Synthesis of Propargylic Fluorides toward Carbo- and Heterocycles with Mono- and gem-Difluorinated Side Chains

Abstract

This review reports the synthesis of propargylic derivatives with alkyl chains bearing either one fluorine or a gem-difluoro system. The preparation of the different categories of fluorinated derivatives is analyzed in a systematic manner, based on the nature of substituents close to the fluorine atom(s). In the second part of this review are summarized the synthetic applications of these fluorinated propargylic intermediates, focusing mainly on the preparation of carbo- and heterocyclic derivatives.

1 Introduction

2 Synthesis of Propargylic Fluorides

3 Use of Propargylic Fluorides in the Preparation of Carbo- and Heterocycles with Fluorine-Containing Side Chains

4 Conclusions and Perspectives

Key words

fluorine - alkynes - carbocycles - heterocycles - cycloadditions - cyclocondensations

• References


See, for instance:
• 1a Fluorine Compounds II: A Critical Review, ACS Monograph 187 . American Chemical Society; Washington DC: 1995
• 1b Kitazume T, Yamazaki T. Experimental Methods in Organic Fluorine Chemistry . Gordon and Breach Science Publishers; Tokyo: 1998

For selected reviews on this topic, see:
• 2a Welch JT. Tetrahedron 1987; 43: 3123
• 2b Welch JT. Selective Fluorination in Organic and Bioorganic Chemistry, ACS Symposium Series 456. American Chemical Society; Washington DC: 1991
• 2c Ojima I, McCarthy JR, Welch JT. Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639 . American Chemical Society; Washington DC: 1996
• 2d Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
• 2e Hagmann WK. J. Med. Chem. 2008; 51: 4359
• 2f Fustero S, Sanz-Cervera JF, Acena JL, Sanchez-Rosello M. Synlett 2009; 525
• 2g Hunter L. Beilstein J. Org. Chem. 2010; 6: No. 38
• 2h Qing F-L, Zheng F. Synlett 2011; 1052
• 2i Gillis EP, Eastman KJ, Hill MD, Donnelly DJ, Meanwell NA. J. Med. Chem. 2015; 58: 8315
• 2j Zhou Y, Wang J, Gu Z, Wang S, Zhu W, Acena JL, Soloshonok VA, Izawa K, Liu H. Chem. Rev. 2016; 116: 422
• 2k Yerien DE, Bonesi S, Postigo A. Org. Biomol. Chem. 2016; 14: 8398; and references cited therein

