu C, Lei A (2011) Chem Soc Rev 40:2761
Vechorkin O, Proust V, Hu X (2009) J Am Chem Soc 131:9756
López-Pérez A, Adrio J, Carretero JC (2009) Org Lett 11:5514
Huddleston NE, Sontag SK, Bilbrey JA, Sheppard GR, Locklin J (2012) Macromol Rapid Commun 33:2115
Sharf VZ, Belen’kii LI, Gurovets AS, Karmanoval B (1982) Chem Abstr 96:181087
Sharf VZ, Taits SZ, Gurovets AS, Vol’kenshtein YB, Fabrichnyi BP, Shcherbakova SI (1982) Chem Abstr 96:181086
Mozingo R, Harris SA, Arth GE, Folkers K (Merck & Co. I.) (1950) Chem Abstr 44:2565
Hromatka O, Binder D, Pixner G (1973) Monatsh Chem 104:1348
Mozingo R, Harris SA, Wolf DE, Hoffhine CE, Easton NR, Folkers K (1945) J Am Chem Soc 67:2092
Hromatka O, Binder D, Pixner G (1975) Monatsh Chem 106:1103
Bak B (1956) J Org Chem 21:797
Bak B, Christensen D, Rastrup-Andersen J, Tannenbaum E (1956) J Chem Phys 25:892
Gronowitz S (1959) Acta Chem Scand 13:1045
Gronowitz S, Raznikiewicz T (1964) Org Synth 44:9
Gupta BD, Roy S (1984) Tetrahedron Lett 25:3255
Hallberg A, Lilljefors S, Pedaja P (1981) Synth Commun 11:25
Kellogg RM, Wynberg H (1967) J Am Chem Soc 89:3495
Lunazzi L, Mangini A, Placucci G, Spagnolo P, Tiecco M (1972) J Chem Soc Perkin Trans 2:192
Němec M, Janda M, Šrogl J, Stibor I (1974) Coll Czech Chem Commun 39:3527
Profft E, Solf G (1964) J Prakt Chem 24:38
Schuetz RD, Gruen FM, Byrne DR, Brennan RL (1966) J Heterocycl Chem 3:184
Sone T, Abe Y, Oikawa T (1972) Chem Abstr 76:153468
Gol’dfarb YL, Litvinov VP, Ozolin SA (1965) Chem Abstr 63:592
Hoffmann RA, Gronowitz S (1959) Ark Kemi 15:45
Buzas A, Teste J (1960) Bull Soc Chim Fr 793
Langer J (1884) Ber Dtsch Chem Gesell 17:1566
Profft E, Mitternacht H (1962) J Prakt Chem 16:13
(Consortium für Elektrochemische Industrie GmbH), FR 1 568529 (1970) Chem Abstr 72:100490
Mack W (1967) Angew Chem Int Ed Engl 6:1083
Arnold DR, Hadjiantoniou CP (1978) Can J Chem 56:1970
Fabrichnyi BP, Shalavina IF, Zurabyan SE, Gol’dfarb YL, Kostrova SM (1968) Chem Abstr 69:18565
Motoyama R, Nishimura S, Imoto E, Murakami Y, Hari K, Ogawa J (1960) Chem Abstr 54:14223
Nishimura S, Motoyama R, Imoto E (1959) Chem Abstr 53:4248
Peeters LD, Jacobs SG, Eevers W, Geise HJ (1994) Tetrahedron 50:11533
Bastian JM, Ebnöther A, Jucker E, Rissi E, Stoll AP (1971) Helv Chim Acta 54:277
Blatt AH, Bach S, Kresch LW (1957) J Org Chem 22:1693
Imoto E, Otsuji Y (1959) Chem Abstr 53:3027
King WJ, Nord FF (1949) J Org Chem 14:638
Tilak BD, Malte AM (1969) Indian J Chem 7:1175
Blatt AH, Gross N, Tristram EW (1957) J Org Chem 22:1588
Buu-Hoï NP, Hoán N, Xuong ND (1952) Recl Trav Chim Pays Bas 71:285
Kellogg RM, Schaap AP, Harper ET, Wynberg H (1968) J Org Chem 33:2902
Gjos N, Gronowitz S (1967) Acta Chem Scand 21:2893
