Catalysis for fluorination and trifluoromethylation

Nature

Volumn 473, Issue 7348, 2011, Pages 470-477

  Furuya, Takeru ^a,b   Kamlet, Adam S ^a   Ritter, Tobias ^a  

^a HARVARD UNIVERSITY   (United States)

^b Life Sciences Research   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARGON; CALIFORNIUM; CARBON; FLUORINE; METAL; ORGANOFLUORINE DERIVATIVE; PALLADIUM;

CATALYSIS; DRUG; FLUORINE; METABOLISM;

CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; ELECTROPHILICITY; ENANTIOSELECTIVITY; FLUORINATION; METHYLATION; NUCLEOPHILICITY; PRIORITY JOURNAL; REVIEW; THERMOSTABILITY; TRIFLUOROMETHYLATION;

ARGON; CARBON; CATALYSIS; FLUORINE; HALOGENATION; METHYLATION;

EID: 79957603696     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/nature10108     Document Type: Review

References (100)

1. Mü ller, K., Faeh, C. & Diederich, F. Fluorine in pharmaceuticals: looking beyond intuition. Science 317, 1881-1886 (2007).
2. Purser, S., Moore, P. R., Swallow, S. & Gouverneur, V. Fluorine in medicinal chemistry. Chem. Soc. Rev. 37, 320-330 (2008).
3. Jeschke, P. The unique role of fluorine in the design of active ingredients for modern crop production. ChemBioChem 5, 570-589 (2004). (Pubitemid 39257080)
4. Hung, M. H., Farnham, W. B., Feiring, A. E. & Rozen, S. in Fluoropolymers: Synthesis Vol. 1 (eds Hougham, G., Cassidy, P. E., Johns, K. & Davidson, T.) 51-66 (Plenum, 1999).
5. Ametamey, S. M., Honer, M. & Schubiger, P. A. Molecular imaging with PET. Chem. Rev. 108, 1501-1516 (2008). (Pubitemid 351796395)
6. O'Hagan, D. Understanding organofluorine chemistry. An introduction to the C2F bond. Chem. Soc. Rev. 37, 308-319 (2008).
7. Curran, D. P. Strategy-level separations in organic synthesis: from planning to practice. Angew. Chem. Int. Edn 37, 1174-1196 (1998). (Pubitemid 28253421)
8. Patterson, J. C. II& Mosley, M. L. How available is positron emission tomography in the United States? Mol. Imaging Biol. 7, 197-200 (2005). (Pubitemid 41348860)
9. Kirk, K. L. Fluorination in medicinal chemistry: methods, strategies, and recent developments. Org. Process Res. Dev. 12, 305-321 (2008).
10. Furuya, T., Kuttruff, C. A. & Ritter, T. Carbon-fluorine bond formation. Curr. Opin. Drug Discov. Dev. 11, 803-819 (2008).
11. Grushin, V. V. The organometallic fluorine chemistry of palladium and rhodium: studies toward aromatic fluorination. Acc. Chem. Res. 43, 160-171 (2010).
12. Furuya, T., Klein, J. E. M. N. & Ritter, T. C-F bond formation for the synthesis of aryl fluorides. Synthesis 1804-1821 (2010).
13. Kirsch, P.Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications (Wiley, 2004).
14. Gribble, G. W. in Progress in the Chemistry of Organic Natural Products Vol. 68 (eds Herz, W., Kirby, G. W., Moore, R. E., Steglich, W. & Tamm, C.) 1-498 (Springer, 1996).
15. Gribble, G. W. in Progress in the Chemistry of Organic Natural Products Vol. 91 (eds Kinghord, A. D., Falk, H. & Kobayashi, J.) 1-613 (Springer, 2009).
16. O'Hagan, D., Schaffrath, C., Cobb, S. L., Hamilton, J. T. G. & Murphy, C. D. Biochemistry: Biosynthesis of an organofluorine molecule. Nature 416, 279 (2002).
17. Dong, C. et al. Crystal structure and mechanismof a bacterial fluorinating enzyme. Nature 427, 561-565 (2004). (Pubitemid 38209116)
18. Shannon, R. D. Revised effective ionic radii and systematic studies of interatomic distances in halides and chalcogenides. Acta Crystallogr. A 32, 751-767 (1976).