For reviews on propargylic fluorides, see:
• 3a Prakesch M, Grée D, Grée R. Acc. Chem. Res. 2002; 35: 175
• 3b Prakesch M, Grée D, Chandrasekhar S, Grée R. Eur. J. Org. Chem. 2005; 1221
• 3c Pacheco MC, Purser S, Gouverneur V. Chem. Rev. 2008; 108: 1943
• 3d Arimitsu S, Hammond GB. Chim. Oggi 2010; 28: 20
• 3e Jin Z, Hammond GB, Xu B. Aldrichimica Acta 2012; 45: 67; and references cited therein
• 4 Middleton WJ. J. Org. Chem. 1975; 40: 574
• 5 Poulter CD, Wiggins PL, Plummer TL. J. Org. Chem. 1981; 46: 1532
• 6a Kalman TI, Nie Z. Nucleosides Nucleotides Nucleic Acids 2000; 19: 357
• 6b Kalman TI, Nie Z, Kamat A. Bioorg. Med. Chem. Lett. 2000; 10: 391
• 7 Nair V, Bera B, Kern ER. Nucleosides Nucleotides Nucleic Acids 2003; 22: 115
• 8 Khanous A, Gorgues A, Cousseau J. J. Fluorine Chem. 1990; 49: 401
• 9 Pomper MG, Kochanny MJ, Thieme AM, Carlson KE, Vanbrocklin HF, Mathias CJ, Welch MJ, Katzenellenbogen JA. Nucl. Med. Biol. 1992; 19: 461
• 10 Dasilva JN, Crouzel C, Stulzaft O, Khalili-Varasteh M, Hantraye P. Nucl. Med. Biol. 1992; 19: 167
• 11 Wüst F, Carlson KE, Katzenellenbogen JA. Steroids 2003; 68: 177
• 12a Munyemana F, Frisque-Hesbain A.-M, Devos A, Ghosez L. Tetrahedron Lett. 1989; 30: 3077
• 12b Tietze LF, Bothe U, Schuberth I. Chem. Eur. J. 2000; 6: 836
• 13a Sanders TC, Hammond GB. J. Org. Chem. 1993; 58: 5598
• 13b Wang Z, Gu Y, Zapata AJ, Hammond GB. J. Fluorine Chem. 2001; 107: 127
• 13c Benayoud F, deMendonca DJ, Digits CA, Moniz GA, Sanders TC, Hammond GB. J. Org. Chem. 1996; 61: 5159
• 13d Zapata AJ, Gu Y, Hammond GB. J. Org. Chem. 2000; 65: 227
• 14 Castelhano AL, Krantz A. J. Am. Chem. Soc. 1987; 109: 3491
• 15 Lan Y, Hammond GB. J. Org. Chem. 2000; 65: 4217
• 16 Xu Z.-Q, Qiu Y.-L, Chokekijchai S, Mitsuya H, Zemlicka J. J. Med. Chem. 1995; 38: 875
• 17a Riyadh SM, Ishii H, Fuchigami T. Tetrahedron Lett. 2001; 42: 3009
• 17b Riyadh SM, Ishii H, Fuchigami T. Tetrahedron 2001; 57: 8817
• 17c Riyadh SM, Ishii H, Fuchigami T. Tetrahedron 2002; 58: 5877
• 17d Riyadh SM, Fuchigami T. J. Org. Chem. 2002; 67: 9379
• 18 Rye CS, Baell JB, Street I. Tetrahedron 2007; 63: 3306
• 19a Grée D, Madiot V, Grée R. Tetrahedron Lett. 1999; 40: 6403
• 19b Filmon J, Grée R, Grée R. J. Fluorine Chem. 2001; 107: 271
• 20 Das S, Chandrasekhar S, Yadav JS, Grée R. Tetrahedron Lett. 2007; 48: 5305
• 21 Madiot V, Lesot P, Grée D, Courtieu J, Grée R. Chem. Commun. 2000; 169
• 22 Prakesch M, Grée D, Grée R. J. Org. Chem. 2001; 66: 3146
• 23 Manthati VL, Sai Krishna Murthy A, Caijo F, Drouin D, Lesot P, Grée D, Grée R. Tetrahedron: Asymmmetry 2006; 17: 2306
• 24 Grée D, Grée R. Tetrahedron Lett. 2007; 48: 5435
• 25 Blayo A-L, Le Meur S, Grée D, Grée R. Adv. Synth. Catal. 2008; 350: 471
• 26 Bannwarth P, Valleix A, Grée D, Grée R. J. Org. Chem. 2009; 74: 4646
• 27 Prakesch M, Kerouredan E, Grée D, Grée R, DeChancie J, Houk KN. J. Fluorine Chem. 2004; 125: 537
• 28 De Jonghe S, Van Overmeire I, Van Calenbergh S, Hendrix C, Busson R, De Keukeleire D, Herdewinj P. Eur. J. Org. Chem. 2000; 3177
• 29 Grée D, Madiot V, Grée R. Tetrahedron Lett. 1999; 40: 6399
• 30 Cheng L.-J, Cordier CJ. Angew. Chem. Int. Ed. 2015; 54: 13734
• 31 Kornilov AM, Sorochinskii AE, Kukhar VP. Zh. Org. Khim. 1989; 25: 2520; J. Org. Chem. USSR (Engl. Transl.) 1989, 25, 2260
• 32a Asai T, Morizawa Y, Shimada T, Nakayama T, Urushihara M, Matsamura Y, Yasuda A. Tetrahedron Lett. 1995; 36: 273
• 32b Matsamura Y, Shimada T, Nakayama T, Urushihara M, Asai T, Morizawa Y, Yasuda A. Tetrahedron 1995; 51: 8771
• 32c Matsamura Y, Asai T, Shimada T, Nakayama T, Urushihara M, Morizawa Y, Yasuda A, Yamamoto T, Fujitani B, Hosoki K. Chem. Pharm. Bull. 1995; 43: 353
• 32d Matsamura Y, Shimada T, Wang S-Z, Asai T, Morizawa Y, Yasuda A. Bull. Chem. Soc. Jpn. 1996; 69: 3523
• 33 Shimidzu M, Kanemoto S, Nakhara Y. Heterocycles 2000; 52: 117
