Transition-Metal-Catalyzed Alkylation of Polyfluoroarenes through C–F Bond Cleavage

Qian Zhang; Tao Xiong; Qian Zhang

doi:10.1055/a-1479-8264

Synlett, Table of Contents

Synlett 2021; 32(14): 1379-1384
DOI: 10.1055/a-1479-8264

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Transition-Metal-Catalyzed Alkylation of Polyfluoroarenes through C–F Bond Cleavage

Qian Zhang

^aJilin Province Key Laboratory of Organic Functional Molecular Design and Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, P. R. of China

,

Tao Xiong ∗

^aJilin Province Key Laboratory of Organic Functional Molecular Design and Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, P. R. of China

,

Qian Zhang∗

^aJilin Province Key Laboratory of Organic Functional Molecular Design and Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, P. R. of China

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China

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Abstract

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Abstract

The polyfluoroarenes are a subgroup of organofluorines that are widely utilized in both medicinal chemistry and materials science. We briefly summarize recent advances in the synthesis of these important compounds, with particular attention to our recent CuH-catalyzed defluorinative alkylation of polyfluoroarenes with alkenes in a highly site-selective C–F bond-cleavage fashion.

1 Introduction

2 Transition-Metal-Catalyzed Alkylation through Selective C–F Bond Cleavage

3 CuH-Catalyzed Defluorinative Alkylation of Polyfluoroarenes with Alkenes

4 Summary and Outlook

Key words

polyfluoroarenes - C–F bond cleavage - copper catalysis - alkylation - alkenes

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References

References

1a Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
1b O’Hagan D. Chem. Soc. Rev. 2008; 37: 308
1c Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
1d Jeschke P. ChemBioChem 2004; 5: 570
1e Ametamey SM, Honer M, Schubiger PA. Chem. Rev. 2008; 108: 1501
1f Cametti M, Crousse B, Metrangolo P, Milani R, Resnati G. Chem. Soc. Rev. 2012; 41: 31
1g Berger R, Resnati G, Metrangolo P, Weber E, Hulliger J. Chem. Soc. Rev. 2011; 40: 3496

2a Brown JM, Gouverneur V. Angew. Chem. Int. Ed. 2009; 48: 8610
2b Furuya T, Kamlet AS, Ritter T. Nature 2011; 473: 470
2c Liang T, Neumann CN, Ritter T. Angew. Chem. Int. Ed. 2013; 52: 8214
2d Campbell MG, Ritter T. Chem. Rev. 2015; 115: 612
2e Preshlock S, Tredwell M, Gouverneur V. Chem. Rev. 2016; 116: 719

3a Weck M, Dunn AR, Matsumoto K, Coates GW, Lobkovsky EB, Grubbs RH. Angew. Chem. Int. Ed. 1999; 38: 2741
3b Sakamoto Y, Suzuki T, Miura A, Fujikawa H, Tokito S, Taga Y. J. Am. Chem. Soc. 2000; 122: 1832
3c Nitschke JR, Tilley TD. J. Am. Chem. Soc. 2001; 123: 10183
3d Tsuzuki T, Shirasawa N, Suzuki T, Tokito S. Adv. Mater (Weinheim, Ger.) 2003; 15: 1455
3e Meyer EA, Castellano RK, Diederich F. Angew. Chem. Int. Ed. 2003; 42: 1210
3f Babudri F, Farinola GM, Naso F, Ragni R. Chem. Commun. 2007; 1003

4a Lafrance M, Rowley CN, Woo TK, Fagnou K. J. Am. Chem. Soc. 2006; 128: 8754
4b Do H.-Q, Daugulis O. J. Am. Chem. Soc. 2008; 130: 1128
4c Simonetti M, Perry GJ. P, Cambeiro XC, Juliá-Hernández F, Arokianathar JN, Larrosa I. J. Am. Chem. Soc. 2016; 138: 3596
4d Li W, Yuan D, Wang G, Zhao Y, Xie J, Li S, Zhu C. J. Am. Chem. Soc. 2019; 141: 3187

5a Zhang X, Fan S, He C.-Y, Wan X, Min Q.-Q, Yang J, Jiang Z.-X. J. Am. Chem. Soc. 2010; 132: 4506
5b Nett AJ, Zhao W, Zimmerman PM, Montgomery J. J. Am. Chem. Soc. 2015; 137: 7636

6 Wei Y, Zhao H, Kan J, Su W, Hong M. J. Am. Chem. Soc. 2010; 132: 2522

7a Fan S, Chen F, Zhang X. Angew. Chem. Int. Ed. 2011; 50: 5918
7b Yao T, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed. 2011; 50: 2990
7c Xie W, Chang S. Angew. Chem. Int. Ed. 2016; 55: 1876

