Application of Industrially Relevant HydroFluoroOlefin (HFO) Gases in Organic Syntheses

Bálint Varga; János T. Csenki; Balázs L. Tóth; Ferenc Béke; Zoltán Novák; András Kotschy

doi:10.1055/a-1538-8344

Synthesis, Table of Contents

Synthesis 2021; 53(23): 4313-4326
DOI: 10.1055/a-1538-8344

short review

Application of Industrially Relevant HydroFluoroOlefin (HFO) Gases in Organic Syntheses

Bálint Varga

^aELTE ‘Lendület’ Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Faculty of Science, Eötvös Loránd University, Pázmány Péter stny. 1/A, 1117 Budapest, Hungary

,

János T. Csenki

^aELTE ‘Lendület’ Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Faculty of Science, Eötvös Loránd University, Pázmány Péter stny. 1/A, 1117 Budapest, Hungary

,

Balázs L. Tóth

^aELTE ‘Lendület’ Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Faculty of Science, Eötvös Loránd University, Pázmány Péter stny. 1/A, 1117 Budapest, Hungary

,

Ferenc Béke

^aELTE ‘Lendület’ Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Faculty of Science, Eötvös Loránd University, Pázmány Péter stny. 1/A, 1117 Budapest, Hungary

,

Zoltán Novák ∗

^aELTE ‘Lendület’ Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Faculty of Science, Eötvös Loránd University, Pázmány Péter stny. 1/A, 1117 Budapest, Hungary

,

András Kotschy ∗

^bServier Research Institute of Medicinal Chemistry, Záhony utca 7, 1031 Budapest, Hungary

› Author Affiliations

Abstract

All articles of this category

Abstract

Hydrofluoroolefin (HFO) gases are state-of-the-art cooling agents with widespread household and industrial applications. Considering their structural benefits these fluorous feedstocks have gained the attention of organic chemists in the last couple of years. In this short review we summarized the existing synthetic transformations of these gaseous starting material and present their applicability in the synthesis of fluorine-containing organic molecules, which have potential importance as building blocks and reagents for diverse syntheses.

1 Introduction

2 Addition Reactions

3 Substitutions

4 Organometallic Chemistry

4.1 Organolithium Compounds

4.2 Organometallic Complexes

4.3 Silicon Organic Chemistry

4.4 Boron Organic Chemistry

4.5 Palladium-Catalyzed Transformations

4.6 Metathesis

4.7 Hydroesterification, Hydroformylation

5 Conclusions

Key words

HFO - hydrofluoroolefin - fluorine - fluoroalkylation - transition metals

Full Text

References

References
1 Balázs L. Tóth current address: Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain.

2a Fried J, Sabo EF. J. Am. Chem. Soc. 1953; 75: 2273
2b Fried J, Sabo EF. J. Am. Chem. Soc. 1954; 76: 1455
2c Robinson RC. V. JAMA, J. Am. Med. Assoc. 1955; 157: 1300

3a Johnson BM, Shu Y.-Z, Zhuo X, Meanwell NA. J. Med. Chem. 2020; 63: 6315
3b Inoue M, Sumii Y, Shibata N. ACS Omega 2020; 5: 10633
3c Fujiwara T, O’Hagan D. J. Fluorine Chem. 2014; 167: 16
3d Han J, Remete AM, Dobson LS, Kiss L, Izawa K, Moriwaki H, Soloshonok VA, O’Hagan D. J. Fluorine Chem. 2020; 239: 109639
3e Mei H, Remete AM, Zou Y, Moriwaki H, Fustero S, Kiss L, Soloshonok VA, Han J. Chin. Chem. Lett. 2020; 31: 2401
3f Wang J, Sánches-Rosello M, Aceny JL, del Pozo C, Sorochinsky AE, Fustero S, Soloshonok VA, Liu J. Chem. Rev. 2014; 114: 2432
3g Zhou Y, Wang J, Gu Z, Wang S, Zhu W, Acena JL, Soloshonok VA, Izawa K, Liu H. Chem. Rev. 2016; 116: 422
3h Maienfisch P, Hall RG. Chimia 2004; 58: 93
3i Gillis EP, Eastman KJ, Hill MD, Donnely DJ, Meanwell NA. J. Med. Chem. 2015; 58: 8315
3j Meanwell NA. J. Med. Chem. 2018; 61: 5822
3k Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
3l Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
3m Jeschke P. ChemBioChem 2004; 5: 570

4 Han J, Kiss L, Mei H, Remete AM, Ponikvar-Svet M, Sedgwick DM, Roman R, Fustero S, Moriwaki H, Soloshonok VA. Chem. Rev. 2021; 121: 4678

