Subscribe to RSS
DOI: 10.1055/s-0040-1706031
Suzuki–Miyaura Coupling Reactions of Fluorohalobenzenes
Dedicated to Professor Ralf Miethchen on the occasion of his 80th birthday
Abstract
Organofluorine compounds have gained interest in the fields of pharmaceuticals, agrochemicals, diagnostics, materials, and catalysis. Suzuki–Miyaura coupling reactions of fluorinated arenes made a tremendous impact in chemical and biological research and made organofluorinated molecules more readily available. This review gives a brief summary of Suzuki–Miyaura coupling reactions of fluorinated benzene derivatives. In this context, various aspects, such as regioselectivity, efficiency, and applications, are discussed.
1 Introduction
2 Organofluorine Compounds
3 Suzuki–Miyaura Reactions of Fluorohalobenzenes
3.1 Fluorophthalates
3.2 Reactions of Pentafluorohalobenzenes
3.3 Tetrafluorohalobenzenes
3.4 Trifluorohalobenzenes
3.5 Difluorohalobenzenes
3.6 Monofluorohalobenzenes
3.7 Halo(trifluoromethyl)benzenes
3.8 Trifluoromethyl Pyridines
4 S Summary
Publication History
Received: 17 February 2021
Accepted after revision: 27 February 2021
Article published online:
01 April 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References and Notes
- 1 Böhm HJ, Banner D, Bendels S, Kansy M, Kuhn B, Müller K, Obst-Sander U, Stahl M. ChemBioChem 2004; 5: 637
- 2 Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
- 3 Kirk KL. Curr. Top. Med. Chem. 2006; 6: 1447
- 4 Watson DA, Su M, Teverovskiy G, Zhang Y, García-Fortanet J, Kinzel T, Buchwald SL. Science 2009; 325: 1661
- 5 Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
- 6 Jeschke P. ChemBioChem 2004; 5: 570
- 7 Theodoridis G. Adv. Fluorine Sci. . Alain T. Elsevier,; 2006. vol. 2, 121-175
- 8 Phelps ME. Proc. Natl. Acad. Sci. U.S.A. 2000; 97: 9226
- 9 Ametamey SM, Honer M, Schubiger PA. Chem. Rev. 2008; 108: 1501
- 10 Pauluth D, Tarumi K. J. Mater. Chem. 2004; 14: 1219
- 11 Suzuki Y, Nonaka O, Koide Y, Okabe N, Hagiwara T, Kawamura I, Yamamoto N, Yamada Y, Kitazume T. Ferroelectrics 1993; 147: 109
- 12 Schreiner PR. Chem. Soc. Rev. 2003; 32: 289
- 13 Wittkopp A, Schreiner PR. Chem. Eur. J. 2003; 9: 407
- 14 Kleiner CM, Schreiner PR. Chem. Commun. 2006; 4315
- 15 Tsogoeva SB. Eur. J. Org. Chem. 2007; 1701
- 16 Kotke M, Schreiner PR. Synthesis 2007; 779
- 17 Schlosser M. Angew. Chem. Int. Ed. 1998; 37: 1496
- 18 Bremer M, Tarumi K. Adv. Mater. 1993; 5: 842
- 19 Li S, Yuan Y, Zhu J, Xie H, Chen Z, Wu Y. Adv. Synth. Catal. 2010; 352: 1582
- 20 de Candia M, Liantonio F, Carotti A, De Cristofaro R, Altomare C. J. Med. Chem. 2009; 52: 1018
- 21 Ishaaya I, Barazani A, Kontsedalov S, Horowitz AR. Entomol. Res. 2007; 37: 148
- 22 Chen H, Viel S, Ziarelli F, Peng L. Chem. Soc. Rev. 2013; 42: 7971
- 23 Robinson JT, Burgess JS, Junkermeier CE, Badescu SC, Reinecke TL, Perkins FK, Zalalutdniov MK, Baldwin JW, Culbertson JC, Sheehan PE. Nano Lett. 2010; 10: 3001
- 24 Guo M, Jian F, He R. J. Fluorine Chem. 2006; 127: 177