Gronowitz S, Raznikiewicz T (1973) Org Synth Coll Vol 5:149
Xie Y, Ng SC, Hor TSA, Chan HSO (1996) J Chem Res 150
Iranpoor N, Firouzabadi H, Azadi R (2008) J Organomet Chem 693:2469
Cellier PP, Spindler J-F, Taillefer M, Cristau H-J (2003) Tetrahedron Lett 44:7191
Jones RG, Gilman H (1951) Org React 6:339
Gronowitz S, Cederlund B, Hörnfeldt A-B (1974) Chem Abstr 81:49013
Kano S, Yuasa Y, Yokomatsu F, Shibuya S (1983) Heterocycles 20:2035
Karlsson JO, Gronowitz S, Frejd T (1982) J Org Chem 47:374
Gronowitz S, Rosen U (1971) Chem Abstr 75:20080
Gjos N, Gronowitz S (1972) Acta Chem Scand 26:1851
Gronowitz S, Frejd T, Karlsson O, Lawitz K, Pedaja P, Pettersson K (1981) Chem Scr 18:192
Karlsson JO, Svensson A, Gronowitz S (1984) J Org Chem 49:2018
Kellogg RM, Buter J (1971) J Org Chem 36:2236
Taylor EC, Vogel DE (1985) J Org Chem 50:1002
Nilsson M, Ullenius C (1971) Acta Chem Scand 25:2428
Smith MR Jr, Gilman H (1972) J Organomet Chem 42:1
Haiduc I, Gilman H (1971) Chem Abstr 75:36230
Smith MR Jr, Gilman H (1971) Organomet Chem Synth 1:265
Gronowitz S, Hallberg A, Glennow C (1980) J Heterocycl Chem 17:171
Janda M, Šrogl J, Stibor I, Nêmec M, Vopatrná P (1972) Synthesis 545
Kraak A, Wiersema AK, Jordens P, Wynberg H (1968) Tetrahedron 24:3381
Frejd T (1977) J Heterocycl Chem 14:1085
Frejd T, Karlsson O, Gronowitz S (1981) J Org Chem 46:3132
Gronowitz S, Frejd T (1970) Acta Chem Scand 24:2656
Gronowitz S, Frejd T (1976) Acta Chem Scand B 30:287
Gronowitz S, Hagen S (1967) Ark Kemi 27:153
Karlsson O, Gronowitz S, Hallberg A (1982) Chem Scr 20:37
Gronowitz S, Pettersson K (1976) J Heterocycl Chem 13:1099
Lawesson S-O (1957) Ark Kemi 11:337
Peters AT, Walker D (1957) J Chem Soc 1525
Heck RF (1982) Org React 27:345
Herrmann WA, Reisinger C-P (1998) Aqueous-phase organometallic catalysis, concepts and applications, Weinheim, Wiley, 382
Hirao T, Enda J, Ohshiro Y, Agawa T (1981) Chem Lett 10:403
Frank WC, Kim YC, Heck RF (1978) J Org Chem 43:2947
Shi G, Huang X, Hong F (1996) J Chem Soc Perkin Trans 1:763
Polshettiwar V, Hesemann P, Moreau JJE (2007) Tetrahedron 63:6784
Oberholzer M, Gerber R, Frech CM (2012) Adv Synth Catal 354:627
Martínez MM, Peña-López M, Sestelo JP, Sarandeses LA (2012) Org Biomol Chem 10:3892
Pei W, Mo J, Xiao J (2005) J Organomet Chem 690:3546
Berthiol F, Kondolff I, Doucet H, Santelli M (2004) J Organomet Chem 689:2786
Bolzoni A, Viglianti L, Bossi A, Mussini PR, Cauteruccio S, Baldoli C, Licandro E (2013) Eur J Org Chem 2013:7489
Kim S-H, Rieke RD (1997) Tetrahedron Lett 38:993
Kim S-H, Hanson MV, Rieke RD (1996) Tetrahedron Lett 37:2197
Gosmini C, Nédélec JY, Périchon J (1997) Tetrahedron Lett 38:1941