5a Yerein DE, Bonesi S, Postigo A. Org. Biomol. Chem. 2016; 14: 8398
5b Lectard S, Hamashima Y, Sodeoka M. Adv. Synth. Catal. 2010; 352: 2708
5c O’Hagan D, Deng H. Chem. Rev. 2015; 115: 634
5d Pihko PM. Angew. Chem. Int. Ed. 2006; 45: 544
5e Kohlhepp SV, Gulder T. Chem. Soc. Rev. 2016; 45: 6270
5f Szpera R, Moseley DF. J, Smith LB, Sterling AJ, Gouverneur V. Angew. Chem. Int. Ed. 2019; 58: 14824
5g Lin A, Huehls CB, Yang J. Org. Chem. Front. 2014; 1: 434
5h Testa C, Roger J, Fleurat-Lessard P, Hierso J.-C. Eur. J. Org. Chem. 2019; 233

6a Li X, Shi X, Li X, Shi D. Beilstein J. Org. Chem. 2019; 15: 2213
6b Furuya T, Kamlet AS, Ritter T. Nature 2011; 473: 470
6c Yang X, Wu T, Phipps RJ, Toste FD. Chem. Rev. 2015; 115: 826
6d Ni C, Hu M, Hu J. Chem. Rev. 2015; 115: 765
6e Bizet V, Besset T, Ma J.-A, Cahard D. Curr. Top. Med. Chem. 2014; 14: 901
6f Han Z.-Z, Zhang C.-P. Adv. Synth. Catal. 2020; 10: 11980
6g Kawamura S, Sodeoka M. Bull. Chem. Soc. Jpn. 2019; 92: 1245
6h Zhao Y, Liu F. Tetrahedron Lett. 2018; 59: 180
6i Barata-Vallejo S, Bonesi SM, Postigo A. Org. Biomol. Chem. 2015; 13: 11153
6j Lantaño B, Torviso MR, Bonesi SM, Barata-Vallejo S, Postigo A. Coord. Chem. Rev. 2015; 285: 76
6k Bhaskaran RP, Babu BP. Adv. Synth. Catal. 2020; 362: 5219
6l Tomashenko OA, Grushin VV. Chem. Rev. 2011; 111: 4475
6m Charpentier J, Früh N, Togni A. Chem. Rev. 2015; 115: 650
6n Studer A. Angew. Chem. Int. Ed. 2012; 51: 8950
6o Xu X.-H, Matsuzaki K, Shibata N. Chem. Rev. 2015; 115: 731
6p Alonso C, Martínez de Marigorta E, Rubiales G, Palacios F. Chem. Rev. 2015; 115: 1847
6q Ma J.-A, Cahard D. J. Fluorine Chem. 2007; 128: 975
6r Pan X, Xia H, Wu J. Org. Chem. Front. 2016; 3: 1163

7 Caron S. Org. Process Res. Dev. 2020; 24: 470

8a Sicard AJ, Baker RT. Chem. Rev. 2020; 120: 9164
8b Bellabarba RM. J. Fluorine Chem. 2021; 244: 109741

9 Feiring AE. J. Org. Chem. 1980; 45: 1962
10 Taguchi T, Tomizawa G, Nakajima M, Kobayashi Y. Chem. Pharm. Bull. 1985; 33: 4077
11 Delacroix K, Perez M, Petit L. J. Fluorine Chem. 2020; 235: 109538
12 Zhao B, Lu J.-Y, Li Y, Tu D.-H, Liu Z.-T, Liu Z.-W, Lu J. RSC Adv. 2015; 5: 101412
13 Varga B, Tóth BL, Béke F, Csenki JT, Kotschy A, Novák Z. Org. Lett. 2021; 23: 4925
14 Gaede B, Balthazor TM. J. Org. Chem. 1983; 48: 276
15 Ojima I, Yatabe M, Fuchikami T. J. Org. Chem. 1982; 47: 2051
16 Tanaka K, Mori T, Mitsuhashi K. Bull. Chem. Soc. Jpn. 1993; 66: 263
17 Skalenko YA, Druzhenko TV, Denisenko AV, Samoilenko MV, Dacenko OP, Trofymchuk SA, Grygorenko OO, Tolmachev AA, Mykhailiuk PK. J. Org. Chem. 2018; 83: 6275
18 Murray BJ, Marsh TG. F, Yufit DS, Fox MA, Harsányi A, Boulton LT, Sandford G. Eur. J. Org. Chem. 2020; 6236

19a Kobayashi Y, Kumadaki I, Takahashi M, Yamauchi T. J. Fluorine Chem. 1982; 21: 73
19b Takusari H, Okazaki S. Chem. Lett. 1984; 13: 885