8a Fan S, He C.-Y, Zhang X. Chem. Commun. 2010; 46: 4926
8b Sun Z.-M, Zhang J, Manan RS, Zhao P. J. Am. Chem. Soc. 2010; 132: 6935
8c Xu S, Wu G, Ye F, Wang X, Li H, Zhao X, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2015; 54: 4669
8d Xie W, Heo J, Kim D, Chang S. J. Am. Chem. Soc. 2020; 142: 7487

9 Xie W, Yoon JH, Chang S. J. Am. Chem. Soc. 2016; 138: 12605

10a Meier G, Braun T. Angew. Chem. Int. Ed. 2009; 48: 1546
10b Clot E, Eisenstein O, Jasim N, Macgregor SA, McGrady JE, Perutz RN. Acc. Chem. Res. 2011; 44: 333
10c Kuehnel MF, Lentz D, Braun T. Angew. Chem. Int. Ed. 2013; 52: 3328
10d Aizenberg M, Milstein D. Science 1994; 265: 359
10e Aizenberg M, Milstein D. J. Am. Chem. Soc. 1995; 117: 8674
10f Schaub T, Fischer P, Steffen A, Braun T, Radius U, Mix A. J. Am. Chem. Soc. 2008; 130: 9304
10g Lv H, Zhan J.-H, Cai Y.-B, Yu Y, Wang B, Zhang J.-L. J. Am. Chem. Soc. 2012; 134: 16216
10h Fischer P, Götz K, Eichhorn A, Radius U. Organometallics 2012; 31: 1374
10i Zhan J.-H, Lv HB, Yu Y, Zhang J.-L. Adv. Synth. Catal. 2012; 354: 1529
10j Lv HB, Cai Y.-B, Zhang J.-L. Angew. Chem. Int. Ed. 2013; 52: 3203
10k Senaweera SM, Singh A, Weaver JD. J. Am. Chem. Soc. 2014; 136: 3002
10l Lu J, Khetrapal NS, Johnson JA, Zeng XC, Zhang J. J. Am. Chem. Soc. 2016; 138: 15805
10m Cybulski MK, Nicholls JE, Lowe JP, Mahon MF, Whittlesey MK. Organometallics 2017; 36: 2308

11a Braun T, Ahijado Salomon M, Altenhöer K, Teltewskoi M, Hinze S. Angew. Chem. Int. Ed. 2009; 48: 1818
11b Teltewskoi M, Panetier JA, Macgregor SA, Braun T. Angew. Chem. Int. Ed. 2010; 49: 3947
11c Lindup RJ, Marder TB, Perutz RN, Whitwood AC. Chem. Commun. 2007; 3664
11d Liu XW, Echavarren J, Zarate C, Martin R. J. Am. Chem. Soc. 2015; 137: 12470
11e Niwa T, Ochiai H, Watanabe Y, Hosoya T. J. Am. Chem. Soc. 2015; 137: 14313
11f Kalläne SI, Teltwskoi M, Braun T, Braun B. Organometallics 2015; 34: 1156
11g Zhou J, Kuntze-Fechner MW, Bertermann R, Paul US. D, Berthel JH. J, Friedrich A, Du Z, Marder TB, Radius U. J. Am. Chem. Soc. 2016; 138: 5250
11h Tian Y.-M, Guo X.-N, Kuntze-Fechner MW, Krummenacher I, Braunschweig H, Radius U, Steffen A, Marder TB. J. Am. Chem. Soc. 2018; 140: 17612

For Ni-catalyzed arylations, see:

12a Yoshikai N, Mashima H, Nakamura E. J. Am. Chem. Soc. 2005; 127: 17978
12b Schaub T, Backes M, Radius U. J. Am. Chem. Soc. 2006; 128: 15964
12c Sun AD, Love JA. Org. Lett. 2011; 13: 2750
12d Tobisu M, Xu T, Shimasaki T, Chatani N. J. Am. Chem. Soc. 2011; 133: 19505
12e Nakamura Y, Yoshikai N, Ilies L, Nakamura E. Org. Lett. 2012; 14: 3316
12f Ohashi M, Saijo H, Shibata M, Ogoshi S. Eur. J. Org. Chem. 2013; 443
12g Saijo H, Sakaguchi H, Ohashi M, Ogoshi S. Organometallics 2014; 33: 3669
12h Zhou J, Berthel JH. J, Kuntze-Fechner MW, Friedrich A, Marder TB, Radius U. J. Org. Chem. 2016; 81: 5789
12i Zhu F, Wang Z.-X. J. Org. Chem. 2014; 79: 4285

