Improvements in Efficiency and Selectivity for C–F Bond Halogen-Exchange Reactions by Using Boron Reagents

Andrej Ćorković; Andreas Dorian; Florence J. Williams

doi:10.1055/a-1941-2205

Synlett, Inhaltsverzeichnis

Synlett 2023; 34(03): 193-202
DOI: 10.1055/a-1941-2205

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Improvements in Efficiency and Selectivity for C–F Bond Halogen-Exchange Reactions by Using Boron Reagents

Andrej Ćorković‡

^aUniversity of Iowa, Chemistry Building, Iowa City, IA 52246, USA

,

Andreas Dorian‡

^bUniversity of Alberta, 11227 Saskatchewan Drive, Edmonton, AB T6G-2G2, Canada

,

Florence J. Williams ∗

^aUniversity of Iowa, Chemistry Building, Iowa City, IA 52246, USA

› Institutsangaben

Abstract

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Abstract

The use of boron Lewis acids as instigators of bond cleavage offers a number of synthetic possibilities. A unique feature of this class of reagents is the ability to functionalize otherwise inert C–F bonds. We summarize notable developments in C–F bond halogen exchange using Lewis acidic boron reagents and we conclude by featuring our group’s advances in activating CF₃ groups by using boron trihalides.

1 Introduction

2 Boron-Mediated Halogen Exchange

3 Mono-Selective C–F Activation

4 Conclusions

Key words

halogen exchange - boron trihalides - C–F bond activation - trifluoromethyl group activation - C–F functionalization - Lewis acids

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Referenzen

References

For boron tribromide as a reagent, see:

1a Suzuki A, Hara S, Huang X. Boron Tribromide. In Encyclopedia of Reagents for Organic Synthesis. Wiley; New York: 2006.
1b Punna S, Meunier S, Finn MG. Org. Lett. 2004; 6: 2777

2a Hall DG. Chem. Soc. Rev. 2019; 48: 3475
2b Ishihara K, Yamamoto H. Eur. J. Org. Chem. 1999; 1999: 527
2c Dimitrijević E, Taylor MS. ACS Catal. 2013; 3: 945
2d Rao B, Kinjo R. Chem. Asian J. 2018; 13: 1279

For alternative types of boron-catalyzed processes, see:

3a Bage AD, Nicholson K, Hunt TA, Langer T, Thomas SP. ACS Catal. 2020; 10: 13479
3b Kumar G, Roy S, Chatterjee I. Org. Biomol. Chem. 2021; 19: 1230

4 Babcock L, Pizer R. Inorg. Chem. 1980; 19: 56
5 Atienza BJ. P, Truong N, Williams FJ. Org. Lett. 2018; 20: 6332
6 Dorian A, Landgreen EJ, Petras HR, Shepherd JJ, Williams FJ. Chem. Eur. J. 2021; 27: 10839
7 Zain M, Kazmi H, Karmakar A, Michaelis VK, Williams FJ. Tetrahedron 2019; 75: 1465
8 Gupta R, Young RD. Synthesis 2022; 54: 1671

For a general overview of C–F activation strategies, see:

9a Ahrens T, Kohlmann J, Ahrens M, Braun T. Chem. Rev. 2015; 115: 931
9b Burdeniuc J, Jedlicka B, Crabtree RH. Chem. Ber. 1996; 130: 145
9c Amii H, Uneyama K. Chem. Rev. 2009; 109: 2119
9d O’Hagan D. Chem. Soc. Rev. 2008; 37: 308

10 Jaroschik F. Chem. Eur. J. 2018; 24: 14572
11 Grant DJ, Dixon DA. J. Phys. Chem. A 2009; 113: 777
12 Blanksby SJ, Ellison GB. Acc. Chem. Res. 2003; 36: 255
13 Lemal DM. J. Org. Chem. 2004; 69: 1
14 Glockler G. J. Phys. Chem. 1959; 63: 828
15 Inoue M, Sumii Y, Shibata N. ACS Omega 2020; 5: 10633
16 Ogawa Y, Tokunaga E, Kobayashi O, Hirai K, Shibata N. iScience 2020; 23: 101467
17 Berger R, Resnati G, Metrangolo P, Weber E, Hulliger J. Chem. Soc. Rev. 2011; 40: 3496
18 Alonso C, Martinez de Marigorta E, Rubiales G, Palacios F. Chem. Rev. 2015; 115: 1847
19 Guidotti J, Schanen V, Tordeux M, Wakselman C. J. Fluorine Chem. 2005; 126: 443
20 Heijnen D, Gualtierotti J.-B, Hornillos V, Feringa BL. Chem. Eur. J. 2016; 22: 3991
21 Bhasin KK, Gupta V, Sharma RP. Synth. Commun. 1993; 23: 1863
22 Rajca A, Rajca S, Wongsriratanakul J, Ross CR. Polyhedron 2001; 20: 1669

23a Barbero M, Cadamuro S, Degani I, Fochi R, Gatti A, Regondi V. Synthesis 1986; 1074
23b Belen’kii LI, Brokhovetskii DB, Krayushkin MM. Tetrahedron 1990; 46: 1659
23c Chatterjee T, Kim DI, Cho EJ. J. Org. Chem. 2018; 83: 7423