- 25 Liedtke J, Loss S, Widauer C, Grützmacher H. Tetrahedron 2000; 56: 143
- 26 Clarke D, Ali MA, Clifford AA, Parratt A, Rose P, Schwinn D, Bannwarth W, Rayner CM. Curr. Top. Med. Chem. 2004; 4: 729
- 27 Lafrance M, Rowley CN, Woo TK, Fagnou K. J. Am. Chem. Soc. 2006; 128: 8754
- 28 Do H.-Q, Daugulis O. J. Am. Chem. Soc. 2008; 130: 1128
- 29 Zhang X, Fan S, He C.-Y, Wan X, Min Q.-Q, Yang J, Jiang Z.-X. J. Am. Chem. Soc. 2010; 132: 4506
- 30 He C.-Y, Fan S, Zhang X. J. Am. Chem. Soc. 2010; 132: 12850
- 31 Wei Y, Su W. J. Am. Chem. Soc. 2010; 132: 16377
- 32 Gouda K.-i, Hagiwara E, Hatanaka Y, Hiyama T. J. Org. Chem. 1996; 61: 7232
- 33 Sahoo AK, Oda T, Nakao Y, Hiyama T. Adv. Synth. Catal. 2004; 346: 1715
- 34 Saeki T, Takashima Y, Tamao K. Synlett 2005; 1771
- 35 Molander GA, Biolatto B. Org. Lett. 2002; 4: 1867
- 36 Kabalka GW, Al-Masum M. Tetrahedron Lett. 2005; 46: 6329
- 37 Adonin NY, Babushkin DE, Parmon VN, Bardin VV, Kostin GA, Mashukov VI, Frohn H.-J. Tetrahedron 2008; 64: 5920
- 38 Burton DJ, Yang Z.-Y. Tetrahedron 1992; 48: 189
- 39 Miyaura N, Yanagi T, Suzuki A. Synth. Commun. 1981; 11: 513
- 40 Suzuki A. Pure Appl. Chem. 1985; 57: 1749
- 41 Wu XF, Anbarasan P, Neumann H, Beller M. Angew. Chem. Int. Ed. 2010; 49: 9047
- 42 Metal-Catalyzed Cross-Coupling Reactions, Vol. 2. De Meijere A, Diederich F. Wiley-VCH; Weinheim: 2004
- 43 Suzuki A. Pure Appl. Chem. 1991; 63: 419
- 44 Suzuki A. Pure Appl. Chem. 1994; 66: 213
- 45 Martin AR, Yang Y. Acta Chem. Scand. 1993; 47: 221
- 46 Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
- 47 Stanforth SP. Tetrahedron 1998; 54: 263
- 48 Akrawi OA, Khan A, Patonay T, Villinger A, Langer P. Tetrahedron 2013; 69: 9013
- 49 Khaddour Z, Eleya N, Akrawi OA, Hamdy AM, Patonay T, Villinger A, Langer P. Tetrahedron Lett. 2013; 54: 5201
- 50 Ibad MF, Zinad DS, Hussain M, Ali A, Villinger A, Langer P. Tetrahedron 2013; 69: 7492
- 51 Akrawi OA, Mohammed HH, Langer P. Synlett 2013; 24: 1121
- 52 Ehlers P, Petrosyan A, Ghochikyan TV, Saghyan AS, Neubauer A, Lochbrunner S, Langer P. Synlett 2013; 24: 359
- 53 Hassan Z, Patonay T, Langer P. Synlett 2013; 24: 412
- 54 Iaroshenko VO, Ali S, Mkrtchyan S, Gevorgyan A, Babar TM, Semeniuchenko V, Hassan Z, Villinger A, Langer P. Tetrahedron Lett. 2012; 53: 7135
- 55 Ali I, Siyo B, Al-Soud Y, Villinger A, Langer P. Synthesis 2012; 44: 1637
- 56a Langer P. Synthesis 2002; 441
- 56b Feist H, Langer P. Synthesis 2007; 327
- 56c Langer P. Eur. J. Org. Chem. 2007; 2233
- 56d Bellur E, Feist H, Langer P. Tetrahedron 2007; 63: 10865
- 56e Feist H, Langer P. Synthesis 2008; 3877
- 56f Hassan Z, Langer P. Synlett 2019; 30: 665
- 56g Nawaz M, Sher M, Langer P. Synlett 2010; 2383
- 56h Langer P. Synlett 2006; 3369
- 56i Langer P. Synlett 2009; 2205
- 57a Smart BE. J. Fluorine Chem. 2001; 109: 3
- 57b Eisenberger P, Gischig S, Togni A. Chem. Eur. J. 2006; 12: 2579
- 58 Schaub T, Radius U. Chem. Eur. J. 2005; 11: 5024
- 59 Park BK, Kitteringham NR, O'Neill PM. Annu. Rev. Pharmacol. Toxicol. 2001; 41: 443