For Pd-catalyzed arylations, see:

12j Macgregor SA, Roe DC, Marshall WJ, Bloch KM, Bakhmutov VI, Grushin VV. J. Am. Chem. Soc. 2005; 127: 15304
12k Cargill MR, Sandford G, Tadeusiak AJ, Yufit DS, Howard JA. K, Kilickiran P, Nelles G. J. Org. Chem. 2010; 75: 5860
12l Yu D, Lu L, Shen Q. Org. Lett. 2013; 15: 940
12m Ohashi M, Doi R, Ogoshi S. Chem. Eur. J. 2014; 20: 2040
12n Luo Z.-J, Zhao H.-Y, Zhang X. Org. Lett. 2018; 20: 2543

13a Wang T, Alfonso BJ, Love JA. Org. Lett. 2007; 9: 5629
13b Buckley HL, Sun AD, Love JA. Organometallics 2009; 28: 6622
13c Sun AD, Love JA. J. Fluorine Chem. 2010; 131: 1237
13d Sun AD, Leung K, Restivo AD, LaBerge NA, Takasaki H, Love JA. Chem. Eur. J. 2014; 20: 3162
13e Yang X, Sun H, Zhang S, Li X. J. Organomet. Chem. 2013; 723: 36
13f Xiao S.-H, Xiong Y, Zhang X.-X, Cao S. Tetrahedron 2014; 70: 4405

14 Guo H, Kong F, Kanno K.-i, He J, Nakajima K, Takahashi T. Organometallics 2006; 25: 2045

15a Iwasaki T, Fukuoka A, Min X, Yokoyama W, Kuniyasu H, Kambe N. Org. Lett. 2016; 18: 4868
15b Iwasaki T, Okamoto K, Kuniyasu H, Kambe N. Chem. Lett. 2017; 46: 1504
15c Iwasaki T, Min X, Fukuoka A, Zhu L, Qiu R, Yang T, Ehara M, Sudalai A, Kambe N. J. Org. Chem. 2018; 83: 9267

16a Rendler S, Oestreich M. Angew. Chem. Int. Ed. 2007; 46: 498
16b Deutsch C, Krause N, Lipshutz BH. Chem. Rev. 2008; 108: 2916
16c Fujihara T, Semba K, Terao J, Tsuji Y. Catal. Sci. Technol. 2014; 4: 1699
16d Pirnot MT, Wang Y.-M, Buchwald SL. Angew. Chem. Int. Ed. 2016; 55: 48
16e Jordan AJ, Lalic G, Sadighi JP. Chem. Rev. 2016; 116: 8318
16f Chen J, Guo Z, Lu Z. Chin. J. Chem. 2018; 36: 1075
16g Liu RY, Buchwald SL. Acc. Chem. Res. 2020; 53: 1229

17a Semba K, Ariyama K, Zheng H, Kameyama R, Sakaki S, Nakao Y. Angew. Chem. Int. Ed. 2016; 55: 6275
17b Friis SD, Pirnot MT, Buchwald SL. J. Am. Chem. Soc. 2016; 138: 8372
17c Friis SD, Pirnot MT, Dupuis LN, Buchwald SL. Angew. Chem. Int. Ed. 2017; 56: 7242
17d Armstrong MK, Goodstein MB, Lalic G. J. Am. Chem. Soc. 2018; 140: 10233
17e Armstrong MK, Lalic G. J. Am. Chem. Soc. 2019; 141: 6173
17f Kortman GD, Hull KL. ACS Catal. 2017; 7: 6220

18a Xu G, Zhao H, Fu B, Cang A, Zhang G, Zhang Q, Xiong T, Zhang Q. Angew. Chem. Int. Ed. 2017; 56: 13130
18b Xu G, Fu B, Zhao H, Li Y, Zhang G, Wang Y, Xiong T, Zhang Q. Chem. Sci. 2019; 10: 1802
18c Fu B, Yuan X, Li Y, Wang Y, Zhang Q, Xiong T, Zhang Q. Org. Lett. 2019; 21: 3576
18d Wang H, Zhang G, Zhang Q, Wang Y, Li Y, Xiong T, Zhang Q. Chem. Commun. 2020; 56: 1819
18e Zhang G, Liang Y, Qin T, Xiong T, Liu S, Guan W, Zhang Q. CCS Chem. 2020; 2: 1737

19 Li X, Fu B, Zhang Q, Yuan X, Zhang Q, Xiong T, Zhang Q. Angew. Chem. Int. Ed. 2020; 59: 23056