Suzuki–Miyaura Coupling Reactions of Fluorohalobenzenes

Shoaib Iqbal; Muhammad Sharif; Peter Langer

doi:10.1055/s-0040-1706031

Synlett, Table of Contents

Synlett 2021; 32(18): 1784-1795
DOI: 10.1055/s-0040-1706031

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Suzuki–Miyaura Coupling Reactions of Fluorohalobenzenes

Shoaib Iqbal

^aInstitut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany URL: http://www.langer.chemie.uni-rostock.de/

^bLeibniz-Institut für Katalyse an der Universität Rostock e. V., Albert-Einstein-Str. 29a, 18059 Rostock, Germany

^cDepartment of Chemistry, COMSATS Institute of Information Technology, 22060, Abbottabad, Pakistan

,

Muhammad Sharif

^aInstitut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany URL: http://www.langer.chemie.uni-rostock.de/

^bLeibniz-Institut für Katalyse an der Universität Rostock e. V., Albert-Einstein-Str. 29a, 18059 Rostock, Germany

,

Peter Langer ∗

^aInstitut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany URL: http://www.langer.chemie.uni-rostock.de/

^bLeibniz-Institut für Katalyse an der Universität Rostock e. V., Albert-Einstein-Str. 29a, 18059 Rostock, Germany

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Abstract

All articles of this category

Dedicated to Professor Ralf Miethchen on the occasion of his 80^th 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

Keywords

arenes - catalysis - fluorine - Suzuki–Miyaura reaction

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References

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

For reviews, see:

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