19. Emsley, J. Very strong hydrogen bonds. Chem. Soc. Rev. 9, 91-124 (1980).
20. Adams, D. J. & Clark, J. H. Nucleophilic routes to selectively fluorinated aromatics. Chem. Soc. Rev. 28, 225-231 (1999).
21. Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds (CRC Press, 2002).
22. Subramanian, M. A.& Manzer, L. E.A "greener" synthetic route for fluoroaromatics via copper(II) fluoride. Science 297, 1665 (2002). (Pubitemid 35000773)
23. Cope, A. C. & Siekman, R. W. Formation of covalent bonds from platinum or palladium to carbon by direct substitution. J. Am. Chem. Soc. 87, 3272-3273 (1965).
24. Hull, K. L., Anani, W. Q.& Sanford, M. S. Palladium-catalyzed fluorinationof carbon- hydrogen bonds. J. Am. Chem. Soc. 128, 7134-7135 (2006). Describes the first Pd-catalysed C2F bond formation. (Pubitemid 43849095)
25. Wang, X.,Mei, T.-S.& Yu, J.-Q. VersatilePd(OTf)2?2H2O-catalyzedortho- fluorination using NMP as a promoter. J. Am. Chem. Soc. 131, 7520-7521 (2009).
26. Yamada, S., Gavryushin, A. & Knochel, P. Convenient electrophilic fluorination of functionalized aryl and heteroarylmagnesiumreagents. Angew. Chem. Int. Edn 49, 2215-2218 (2010).
27. Anbarasan, P., Neumann, H.& Beller, M. Efficient synthesis of aryl fluorides. Angew. Chem. Int. Edn 49, 2219-2222 (2010).
28. Powers, D. C. & Ritter, T. Bimetallic Pd(III) complexes in palladium-catalysed carbon2heteroatom bond formation. Nature Chem. 1, 302-309 (2009).
29. Kaspi, A. W., Yahav-Levi, A., Goldberg, I. & Vigalok, A. Xenon difluoride induced aryl iodide reductive elimination: a simple access to difluoropalladium(II) complexes. Inorg. Chem. 47, 5-7 (2008).
30. Ball, N. D. & Sanford, M. S. Synthesis and reactivity of a mono-s-aryl palladium(IV) fluoride complex. J. Am. Chem. Soc. 131, 3796-3797 (2009).
31. Furuya, T. & Ritter, T. Carbon2fluorine reductive elimination from a high-valent palladium fluoride. J. Am. Chem. Soc. 130, 10060-10061 (2008).
32. Furuya, T. et al. Mechanism of C2F reductive elimination from palladium(IV) fluorides. J. Am. Chem. Soc. 132, 3793-3807 (2010).
33. Fraser, S. L., Antipin Yu, M., Khroustalyov, V. N. & Grushin, V. V. Molecular fluoro palladium complexes. J. Am. Chem. Soc. 119, 4769-4770 (1997). (Pubitemid 27261725)
34. Pilon, M. C. & Grushin, V. V. Synthesis and characterization of organopalladium complexes containing a fluoro ligand. Organometallics 17, 1774-1781 (1998). (Pubitemid 128595603)
35. Grushin, V. V. Palladium fluoride complexes: one more step toward metalmediated C2F bond formation. Chem. Eur. J. 8, 1006-1014 (2002).
36. Yandulov, D. V. & Tran, N. T. Aryl-fluoride reductive elimination from Pd(II): feasibility assessment from theory and experiment. J. Am. Chem. Soc. 129, 1342-1358 (2007). (Pubitemid 46208607)
37. Grushin, V. V. & Marshall, W. J. Ar-F reductive elimination from palladium(II) revisited. Organometallics 26, 4997-5002 (2007). (Pubitemid 47524323)
38. Watson, D. A. et al. Formation of ArF from LPdAr(F): catalytic conversion of aryl triflates to aryl fluorides. Science 325, 1661-1664 (2009).
39. Fors, B. P., Watson, D. A., Biscoe, M. R. & Buchwald, S. L. A highly active catalyst for Pd-catalyzed amination reactions: cross-coupling reactions using aryl mesylates and the highly selective monoarylation of primary amines using aryl chlorides. J. Am. Chem. Soc. 130, 13552-13554 (2008).