- 60 Ibad MF, Nawaz M, Adeel M, Villinger A, Langer P. Synlett 2010; 195
- 61 Smith RC, Bodner CR, Earl MJ, Sears NC, Hill NE, Bishop LM, Sizemore N, Hehemann DT, Bohn JJ, Protasiewicz JD. J. Organomet. Chem. 2005; 690: 477
- 62 Bandari R, Höche T, Prager A, Dirnberger K, Buchmeiser MR. Chem. Eur. J. 2010; 16: 4650
- 63 Proch S, Mei Y, Villanueva JM. R, Lu Y, Karpov A, Ballauff M, Kempe R. Adv. Synth. Catal. 2008; 350: 493
- 64 Kurscheid B, Belkoura L, Hoge B. Organometallics 2011; 31: 1329
- 65 Irngartinger H, Escher T. Tetrahedron 1999; 55: 10753
- 66 Mu H.-L, Ye W.-P, Song D.-P, Li Y.-S. Organometallics 2010; 29: 6282
- 67 Göttker-Schnetmann I, White P, Brookhart M. J. Am. Chem. Soc. 2004; 126: 1804
- 68 Zhao Q, Li C, Senanayake CH, Tang W. Chem. Eur. J. 2013; 19: 2261
- 69 Mok NY, Chadwick J, Kellett KA. B, Casas-Arce E, Hooper NM, Johnson AP, Fishwick CW. G. J. Med. Chem. 2013; 56: 1843
- 70 Tu T, Sun Z, Fang W, Xu M, Zhou Y. Org. Lett. 2012; 14: 4250
- 71 Thathagar MB, Beckers J, Rothenberg G. J. Am. Chem. Soc. 2002; 124: 11858
- 72 Thathagar MB, Beckers J, Rothenberg G. Adv. Synth. Catal. 2003; 345: 979
- 73 Cano R, Ramón DJ, Yus M. Tetrahedron 2011; 67: 5432
- 74 Nishihara Y, Onodera H, Osakada K. Chem. Commun. 2004; 192
- 75 Yamagata T, Kuwabara J, Kanbara T. Eur. J. Org. Chem. 2012; 5282
- 76 Schaub T, Backes M, Radius U. J. Am. Chem. Soc. 2006; 128: 15964
- 77 Dastgir S, Coleman KS, Cowley AR, Green ML. Organometallics 2010; 29: 4858
- 78 Kuhnert N, Patel C, Jami F. Tetrahedron Lett. 2005; 46: 7575
- 79 Kuster S, Geiger T. Dyes Pigm. 2012; 95: 657
- 80 Mandali PK, Chand DK. Catal. Commun. 2012; 31: 16
- 81 Kniep F, Jungbauer SH, Zhang Q, Walter SM, Schindler S, Schnapperelle I, Herdtweck E, Huber SM. Angew. Chem. Int. Ed. 2013; 52: 7028
- 82 Tzschucke CC, Markert C, Glatz H, Bannwarth W. Angew. Chem. Int. Ed. 2002; 41: 4500
- 83 Morgan BP, Galdamez GA, Gilliard JR. J, Smith RC. Dalton Trans. 2009; 2020
- 84 Sindelar M, Lutz TA, Petrera M, Wanner KT. J. Med. Chem. 2013; 56: 1323
- 85 Liu Y, Feng X, Bao D, Li K, Bao M. J. Mol. Catal. A: Chem. 2010; 323: 16
- 86 Sharif M, Reimann S, Villinger A, Langer P. Synlett 2010; 913
- 87 Sharif M, Maalik A, Reimann S, Feist H, Iqbal J, Patonay T, Villinger A, Langer P. J. Fluorine Chem. 2013; 146: 19
- 88 Dong C.-G, Hu Q.-S. Synlett 2012; 23: 2121
- 89 Sharif M, Zeeshan M, Reimann S, Villinger A, Langer P. Tetrahedron Lett. 2010; 51: 2810
- 90 Ismail MA, Arafa RK, Brun R, Wenzler T, Miao Y, Wilson WD, Generaux C, Bridges A, Hall JE, Boykin DW. J. Med. Chem. 2006; 49: 5324
- 91 Luo Z, Zhu H, Song G, Chang J, Liu R. Dyes Pigm. 2011; 88: 274
- 92 Ali I, Siyo B, Hassan Z, Malik I, Ullah I, Ali A, Nawaz M, Iqbal J, Patonay T, Villinger A. J. Fluorine Chem. 2012; 145: 18
- 93 Ren Y, Bazan GC. Chem. Eur. J. 2010; 16: 11028
- 94 Dubbaka SR, Vogel P. Org. Lett. 2003; 6: 95
- 95 Ahmed S, Sharif M, Shoaib K, Reimann S, Iqbal J, Patonay T, Spannenberg A, Langer P. Tetrahedron Lett. 2013; 54: 1669
For reviews, see: