Enantioselective, catalytic trichloromethylation through visible-light-activated photoredox catalysis with a chiral iridium complex

Journal of the American Chemical Society

Volumn 137, Issue 30, 2015, Pages 9551-9554

  Huo, Haohua ^a   Wang, Chuanyong ^a   Harms, Klaus ^a   Meggers, Eric ^a,b  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b XIAMEN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY; IRIDIUM; LIGHT;

CHIRAL LEWIS ACID; DUAL FUNCTION; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE; IRIDIUM COMPLEX; PHOTOREDOX CATALYSIS; VISIBLE LIGHT;

IRIDIUM COMPOUNDS;

IMIDAZOLE DERIVATIVE; IRIDIUM COMPLEX; LEWIS ACID; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ELECTRON TRANSPORT; ENANTIOSELECTIVITY; METHYLATION; OXIDATION REDUCTION REACTION; PHOTOSENSITIZATION;

EID: 84938840938     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b06010     Document Type: Article

References (53)

1. Wang, C.; Lu, Z. Org. Chem. Front. 2015, 2, 179-190 10.1039/C4QO00306C
2. Meggers, E. Chem. Commun. 2015, 51, 3290-3301 10.1039/C4CC09268F
3. Brimioulle, R.; Lenhart, D.; Maturi, M. M.; Bach, T. Angew. Chem., Int. Ed. 2015, 54, 3872-3890 10.1002/anie.201411409
4. Peña-López, M.; Rosas-Hernández, A.; Beller, M. Angew. Chem., Int. Ed. 2015, 54, 5006-5008 10.1002/anie.201411513
5. Fagnoni, M.; Dondi, D.; Ravelli, D.; Albini, A. Chem. Rev. 2007, 107, 2725-2756 10.1021/cr068352x
6. Zeitler, K. Angew. Chem., Int. Ed. 2009, 48, 9785-9789 10.1002/anie.200904056
7. Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527-532 10.1038/nchem.687
8. Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102-113 10.1039/B913880N
9. Teplý, F. Collect. Czech. Chem. Commun. 2011, 76, 859-917 10.1135/cccc2011078
10. Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828-6838 10.1002/anie.201200223
11. Shi, L.; Xia, W. Chem. Soc. Rev. 2012, 41, 7687-7697 10.1039/c2cs35203f
12. Ravelli, D.; Fagnoni, M.; Albini, A. Chem. Soc. Rev. 2013, 42, 97-113 10.1039/C2CS35250H
13. Reckenthäler, M.; Griesbeck, A. G. Adv. Synth. Catal. 2013, 355, 2727-2744 10.1002/adsc.201300751
14. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322-5363 10.1021/cr300503r
15. Hari, D. P.; König, B. Angew. Chem., Int. Ed. 2013, 52, 4734-4743 10.1002/anie.201210276
16. Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1239176 10.1126/science.1239176
17. Studer, A.; Curran, D. P. Nat. Chem. 2014, 6, 765-773 10.1038/nchem.2031
18. Zhang, N.; Samanta, S. R.; Rosen, B. M.; Percec, V. Chem. Rev. 2014, 114, 5848-5958 10.1021/cr400689s
19. Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77-80 10.1126/science.1161976
20. Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875-10877 10.1021/ja9053338
21. Neumann, M.; Füldner, S.; König, B.; Zeitler, K. Angew. Chem., Int. Ed. 2011, 50, 951-954 10.1002/anie.201002992
22. DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094-8097 10.1021/ja3030164
23. Cherevatskaya, M.; Neumann, M.; Füldner, S.; Harlander, C.; Kümmel, S.; Dankesreiter, S.; Pfitzner, A.; Zeitler, K.; König, B. Angew. Chem., Int. Ed. 2012, 51, 4062-4066 10.1002/anie.201108721
24. Rono, L. J.; Yayla, H. G.; Wang, D. Y.; Armstrong, M. F.; Knowles, R. R. J. Am. Chem. Soc. 2013, 135, 17735-17738 10.1021/ja4100595
25. Cecere, G.; König, C. M.; Alleva, J. L.; MacMillan, D. W. C. J. Am. Chem. Soc. 2013, 135, 11521-11524 10.1021/ja406181e
26. Bergonzini, G.; Schindler, C. S.; Wallentin, C.-J.; Jacobsen, E. N.; Stephenson, C. R. J. Chem. Sci. 2014, 5, 112-116 10.1039/C3SC52265B