20a Kobayashi Y, Nagai T, Kumadaki I, Takahashi M, Yamauchi T. Chem. Pharm. Bull. 1984; 32: 4382
20b Gyenes F, Purrington ST, Liu Y.-S. J. Org. Chem. 1999; 64: 1366
20c Calvo B, Wuttke J, Braun T, Kemnitz E. ChemCatChem 2016; 8: 1945

21 Meißner G, Kretschmar K, Braun T, Kemnitz E. Angew. Chem. Int. Ed. 2017; 56: 16338
22 Lanzinger D, Höhlein IM, Weiß SB, Rieger B. J. Organomet. Chem. 2015; 778: 21
23 Jaeger AD, Ehm C, Lentz D. Chem. Eur. J. 2018; 24: 6769
24 Phillips NA, White AJ. P, Crimmin MR. Adv. Synth. Catal. 2019; 361: 3351

25a Kraft BM, Jones WD. J. Am. Chem. Soc. 2002; 124: 8681
25b Vela J, Smith JM, Yu Y, Ketterer NA, Flaschenriem CJ, Lachicotte RJ, Holland PL. J. Am. Chem. Soc. 2005; 127: 7857
25c Rieth RD, Brennessel WW, Jones WD. Eur. J. Inorg. Chem. 2007; 2839
25d Ahrens T, Teltewskoi M, Ahrens M, Braun T, Laubenstein R. Dalton Trans. 2016; 45: 17495

26 Moritz FK, Lenz D. Angew. Chem. Int. Ed. 2010; 49: 2933
27 Kuehnel MF, Holstein P, Kliche M, Krüger J, Matthies S, Nitsch D, Schutt J, Sparenberg M, Lentz D. Chem. Eur. J. 2012; 18: 10701
28 Clot E, Megret C, Kraft BM, Eisenstein O, Jones WD. J. Am. Chem. Soc. 2004; 126: 5647
29 Andrella NO, Xu N, Gabidullin BM, Ehm C, Baker RT. J. Am. Chem. Soc. 2019; 141: 11506
30 Krüger J, Leppkes J, Ehm C, Lentz D. Chem. Asian J. 2016; 11: 3062
31 Hiraoka Y, Kawasaki-Takasuka T, Morizawa Y, Yamazaki T. J. Fluorine Chem. 2015; 179: 71
32 Yagupolskii YL, Pavlenko NV, Shelyazhenko SV, Filatov AA, Kremlev MM, Mushta AI, Gerus II, Peng S, Petrov VA, Nappa M. J. Fluorine Chem. 2015; 179: 134
33 Murray BJ, Ball ED, Harsányi A, Sandford G. Eur. J. Org. Chem. 2019; 7666
34 Kendrick DA, Kolb M. J. Fluorine Chem. 1989; 45: 265
35 Ye F, Ge Y, Spannenberg A, Neumann H, Xu L.-W, Beller M. Nat. Commun. 2021; 12: 3257

36a Fujita T, Ichitsuka T, Fuchibe K, Ichikawa J. Chem. Lett. 2011; 40: 986
36b Ichitsuka T, Takanohashi T, Fujita T, Ichikawa J. J. Fluorine Chem. 2015; 170: 29

37 Brisdon AK, Pritchard RG, Thomas A. Organometallics 2012; 31: 1341
38 Tolman CA. J. Am. Chem. Soc. 1974; 96: 2780
39 Dorta R, Stevens ED, Scott NM, Costabile C, Cavallo L, Hoff CD, Nolan SP. J. Am. Chem. Soc. 2005; 127: 2485
40 Alluhaibi LM, Brisdon AK, Pritchard RG. J. Fluorine Chem. 2017; 203: 146
41 Vela J, Vaddadi S, Cundari TR, Smith JM, Gregory EA, Lachicotte RJ, Flaschenriem CJ, Holland PL. Organometallics 2004; 23: 5226
42 Bakewell C, White AJ. P, Crimmin MR. Angew. Chem. Int. Ed. 2018; 57: 6638

43a Talavera M, von Hahmann CN, Müller R, Ahrens M, Kaupp M, Braun T. Angew. Chem. Int. Ed. 2019; 58: 10688
43b Talavera M, Braun T. Synlett 2020; 31: 1760

44 Slaney ME, Anderson DJ, Ferguson MJ, McDonald R, Cowie M. Organometallics 2012; 31: 2286
45 Black RE, Kilyanek SM, Reinhart ED, Jordan RF. Organometallics 2019; 38: 4250
46 Wada S, Jordan RF. Angew. Chem. Int. Ed. 2017; 56: 1820
47 Braun T, Noveski D, Neumann B, Stammler H.-G. Angew. Chem. Int. Ed. 2002; 41: 2745
48 Noveski D, Braun T, Schulte M, Neumann B, Stammler H.-G. Dalton Trans. 2003; 4075
49 Ohashi M, Shibata M, Ogoshi S. Angew. Chem. Int. Ed. 2014; 53: 13578
50 Slaney ME, Anderson DJ, Ferguson MJ, McDonald R, Cowie M. J. Am. Chem. Soc. 2010; 132: 16544
51 Braun T, Wehmeier F, Altenhöner K. Angew. Chem. Int. Ed. 2007; 46: 5321
52 Braun T, Salomon MA, Altenhöner K, Teltewskoi M, Hinze S. Angew. Chem. Int. Ed. 2009; 48: 1818
53 Trnka TM, Day MW, Grubbs RH. Angew. Chem. Int. Ed. 2001; 40: 3441
54 VenkatRamani S, Schrock RR, Hoveyda AH, Müller P, Tsay C. Organometallics 2018; 37: 1641
55 Hiyama T, Obayashi M, Sawahata M. Tetrahedron Lett. 1983; 24: 4113
56 Fujita M, Obayashi M, Hiyama T. Tetrahedron 1988; 44: 4135
57 Sakaguchi H, Ohashi M, Ogoshi S. Angew. Chem. Int. Ed. 2018; 57: 328
58 Coates G, Tan HY, Klaff C, White AJ. P, Crimmin MR. Angew. Chem. Int. Ed. 2019; 58: 12514
59 Larichev RB, Petrov VA, Grier GJ, Nappa MJ, Marshall WJ, Marchione AA, Dooley RJ. Org. Process Res. Dev. 2014; 18: 1060
60 Pavlenko NV, Peng S, Petrov V, Jackson A, Sun X, Sprague L, Yagupolskii YL. Eur. J. Org. Chem. 2020; 5425
61 Phillips JR, Stone FG. A. J. Chem. Soc. 1962; 94
62 Brown HC, Chen G.-M, Jennings MP, Ramachandran PV. Angew. Chem. Int. Ed. 1999; 38: 2052
63 Sakaguchi H, Uetake Y, Ohashi M, Niwa T, Ogoshi S, Hosoya T. J. Am. Chem. Soc. 2017; 139: 12855
64 Phillips NA, Coates GJ, White AJ. P, Crimmin MR. Chem. Eur. J. 2020; 26: 5365
65 Ramachandran PV, Jennings MP, Brown HC. Org. Lett. 1999; 1: 1399
66 Fuchikami T, Yatabe M, Ojima I. Synthesis 1981; 365
67 Casanti A, Gemoets HP. L, Motti E, Della Ca’ N, Noël T. Chem. Eur. J. 2018; 24: 14079
68 Kang J.-P, Lu J.-Y, Li Y, Wang Z.-X, Mao W, Lu J. RSC Adv. 2016; 6: 39387
69 Li Y, Tu D.-H, Gu Y.-J, Wang B, Wang Y.-Y, Liu Z.-T, Liu Z.-W, Lu J. Eur. J. Org. Chem. 2015; 4340
70 Heitz W, Knebelkamp A. Makromol. Chem., Rapid Commun. 1991; 12: 69
71 Ohashi M, Saijo H, Shibata M, Ogoshi S. Eur. J. Org. Chem. 2013; 443
72 Fustero S, Simón-Fuentes A, Barrio P, Haufe G. Chem. Rev. 2015; 115: 871
73 Imhof S, Randl S, Blechert S. Chem. Commun. 2001; 1692
74 Macnaughtan ML, Gary JB, Gerlach DL, Johnson MJ. A, Kampf JW. Organometallics 2009; 28: 2880
75 Takahira Y, Morizawa Y. J. Am. Chem. Soc. 2015; 137: 7031
76 Koh MJ, Nguyen TT, Lam JK, Torker S, Hyvl J, Schrock RR, Hoveyda AH. Nature 2017; 542: 80
77 Mu Y, Nguyen TT, van der Mei FW, Schrock RR, Hoveyda AH. Angew. Chem. Int. Ed. 2019; 58: 5365
78 Fuchikami T, Ohishi K, Ojima I. J. Org. Chem. 1983; 48: 3803
79 Ojima I, Kato K, Okabe M, Fuchikami T. J. Am. Chem. Soc. 1987; 109: 7714
80 Ohtsuka Y, Kobayashi O, Yamakawa T. J. Fluorine Chem. 2014; 161: 34
81 Shibahara F, Nozaki K, Hiyama T. J. Am. Chem. Soc. 2003; 125: 8555