40. Furuya, T., Kaiser, H. M. & Ritter, T. Palladium-mediated fluorination of arylboronic acids. Angew. Chem. Int. Edn 47, 5993-5996 (2008).
41. Furuya, T.& Ritter, T. Fluorination of boronic acidsmediated by silver(I) triflate. Org. Lett. 11, 2860-2863 (2009).
42. Furuya, T., Strom, A. E. & Ritter, T. Silver-mediated fluorination of functionalized aryl stannanes. J. Am. Chem. Soc. 131, 1662-1663 (2009).
43. Tang, P., Furuya, T.& Ritter, T. Silver-catalyzed late-stage fluorination. J.Am. Chem. Soc. 132, 12150-12154 (2010).
44. Azizian, H., Eaborn, C. & Pidcock, A. Synthesis of organotrialkylstannanes. The reaction between organic halides and hexaalkyldistannanes in the presence of palladium complexes. J. Organomet. Chem. 215, 49-58 (1981).
45. Powers, D. C., Benitez, D., Tkatchouk, E., Goddard, W. A. III & Ritter, T. Bimetallic reductive elimination from dinuclear Pd(III) complexes. J. Am. Chem. Soc. 132, 14092-14103 (2010).
46. Ma, J.-A. & Cahard, D. Strategies for nucleophilic, electrophilic, and radical trifluoromethylations. J. Fluor. Chem. 128, 975-996 (2007).
47. Shimizu, M. & Hiyama, T. Modern synthetic methods for fluorine-substituted target molecules. Angew. Chem. Int. Edn 44, 214-231 (2005). (Pubitemid 40094974)
48. Bott, G., Field, L. D. & Sternhell, S. Steric effects. A study of a rationally designed system. J. Am. Chem. Soc. 102, 5618-5626 (1980).
49. Jensen, M. B. et al. Reactivity and structure of CF3I on Ru(001). J. Phys. Chem. 99, 8736-8744 (1995).
50. Liu, Z.-M., Zhou, X.-L., Kiss, J.& White, J. M. Interaction of CF3I withPt(111). Surf. Sci. 286, 233-245 (1993).
51. Yagupolskii, L. M. in Houben-Weyl: Methods of Organic Chemistry Vol. E10a, Organo- Fluorine Compounds (eds Baasner, B., Hagemann, H. & Tatlow, J.-C.) 509-534 (Thieme, 2000).
52. Clark, H. C. & Tsai, J. H. Bonding in fluorinated organometallic compounds. J. Organomet. Chem. 7, 515-517 (1967).
53. Grushin, V. V. & Marshall, W. J. Facile Ar2CF3 bond formation at Pd. Strikingly different outcomes of reductive elimination from [(Ph3P)2Pd(CF3)Ph] and [(Xantphos)Pd(CF3)Ph]. J. Am. Chem. Soc. 128, 12644-12645 (2006). (Pubitemid 44527732)
54. Culkin, D. A. & Hartwig, J. F. Carbon-carbon bond-forming reductive elimination fromarylpalladiumcomplexes containing functionalized alkyl groups. Influence of ligand steric and electronic properties on structure, stability, and reactivity. Organometallics 23, 3398-3416 (2004).
55. Grushin, V. V. & Marshall, W. J. Unexpected H2O-induced Ar2X activation with trifluoromethylpalladium(II) aryls. J. Am. Chem. Soc. 128, 4632-4641 (2006).
56. Ball, N. D., Kampf, J. W. & Sanford, M. S. Aryl-CF3 bond-forming reductive elimination from palladium(IV). J. Am. Chem. Soc. 132, 2878-2879 (2010).
57. Ye, Y., Ball, N. D., Kampf, J. W. & Sanford, M. S. Oxidation of a cyclometalated Pd(II) dimer with "CF3 1": formation and reactivity of a catalytically competent monomeric Pd(IV) aquo complex. J. Am. Chem. Soc. 132, 14682-14687 (2010).
58. Mcloughlin, V. C. R. & Thrower, J. A route to fluoroalkyl-substituted aromatic compounds involving fluoroalkylcopper intermediates. Tetrahedron 25, 5921-5940 (1969).
59. Kobayashi, Y. & Kumadaki, I. Trifluoromethylation of aromatic compounds. Tetrahedr. Lett. 10, 4095-4096 (1969).