• 34 Carroll L, Pacheco MC, Garcia L, Gouverneur V. Chem. Commun. 2006; 4113
• 35 Lan Y, Hammond GB. Org. Lett. 2002; 4: 2437
• 36 Xu B, Hammond GB. J. Org. Chem. 2006; 71: 3518
• 37 Dear RE. A, Gilbert EE. J. Org. Chem. 1968; 33: 819
• 38 Kumar V, Rodger C, Bell MR. J. Org. Chem. 1995; 60: 4591
• 39 Van Niel MB, Collins I, Beer MS, Broughton HB, Cheng SK. F, Goodacre SC, Head A, Locker KL, MacLeod AM, Morrison D, Moyes CR, O’Connor D, Pike A, Rowley M, Russell MG. N, Sohal B, Stanton JA, Thomas S, Verrier H, Watt AP, Castro JL. J. Med. Chem. 1999; 42: 2087
• 40a Shavrin KN, Gvozdev VD, Nefedov OM. Russ. Chem. Bull. 1997; 46: 1973
• 40b Shavrin KN, Gvozdev VD, Nefedov OM. Izv. Akad. Nauk., Ser. Khim. 2002; 1143; Russ. Chem. Bull. (Engl. Transl.) 2002, 46, 1237
• 41 Konno T, Kitazume T. Chem. Commun. 1996; 2227
• 42 Aikawa K, Maruyama K, Nitta J, Hashimoto R, Mikami K. Org. Lett. 2016; 18: 3354
• 43 Zhang W, Wang F, Hu J. Org. Lett. 2009; 11: 2109
• 44 Zhu S-Q, Xu X-H, Qing F.-L. Org. Chem. Front. 2015; 2: 1022
• 45 Burton DJ, Hartgraves GA. J. Fluorine Chem. 2007; 128: 1198
• 46 Rico I, Cantacuzene D, Wakselman C. J. Chem. Soc., Perkin Trans. 2 1982; 1063
• 47 Wang Z, Hammond GB. Chem. Commun. 1999; 2545
• 48 Xu B, Mae M, Hong JA, Li Y, Hammond GB. Synthesis 2006; 803
• 49 Hammond GB. J. Fluorine Chem. 2006; 127: 476
• 50a Romanenko VD, Kukhar VP. Chem. Rev. 2006; 106: 3868
• 50b Benayoud F, Hammond GB. Chem. Commun. 1996; 1447
• 51a Zhang X, Burton DJ. Tetrahedron Lett. 2000; 41: 7791
• 51b Zhang X, Burton DJ. J. Fluorine Chem. 2002; 116: 15
• 52 Jiang J, Chu L, Qing F.-L. Org. Lett. 2012; 14: 2870
• 53 Hanzawa Y, Inazawa K, Kon A, Aoki H, Kobayashi Y. Tetrahedron Lett. 1987; 28: 659
• 54 Wang Z, Hammond GB. Tetrahedron Lett. 2000; 41: 2339
• 55a Arimitsu S, Hammond GB. J. Org. Chem. 2006; 71: 8665
• 55b You Z.-W, Jiang Z.-X, Wang B.-L, Qing F.-L. J. Org. Chem 2006; 71: 7261
• 55c Xu J, Zhang X, Qiu X-L, Qing F-L. Synthesis 2009; 602
• 56 Arimitsu S, Jacobsen JM, Hammond GB. Tetrahedron Lett. 2007; 48: 1625
• 57a Fustero S, Fernandez B, Bello P, del Pozo C, Arimitsu S, Hammond GB. Org. Lett. 2007; 9: 4251
• 57b Arimitsu S, Fernandez B, del Pozo C, Fustero S, Hammond GB. J. Org. Chem. 2008; 73: 2656
• 58 Zemtsov AA, Volodin AD, Levin VV, Struchkova MI, Dilman AD. Beilstein J. Org. Chem. 2015; 11: 2145
• 59 Kerouredan E, Prakesch M, Grée D, Grée R. Lett. Org. Chem. 2004; 1: 78
• 60 Manthati VL, Grée D, Grée R. Eur. J. Org. Chem. 2005; 3825
• 61 Bannwarth P, Grée D, Grée R. Tetrahedron Lett. 2010; 51: 2413
• 62 Khalaf A, Grée D, Abdallah H, Jaber N, Hachem A, Grée R. Tetrahedron 2011; 67: 3881
• 63 Yu Y.-B, He G.-Z, Zhang X. Angew. Chem. Int. Ed. 2014; 53: 10457
• 64 Zhang B, Zhang X. Chem. Commun. 2016; 52: 1238
• 65 Chen F, Hashmi AS. K. Org. Lett. 2016; 18: 2880
• 66 Li X, Li S, Sun S, Yang F, Zhu W, Zhu Y, Wu Y, Wu Y. Adv. Synth. Catal. 2016; 358: 1699
• 67a Graham SM, Prestwich GD. J. Org. Chem. 1994; 59: 2956
• 67b Hudlicky M. J. Fluorine Chem. 1989; 44: 345
• 68 Prakesch M, Grée D, Grée R. Tetrahedron 2003; 59: 8833
• 69 Lin J, Qiu X.-L, Qing F.-L. Beilstein J. Org. Chem. 2010; 6: No. 37
• 70 Liang S, Hammond GB, Xu B. Chem. Commun. 2016; 52: 6013
• 71 Grée D, Grée R. Tetrahedron Lett. 2010; 51: 2218
• 72 Nasr El Dine A, Grée D, Roisnel T, Caytan E, Hachem A, Grée R. Eur. J. Org. Chem. 2016; 556
• 73 Pujari SA, Kaliappan KP, Valleix A, Grée D, Grée R. Synlett 2008; 2503
• 74a Fustero S, Bello P, Miro J, Sanchez-Rosello M, Haufe G, del Pozzo C. Beilstein J. Org. Chem. 2013; 9: 2688
• 74b Fustero S, Bello P, Miro J, Simon A, del Pozzo C. Chem. Eur. J. 2012; 18: 10991
• 75 Arimitsu S, Hammond GB. Beilstein J. Org. Chem. 2010; 6: No. 48
• 76 Bannwarth P, Grée D, Aubert C, Grée R. J. Fluorine Chem. 2014; 162: 32