24 Chivers T. Can. J. Chem. 1970; 48: 3856
25 Yoshida S, Shimomori K, Kim Y, Hosoya T. Angew. Chem. Int. Ed. 2016; 55: 10406
26 Richmond TG, Shriver DF. Organometallics 1983; 2: 1061
27 Richmond TG, Shriver DF. Organometallics 1984; 3: 305
28 Tyrra W, Naumann D. J. Fluorine Chem. 1989; 45: 401
29 Namavari M, Satyamurthy N, Phelps ME, Barrio JR. Tetrahedron Lett. 1990; 31: 4973
30 Namavari M, Satyamurthy N, Barrio JR. J. Fluorine Chem. 1995; 72: 89
31 Swarnakar AK, Hering-Junghans C, Ferguson MJ, McDonald R, Rivard E. Chem. Eur. J. 2017; 23: 8628

32a Gu W, Haneline MR, Douvris C, Ozerov OV. J. Am. Chem. Soc. 2009; 131: 11203
32b Stahl T, Klare HF. T, Oestreich M. ACS Catal. 2013; 3: 1578

33 Jaiswal AK, Prasad PK, Young RD. Chem. Eur. J. 2019; 25: 6290
34 Prakash GK. S, Hu J, Simon J, Bellew DR, Olah GA. J. Fluorine Chem. 2004; 125: 595
35 Luo Y.-R. Comprehensive Handbook of Chemical Bond Energies. CRC Press; Boca Raton: 2007

36a Zhu J, Ni C, Gao B, Hu J. J. Fluorine Chem. 2015; 171: 139
36b Liebing P, Oehler F, Wagner M, Tripet PF, Togni A. Organometallics 2018; 37: 570
36c Uno M, Sumino S, Fukuyama T, Matsuura M, Kuroki Y, Kishikawa Y, Ryu I. J. Org. Chem. 2019; 84: 9330
36d Zhang K.-F, Bian K.-J, Li C, Sheng J, Li Y, Wang X.-S. Angew. Chem. Int. Ed. 2019; 58: 5069
36e Tang X.-J, Zhang Z, Dolbier WR. Jr. Chem. Eur. J. 2015; 21: 18961
36f Zhang Z, Tang X, Dolbier WR. Jr. Org. Lett. 2015; 17: 4401
36g Li C, Cao Y.-X, Wang R, Wang Y.-N, Lan Q, Wang X.-S. Nat. Commun. 2018; 9: 4951
36h Ren L, Wang Q. ChemistrySelect 2018; 3: 709
36i Yu X, Cai L, Bao M, Sun Q, Ma H, Yuan C, Xu W. Chem. Commun. 2020; 56: 1685
36j Ma Y, Roy S, Kong X, Chen Y, Liu D, Hider RC. J. Med. Chem. 2012; 55: 2185
36k Chen H, Yin J, Lin Y. Chem. Zvesti 2009; 63: 92

37 Sumino S, Uno M, Fukuyama T, Ryu I, Matsuura M, Yamamoto A, Kishikawa Y. J. Org. Chem. 2017; 82: 5469
38 Ikeda M, Matsuzawa T, Morita T, Hosoya T, Yoshida S. Chem. Eur. J. 2020; 26: 12333
39 Sun Q, Yu X, Bao M, Liu M, Pan J, Zha Z, Cai L, Ma H, Yuan C, Qiu X, Xu W. Angew. Chem. Int. Ed. 2018; 57: 4035

40a Meanwell NA. J. Med. Chem. 2011; 54: 2529
40b Boyer J, Arnoult E, Médebielle M, Guillemont J, Unge J, Jochmans D. J. Med. Chem. 2011; 54: 7974

41a Yoshida M, Morinaga M, Iyoda M. J. Fluorine Chem. 1994; 68: 33
41b Guidotti J, Metz F, Tordeux M, Wakselman C. Synlett 2004; 1759
41c Gu J.-W, Guo W.-H, Zhang X. Org. Chem. Front. 2015; 2: 38
41d Verhoog S, Pfeifer L, Khotavivattana T, Calderwood S, Collier T, Wheelhouse K, Tredwell M, Gouverneur V. Synlett 2015; 27: 25

42a Wang H, Jui NT. J. Am. Chem. Soc. 2018; 140: 163
42b Chen K, Berg N, Gschwind R, König B. J. Am. Chem. Soc. 2017; 139: 18444
42c Luo Y.-C, Tong F.-F, Zhang Y, He C.-Y, Zhang X. J. Am. Chem. Soc. 2021; 143: 13971

43 Vogt DB, Seath CP, Wang H, Jui NT. J. Am. Chem. Soc. 2019; 141: 13203
44 Stephan DW. Acc. Chem. Res. 2015; 48: 306
45 Caputo CB, Stephan DW. Organometallics 2012; 31: 27
46 Mandal D, Gupta R, Young RD. J. Am. Chem. Soc. 2018; 140: 10682

47a Mandal D, Gupta R, Jaiswal AK, Young RD. J. Am. Chem. Soc. 2020; 142: 2572
47b Gupta R, Mandal D, Jaiswal AK, Young RD. Org. Lett. 2021; 23: 1915

48 Weissman SA, Anderson NG. Org. Process Res. Dev. 2015; 19: 1605

49a Janjetovic M, Ekebergh A, Träff AM, Hilmersson G. Org. Lett. 2016; 18: 2804
49b Goh KK. K, Sinha A, Fraser C, Young RD. RSC Adv. 2016; 6: 42708

50a Treder AP, Andruszkiewicz R, Zgoda W, Walkowiak A, Ford C, Hudson AL. Bioorg. Med. Chem. 2011; 19: 156
50b Wang R, Gregg BT, Zhang W, Golden KC, Quinn JF, Cui P, Tymoshenko DO. Tetrahedron Lett. 2009; 50: 7070

51 Liu H, Kondo S.-i, Takeda N, Unno M. Eur. J. Inorg. Chem. 2009; 1317