60. Carr, G. E., Chambers, R. D., Holmes, T. F. & Parker, D. G. Sodium perfluoroalkane carboxylates as sources of perfluoroalkyl groups. J. Chem. Soc. Perkin Trans. I 921-926 (1988).
61. Oishi, M., Kondo, H. & Amii, H. Aromatic trifluoromethylation catalytic in copper. Chem. Commun. 1909-1911 (2009).
62. Wiemers, D. A. & Burton, D. J. Pregeneration, spectroscopic detection, and chemical reactivity of (trifluoromethyl)copper, an elusive and complex species. J. Am. Chem. Soc. 108, 832-834 (1986).
63. Dubinina, G. G., Furutachi, H. & Vicic, D. A. Active trifluoromethylating agents from well-defined copper(I)-CF3 complexes. J.Am. Chem. Soc. 130, 8600-8601 (2008). (Pubitemid 351962487)
64. Dubinina, G. G., Ogikubo, J. & Vicic, D. A. Structure of bis(trifluoromethyl)cuprate and its role in trifluoromethylation reactions. Organometallics 27, 6233-6235 (2008).
65. Monnier, F. & Taillefer, M. Catalytic C2C, C2N, and C2O Ullmann-type coupling reactions. Angew. Chem. Int. Edn 48, 6954-6971 (2009).
66. Altman, R. A.,Hyde, A. M.,Huang, X.& Buchwald, S. L. OrthogonalPd- andCu-based catalyst systems for C- and N-arylation of oxindoles. J. Am. Chem. Soc. 130, 9613-9620 (2008). (Pubitemid 352031175)
67. Tye, J. W.,Weng, Z., Johns, A. M., Incarvito, C. D.& Hartwig, J. F. Copper complexes of anionic nitrogen ligands in the amidation and imidation of aryl halides. J. Am. Chem. Soc. 130, 9971-9983 (2008).
68. Huffman, L. M. & Stahl, S. S. Carbon2nitrogen bond formation involving welldefined aryl2copper(III) complexes. J. Am. Chem. Soc. 130, 9196-9197 (2008). (Pubitemid 352031107)
69. Knauber, T., Arikan, F., Röschenthaler, G.-V. & Gooßen, L. J. Copper-catalyzed trifluoromethylation of aryl iodides with potassium (trifluoromethyl) trimethoxyborate. Chem. Eur. J. 17, 2689-2697 (2011).
70. Chu, L. & Qing, F.-L. Copper-mediated oxidative trifluoromethylation of boronic acids. Org. Lett. 12, 5060-5063 (2010).
71. Zhang, C.-P. et al. Copper-mediated trifluoromethylation of heteroaromatic compounds by trifluoromethyl sulfonium salts. Angew. Chem. Int. Edn 50, 1896-1900 (2011).
72. Senecal, T. D., Parsons, A. T. & Buchwald, S. L. Room temperature aryl trifluoromethylation via copper-mediated oxidative cross-coupling. J. Org. Chem. 76, 1174-1176 (2011).
73. Morimoto, H., Tsubogo, T., Litvinas, N. D. & Hartwig, J. F. A broadly applicable copper reagent for trifluoromethylations and perfluoroalkylations of aryl iodides and bromides. Angew. Chem. Int. Edn50, 3793-3798 (2011); published online 25 March 2011.
74. Cho, E. J. et al. The palladium-catalyzed trifluoromethylation of aryl chlorides. Science 328, 1679-1681 (2010).
75. Wang, X., Truesdale, L. & Yu, J.-Q. Pd(II)-catalyzed ortho-trifluoromethylation of arenes using TFA as a promoter. J. Am. Chem. Soc. 132, 3648-3649 (2010).
76. Ma, J.-A. & Cahard, D. Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions. Chem. Rev. 108, PR1-PR43 (2008).
77. Lectard, S., Hamashima, Y. & Sodeoka, M. Recent advances in catalytic enantioselective fluorination reactions. Adv. Synth. Catal. 352, 2708-2732 (2010).
78. Shibata, N., Mizuta, S. & Kawai, H. Recent advances in enantioselective trifluoromethylation reactions. Tetrahedr. Asymm. 19, 2633-2644 (2008).
79. Young, S.Note on the formation of an alcoholic fluoride. J. Chem. Soc.39, 489-497 (1881).
80. Umemoto, T. & Adachi, K. New method for trifluoromethylation of enolate anions and applications to regio-, diastereo- and enantioselective trifluoromethylation. J. Org. Chem. 59, 5692-5699 (1994).