Livi F, CarlÕ JE, Bundgaard E (2014) Thiophene in conducting polymers: synthesis of poly(thiophene)s and other conjugated polymers containing thiophenes, for application in polymer solar cells. Top Heterocycl Chem. doi:10.1007/7081_2014_128
He G, Kang L, Delgado WT, Shynkaruk O, Ferguson MJ, McDonald R, Rivard E (2013) J Am Chem Soc 135:5360
Tùng ĐT, Tuân ĐT, Rasool N, Villinger A, Reinke H, Fischer C, Langer P (2009) Adv Synth Catal 351:1595
Billingsley K, Buchwald SL (2007) J Am Chem Soc 129:3358
Toguem S-M, Villinger A, Langer P (2009) Synlett 3311
Toguem S-M, Villinger A, Langer P (2010) Synlett 909
Min J, Wang P, Srinivasan S, Nwachukwu JC, Guo P, Huang M, Carlson KE, Katzenellenbogen JA, Nettles KW, Zhou H-B (2013) J Med Chem 56:3346
Varello S, Handy S (2008) Synthesis 138
Yamamoto Y, Takizawa M, Yu X-Q, Miyaura N (2008) Angew Chem Int Ed Engl 47:928
Wang J, Seefeld MA, Luengo J (2011) Tetrahedron Lett 52:6346
Sévigny S, Forgione P (2013) New J Chem 37:589
Lee D-H, Taher A, Ahn W-S, Jin M-J (2010) Chem Commun 46:478
Van den Hoven BG, Alper H (1999) J Org Chem 64:9640
Bumagin NA, Sukhomlinova L, Luzikova EV, Tolstaya TP, Beletskaya IP (1996) Tetrahedron Lett 37:897
Rossi R, Carpita A, Lezzi A (1984) Tetrahedron 40:2773
Arsenyan P, Rubina K, Vasiljeva J, Belyakov S (2013) Tetrahedron Lett 54:6524
Seidler A, Svoboda J, Dekoj V, Chocholoušová JV, Vacek J, Stará IG, Stary I (2013) Tetrahedron Lett 54:2795
Dieck HA, Heck RF (1975) J Organomet Chem 93:259
Schmid S, Mishra A, Bäuerle P (2011) Chem Commun 47:1324
Prampolini G, Bellina F, Biczysko M, Cappelli C, Carta L, Lessi M, Pucci A, Ruggeri G, Barone V (2013) Chem Eur J 19:1996
Leu WCW, Fritz AE, Digianantonio KM, Hartley CS (2012) J Org Chem 77:2285
Gronowitz S, Lawitz K (1983) Chem Scr 22:265
Chia L-Y, McWhinnie WR (1980) J Organomet Chem 188:121
D’Auria M (1994) Gazz Chim Ital 124:195
Torborg C, Zapf A, Beller M (2008) ChemSusChem 1:91
Raju S, Kumar PR, Mukkanti K, Annamalai P, Pal M (2006) Bioorg Med Chem Lett 16:6185
Nandurkar NS, Bhanage BM (2008) Tetrahedron 64:3655
Fleckenstein CA, Plenio H (2008) Green Chem 10:563
Gagnon A, Albert V, Duplessis M (2010) Synlett 2936
Kita Y, Morimoto K, Ito M, Ogawa C, Goto A, Dohi T (2009) J Am Chem Soc 131:1668
Dohi T, Ito M, Yamaoka N, Morimoto K, Fujioka H, Kita Y (2010) Angew Chem Int Ed Engl 49:3334
Raduán M, Padrosa J, Pla-Quintana A, Parella T, Roglans A (2011) Adv Synth Catal 353:2003
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Schatz, J., Hoffmann, I. (2014). Thiophene Metallation and Cross-Coupling Chemistry. In: Joule, J. (eds) Thiophenes. Topics in Heterocyclic Chemistry, vol 39. Springer, Cham. https://doi.org/10.1007/7081_2014_127
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