27. Arceo, E.; Jurberg, I. D.; álvarez-Fernández, A.; Melchiorre, P. Nat. Chem. 2013, 5, 750-756 10.1038/nchem.1727
28. Du, J.; Skubi, K. L.; Schultz, D. M.; Yoon, T. P. Science 2014, 344, 392-396 10.1126/science.1251511
29. Tellis, J. C.; Primer, D. N.; Molander, G. A. Science 2014, 345, 433-436 10.1126/science.1253647
30. Zhu, Y.; Zhang, L.; Luo, S. J. Am. Chem. Soc. 2014, 136, 14642-14645 10.1021/ja508605a
31. Gutierrez, O.; Tellis, J. C.; Primer, D. N.; Molander, G. A.; Kozlowski, M. C. J. Am. Chem. Soc. 2015, 137, 4896-4899 10.1021/ja513079r
32. Woźniak, Ł.; Murphy, J. J.; Melchiorre, P. J. Am. Chem. Soc. 2015, 137, 5678-5681 10.1021/jacs.5b03243
33. Silvi, M.; Arceo, E.; Jurberg, I. D.; Cassani, C.; Melchiorre, P. J. Am. Chem. Soc. 2015, 137, 6120-6123 10.1021/jacs.5b01662
34. Huo, H.; Shen, X.; Wang, C.; Zhang, L.; Röse, P.; Chen, L.-A.; Harms, K.; Marsch, M.; Hilt, G.; Meggers, E. Nature 2014, 515, 100-103 10.1038/nature13892
35. For a related discussion, see: Skubi, K. L.; Yoon, T. P. Nature 2014, 515, 45-46 10.1038/515045a
36. Hofheinz, W.; Oberhänsli, W. E. Helv. Chim. Acta 1977, 60, 660-669 10.1002/hlca.19770600238
37. Unson, M. D.; Rose, C. B.; Faulkner, D. J.; Brinen, L. S.; Steiner, J. R.; Clardy, J. J. Org. Chem. 1993, 58, 6336-6343 10.1021/jo00075a029
38. Orjala, J.; Gerwick, W. H. J. Nat. Prod. 1996, 59, 427-430 10.1021/np960085a
39. Fu, X.; Zeng, L.-M.; Su, J.-Y.; Pais, M. J. Nat. Prod. 1997, 60, 695-696 10.1021/np970079u
40. MacMillan, J. B.; Trousdale, E. K.; Molinski, T. F. Org. Lett. 2000, 2, 2721-2723 10.1021/ol006326u
41. Helmchen, G.; Wegner, G. Tetrahedron Lett. 1985, 26, 6047-6050 10.1016/S0040-4039(00)95121-9
42. Brantley, S. E.; Molinski, T. F. Org. Lett. 1999, 1, 2165-2167 10.1021/ol991256g
43. Beaumont, S.; Ilardi, E. A.; Monroe, L. R.; Zakarian, A. J. Am. Chem. Soc. 2010, 132, 1482-1483 10.1021/ja910154f
44. Gu, Z.; Zakarian, A. Angew. Chem., Int. Ed. 2010, 49, 9702-9705 10.1002/anie.201005354
45. Ilardi, E. A.; Zakarian, A. Chem.-Asian J. 2011, 6, 2260-2263 10.1002/asia.201100338
46. Gu, Z.; Herrmann, A. T.; Zakarian, A. Angew. Chem., Int. Ed. 2011, 50, 7136-7139 10.1002/anie.201101364
47. Amatov, T.; Jahn, U. Angew. Chem., Int. Ed. 2011, 50, 4542-4544 10.1002/anie.201007672
48. Herrmann, A. T.; Smith, L. L.; Zakarian, A. J. Am. Chem. Soc. 2012, 134, 6976-6979 10.1021/ja302552e
49. Hori, Y.; Nagano, Y.; Uchiyama, H.; Yamada, Y.; Taniguchi, H. Chem. Lett. 1978, 73-76 10.1246/cl.1978.73
50. Wang, C.; Zheng, Y.; Huo, H.; Röse, P.; Zhang, L.; Harms, K.; Hilt, G.; Meggers, E. Chem.-Eur. J. 2015, 21, 7355-7359 10.1002/chem.201500998
51. Although 2-acyl imidazoles can be converted to a wide variety of carbonyl compounds (e.g. Evans, D. A.; Fandrick, K. R.; Song, H.-J.; Scheidt, K. A.; Xu, R. J. Am. Chem. Soc. 2007, 129, 10029-10041), these methods are not applicable to compounds 2 due to the sensitivity of the CCl3 group towards HCl elimination under basic conditions. See SI for test reactions.
52. Rossi, R. A.; Pierini, A. B.; Peñéñory, A. B. Chem. Rev. 2003, 103, 71-168 10.1021/cr960134o
53. See SI for additional experiments which confirm the significantly stronger coordination of 2-acylpyridines compared their imidazole analogs. For related observations, see also: Shen, X.; Huo, H.; Wang, C.; Zhang, B.; Harms, K.; Meggers, E. Chem.-Eur. J. 2015, 21, 9720-9726 10.1002/chem.201500922