Copper-boxmi complexes as highly enantioselective catalysts for electrophilic trifluoromethylthiolations

Chemistry - A European Journal

Volumn 20, Issue 1, 2014, Pages 93-97

  Deng, Qing Hai ^a   Rettenmeier, Christoph ^b   Wadepohl, Hubert ^b   Gade, Lutz H ^a,b  

^a Catalysis Research Laboratory   (Germany)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

ketoesters; asymmetric catalysis; copper; pincer ligands; trifluoromethylthiolation

Indexed keywords

ASYMMETRIC CATALYSIS; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE; ENANTIOSELECTIVE CATALYSTS; KETO ESTER; PINCER LIGANDS; QUATERNARY STEREOCENTERS; TRIFLUOROMETHYLTHIOLATION;

CATALYSTS; ENANTIOMERS; ENANTIOSELECTIVITY;

COPPER;

2 IODYLBENZOIC ACID; 2-IODOXYBENZOIC ACID; COORDINATION COMPOUND; COPPER; ESTER; IODOBENZOIC ACID DERIVATIVE; KETONE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMISTRY; CONFORMATION; PINCER LIGANDS; STEREOISOMERISM; TRIFLUOROMETHYLTHIOLATION; X RAY CRYSTALLOGRAPHY; Β-KETOESTERS;

ASYMMETRIC CATALYSIS; COPPER; PINCER LIGANDS; TRIFLUOROMETHYLTHIOLATION; Β-KETOESTERS;

CATALYSIS; COORDINATION COMPLEXES; COPPER; CRYSTALLOGRAPHY, X-RAY; ESTERS; IODOBENZOATES; KETONES; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 84891495010     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201303641     Document Type: Article

References (78)