For recent discussions on the design and use of chemical libraries in medicinal chemistry and drug discovery, see:
• 77a Lauck F, Rarey M. J. Chem. Inf. Model. 2016; 56: 1641
• 77b Taylor RD, MacCoss M, Lawson AD. G. J. Med. Chem. 2017; in press; DOI: 10.1021/acs.jmedchem.6b01367 and references cited therein
• 78 Bannwarth P, Grée D, Das S, Yadav JS, Grée R. J. Fluorine Chem. 2012; 134: 180
• 79 Arimitsu S, Hammond GB. J. Org. Chem. 2007; 72: 8559
• 80 Arimitsu S, Bottom RL, Hammond GB. J. Fluorine Chem. 2008; 129: 1047
• 81 Hariss L, Bouhadir KH, Roisnel T, Grée R, Hachem A. Synlett 2017; 28: 195
• 82 Yamazaki T, Kawasaki-Takasuka T, Furuta A, Sakamoto S. Tetrahedron 2009; 65: 5945
• 83 Nasr El Dine A, Khalaf A, Grée D, Tasseau O, Fares F, Jaber N, Lesot P, Hachem A, Grée R. Beilstein J. Org. Chem. 2013; 9: 1943
• 84 Nasr El Dine A, Tasseau O, Grée D, Roisnel T, Khalaf A, El-Abdallah S, Fares F, Hachem A, Grée R. Synlett 2014; 25: 2451