81. Kawai, H., Kusuda, A., Nakamura, S., Shiro, M. & Shibata, N. Catalytic enantioselective trifluoromethylation of azomethine imines with trimethyl(trifluoromethyl)silane. Angew. Chem. Int. Edn 48, 6324-6327 (2009).
82. Hintermann, L. & Togni, A. Catalytic enantioselective fluorination of b-ketoesters. Angew. Chem. Int. Edn 39, 4359-4362 (2000).
83. Hamashima, Y., Yagi, K., Takano, H., Tamás, L. & Sodeoka, M. An efficient enantioselective fluorination of various a-ketoesters catalyzed by chiral palladium complexes. J. Am. Chem. Soc. 124, 14530-14531 (2002). (Pubitemid 35425014)
84. Enders, D. & Hü ttl, M. R. M. Direct organocatalytic a-fluorination of aldehydes and ketones. Synlett 991-993 (2005). (Pubitemid 40524271)
85. Marigo, M., Fielenbach, D., Braunton, A., Kjærsgaard, A. & Jørgensen, K. A. Enantioselective formation of stereogenic carbon-fluorine centers by a simple catalytic method. Angew. Chem. Int. Edn 44, 3703-3706 (2005). (Pubitemid 40817183)
86. Steiner, D. D., Mase, N. & Barbas, C. F. III. Direct asymmetric a-fluorination of aldehydes. Angew. Chem. Int. Edn 44, 3706-3710 (2005).
87. Beeson, T. D. & MacMillan, D. W. C. Enantioselective organocatalytic a-fluorination of aldehydes. J. Am. Chem. Soc. 127, 8826-8828 (2005).
88. Ishimaru, T. et al. Cinchona alkaloid catalyzed enantioselective fluorination of allyl silanes, silyl enol ethers, and oxindoles. Angew. Chem. Int. Edn 47, 4157-4161 (2008).
89. Kwiatkowski, P., Beeson, T. D., Conrad, J. C. & MacMillan, D. W. C. Enantioselective organocatalytic a-fluorinationof cyclic ketones. J.Am.Chem. Soc.133,1738-1741 (2011).
90. Hollingworth, C. et al. Palladium-catalyzed allylic fluorination. Angew. Chem. Int. Edn 50, 2613-2617 (2011).
91. Katcher, M. H. & Doyle, A. G. Palladium-catalyzed asymmetric synthesis of allylic fluorides. J. Am. Chem. Soc. 132, 17402-17404 (2010).
92. Eisenberger, P., Gischig, S. & Togni, A. Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation. Chem. Eur. J. 12, 2579-2586 (2006).
93. Allen, A. E. & MacMillan, D. W. C. The productive merger of iodonium salts and organocatalysis: a non-photolytic approach to the enantioselective a-trifluoromethylation of aldehydes. J. Am. Chem. Soc. 132, 4986-4987 (2010).
94. Beeson, T. D., Mastracchio, A., Hong, J., Ashton, K. & MacMillan, D. W. C. Enantioselective organocatalysis using SOMO activation. Science 316, 582-585 (2007). (Pubitemid 46683140)
95. Nagib, D. A., Scott, M. E. & MacMillan, D. W. C. Enantioselective a-trifluoromethylation of aldehydes via photoredox organocatalysis. J. Am. Chem. Soc. 131, 10875-10877 (2009).
96. Wu, X.-F.,Anbarasan, P.,Neumann, H.& Beller, M. Fromnoblemetal toNobel Prize: palladium-catalyzed coupling reactions as key methods in organic synthesis. Angew. Chem. Int. Edn 49, 9047-9050 (2010).
97. deMeijere, A.& Diederich, F. (eds)Metal-Catalyzed Cross-Coupling Reactions (Wiley, 2004).
98. Hartwig, J. F. Carbon-heteroatom bond-forming reductive elimination of amines, ethers, and sulfides. Acc. Chem. Res. 31, 852-860 (1998). (Pubitemid 128473636)
99. Hartwig, J. F. Carbon-heteroatom bond formation catalysed by organometallic complexes. Nature 455, 314-322 (2008).
100. Muci, A. R. & Buchwald, S. L. in Topics in Current Chemistry Vol. 219 (ed. Miyaura, N.) 131-209 (Springer, 2001).