1. Bioorganic and Medicinal Chemistry of Fluorine (Eds.:, J.-P. Bégué, D. Bonnet-Delpon,), Wiley-VCH, Hoboken, 2008
2. Organofluorine Chemistry (Ed.:, K. Uneyama,), Blackwell, Oxford, 2006
3. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications (Ed.:, P. Kirsch,), Wiley-VCH, Weinheim, 2004
4. Organofluorine Compounds: Chemistry and Properties (Ed.:, T. Hiyama,), Springer, Berlin, 2000
5. Fluorinated Bio-active Compounds (Eds.:, B. R. Langlois, T. Billard, S. Large, N. Roques,), Fluorine Technology Lyd., Cheshire, 1999
6. Inventory of Industrial Fluoro-Biochemicals (Ed.:, A. Becker,), Eyrolles, Paris, 1996
7. F. Leroux, P. Jeschke, M. Schlosser, Chem. Rev. 2005, 105, 827
8. J. Stetter, F. Lieb, Angew. Chem. 2000, 112, 1792
9. Angew. Chem. Int. Ed. 2000, 39, 1724.
10. C. Hansch, A. Leo, R. W. Taft, Chem. Rev. 1991, 91, 165
11. C. Hansch, A. Leo, S. H. Unger, K. H. Kim, D. Nikaitani, E. J. Lien, J. Med. Chem. 1973, 16, 1207
12. A. Leo, C. Hansch, D. Elkins, Chem. Rev. 1971, 71, 525.
13. V. N. Boiko, Beilstein J. Org. Chem. 2010, 6, 880
14. B. Manteau, S. Pazenok, J.-P. Vors, F. R. Leroux, J. Fluorine Chem. 2010, 131, 140.
15. J. M. Kremsner, M. Rack, C. Pilger, C. Oliver Kappe, Tetrahedron Lett. 2009, 50, 3665
16. L. Saint-Jalmes, J. Fluorine Chem. 2006, 127, 85
17. E. A. Nodiff, S. Lipschutz, P. N. Craig, M. Gordon, J. Org. Chem. 1960, 25, 60.
18. A. Harsányi, É. Dorkõ, Á. Csapõ, T. Bakõ, C. Peltz, J. Rábai, J. Fluorine Chem. 2011, 132, 1241
19. I. Kieltsch, P. Eisenberger, A. Togni, Angew. Chem. 2007, 119, 768
20. Angew. Chem. Int. Ed. 2007, 46, 754
21. C. Pooput, M. Medebielle, W. R. Dolbier, Org. Lett. 2004, 6, 301
22. S. Large, N. Roques, B. R. Langlois, J. Org. Chem. 2000, 65, 8848
23. B. Quiclet-Sire, R. N. Saicic, S. Z. Zars, Tetrahedron Lett. 1996, 37, 9057
24. T. Umemoto, S. Ishihara, J. Am. Chem. Soc. 1993, 115, 2156
25. V. G. Koshechko, L. A. Kiprianova, L. I. Fileleeva, Tetrahedron Lett. 1992, 33, 6677
26. V. Soloshonok, V. Kukhar, Y. Pastrait, V. Nazaretian, Synlett 1992, 657.
27. Review:, A. Tlili, T. Billard, Angew. Chem. 2013, 125, 6952
28. Angew. Chem. Int. Ed. 2013, 52, 6818.
29. S. Braverman, E. V. K. Suresh Kumar, M. Cherkinsky, M. Sprecher, I. Goldberg, Tetrahedron 2005, 61, 3547
30. S. Munavalli, D. K. Rohrbaugh, D. I. Rossman, F. J. Berg, G. W. Wagner, H. D. Durst, Synth. Commun. 2000, 30, 2847
31. A. Haas, U. Niemann, Chem. Ber. 1977, 110, 67
32. A. Haas, V. Hellwig, J. Fluorine Chem. 1975, 6, 521
33. S. Andreades, J. F. Harris, W. A. Sheppard, J. Org. Chem. 1964, 29, 898
34. J. F. Harris, J. Am. Chem. Soc. 1962, 84, 3148.
35. J. H. Clark, C. W. Jones, A. P. Kybett, M. A. McClinton, J. M. Miller, D. Bishop, R. J. Blade, J. Fluorine Chem. 1990, 48, 249
36. A. Haas, H.-U. Krächter, Chem. Ber. 1988, 121, 1833
37. L. M. Yagupolskii, N. V. Kondratenko, V. P. Sambur, Synthesis 1975, 721.
38. J. Liu, L. Chu, F.-L. Qing, Org. Lett. 2013, 15, 894
39. Y. Yang, X. Jiang, F.-L. Qing, J. Org. Chem. 2012, 77, 7538
40. A. Ferry, T. Billard, E. Bacqué, B. R. Langlois, J. Fluorine Chem. 2012, 134, 160
41. F. Baert, J. Colomb, T. Billard, Angew. Chem. 2012, 124, 10528
42. Angew. Chem. Int. Ed. 2012, 51, 10382
43. A. Ferry, T. Billard, B. R. Langlois, E. Bacqué, Angew. Chem. 2009, 121, 8703
44. Angew. Chem. Int. Ed. 2009, 48, 8551.
45. K.-P. Wang, S. Y. Yun, P. Mamidipalli, D. Lee, Chem. Sci. 2013, 4, 3205
46. G. Teverovskiy, D. S. Surry, S. L. Buchwald, Angew. Chem. 2011, 123, 7450
47. Angew. Chem. Int. Ed. 2011, 50, 7312
48. D. J. Adams, J. H. Clark, J. Org. Chem. 2000, 65, 1456.
49. C.-P. Zhang, D. A. Vicic, Chem. Asian J. 2012, 7, 1756
50. C.-P. Zhang, D. A. Vicic, J. Am. Chem. Soc. 2012, 134, 183.
51. L. D. Tran, I. Popov, O. Daugulis, J. Am. Chem. Soc. 2012, 134, 18237
52. A. A. Kolomeitsev, K. Yu. Chabanenko, G.-V. Röschenthaler, Y. L. Yagupolskii, Synthesis 1994, 145.
53. D. Kong, Z. Jiang, S. Xin, Z. Bai, Y. Yuan, Z. Weng, Tetrahedron 2013, 69, 6046
54. Z. Weng, W. He, C. Chen, R. Lee, D. Tan, Z. Lai, D. Kong, Y. Yuan, K.-W. Huang, Angew. Chem. 2013, 125, 1588
55. Angew. Chem. Int. Ed. 2013, 52, 1548.
56. Y.-D. Yang, A. Azuma, E. Tokunaga, M. Yamasaki, M. Shiro, N. Shibata, J. Am. Chem. Soc. 2013, 135, 8782
57. C. Chen, Y. Xie, L. Chu, R.-W. Wang, X. Zhang, F.-L. Qing, Angew. Chem. 2012, 124, 2542
58. Angew. Chem. Int. Ed. 2012, 51, 2492
59. C. Chen, L. Chu, F.-L. Qing, J. Am. Chem. Soc. 2012, 134, 12454
60. Q.-Y. Chen, J.-X. Duan, J. Chem. Soc. Chem. Commun. 1993, 918.
61. X. Shao, X. Wang, T. Yang, L. Lu, Q. Shen, Angew. Chem. 2013, 125, 3541
62. Angew. Chem. Int. Ed. 2013, 52, 3457.
63. X. Wang, T. Yang, X. Cheng, Q. Shen, Angew. Chem. 2013, 125, 13098
64. Angew. Chem. Int. Ed. 2013, 52, 12860. Another organocatalytic method has since been published by
65. T. Bootwicha, X. Liu, R. Pluta, I. Atodiresei, M. Rueping, Angew. Chem. 2013, 125, 13093
66. Angew. Chem. Int. Ed. 2013, 52, 12856.
67. Q.-H. Deng, H. Wadepohl, L. H. Gade, Chem. Eur. J. 2011, 17, 14922
68. Q.-H. Deng, H. Wadepohl, L. H. Gade, J. Am. Chem. Soc. 2012, 134, 2946
69. Q.-H. Deng, H. Wadepohl, L. H. Gade, J. Am. Chem. Soc. 2012, 134, 10769
70. Q.-H. Deng, T. Bleith, H. Wadepohl, L. H. Gade, J. Am. Chem. Soc. 2013, 135, 5356.
71. P. Eisenberger, S. Gischig, A. Togni, Chem. Eur. J. 2006, 12, 2579.
72. V. V. Zhdankin, A. P. Krasutsky, C. J. Kuehl, A. J. Simonsen, J. K. Woodward, B. Mismash, J. T. Bolz, J. Am. Chem. Soc. 1996, 118, 5192
73. S. Akai, T. Okuno, T. Takada, H. Tohma, Y. Kita, Heterocycles 1996, 42, 47.
74. Details of the crystal structure determinations are given in the Supporting Information. CCDC-<960246 (6 b) and CCDC-960247 (8) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
75. V. Justribõ, S. C. Pellegrinet, M. I. Colombo, J. Org. Chem. 2007, 72, 3702
76. A. Ivkovic, R. Matovic, R. N. Saicic, Org. Lett. 2004, 6, 1221
77. K. V. Emelen, T. D. Wit, G. J. Hoornaert, F. Compernolle, Org. Lett. 2000, 2, 3083
78. G. A. Molander, C. R. Harris, J. Am. Chem. Soc. 1995, 117, 3705.