Visible-light-promoted stereoselective alkylation by combining heterogeneous photocatalysis with organocatalysis

Angewandte Chemie - International Edition

Volumn 51, Issue 17, 2012, Pages 4062-4066

  Cherevatskaya, Maria ^a   Neumann, Matthias ^a   Füldner, Stefan ^a   Harlander, Christoph ^a   Kümmel, Susanne ^a   Dankesreiter, Stephan ^a   Pfitzner, Arno ^a   Zeitler, Kirsten ^a   König, Burkhard ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

alkylation; organocatalysis; photocatalysis; semiconductors; visible light

Indexed keywords

CARBON-CARBON BOND; COVALENT IMMOBILIZATION; HETEROGENEOUS PHOTOCATALYSIS; INORGANIC SEMICONDUCTORS; ORGANOCATALYSIS; ORGANOCATALYSTS; PHOTO-CATALYTIC; STEREO-SELECTIVE; VISIBLE LIGHT;

ALKYLATION; RATE CONSTANTS; REACTION KINETICS; SEMICONDUCTOR MATERIALS; STEREOSELECTIVITY;

PHOTOCATALYSIS;

EID: 84859937539     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201108721     Document Type: Article

References (88)

1. A. J. Bard, Science 1980, 207, 139-144
2. F. Teplý, Collect. Czech. Chem. Commun. 2011, 76, 859-917
3. G. Pandey, M. K. Ghorai, S. Hazra, Pure Appl. Chem. 1996, 68, 653.
4. J. M. R. Narayanam, C. R. J. Stephenson, Chem. Soc. Rev. 2011, 40, 102-113
5. T. P. Yoon, M. A. Ischay, J. Du, Nat. Chem. 2010, 2, 527-532
6. K. Zeitler, Angew. Chem. 2009, 121, 9969-9974
7. Angew. Chem. Int. Ed. 2009, 48, 9785-9789.
8. C. Dai, J. M. R. Narayanam, C. R. J. Stephenson, Nat. Chem. 2011, 3, 140-145.
9. M. A. Ischay, M. E. Anzovino, J. Du, T. P. Yoon, J. Am. Chem. Soc. 2008, 130, 12886-12887
10. J. Du, T. P. Yoon, J. Am. Chem. Soc. 2009, 131, 14604-14605
11. M. A. Ischay, Z. Lu, T. P. Yoon, J. Am. Chem. Soc. 2010, 132, 8572-8574
12. J. Du, L. RuizEspelt, I. A. Guzei, T. P. Yoon, Chem. Sci. 2011, 2, 2115-2119.
13. Z. Lu, M. Shen, T. P. Yoon, J. Am. Chem. Soc. 2011, 133, 1162-1164
14. Y.-Q. Zou, L.-Q. Lu, L. Fu, N.-J. Chang, J. Rong, J.-R. Chen, W.-J. Xiao, Angew. Chem. 2011, 123, 7309-7313
15. Angew. Chem. Int. Ed. 2011, 50, 7171-7175
16. M. Rueping, D. Leonori, T. Poisson, Chem. Commun. 2011, 47, 9615-9617
17. S. Maity, M. Zhu, R. S. Shinabery, N. Zheng, Angew. Chem. 2012, 124, 226-230
18. Angew. Chem. Int. Ed. 2012, 51, 222-226.
19. A. E. Hurtley, M. A. Cismesia, Mi. A. Ischay, T. P. Yoon, Tetrahedron 2011, 67, 4442-4448
20. S. Lin, M. A. Ischay, C. G. Fry, T. P. Yoon, J. Am. Chem. Soc. 2011, 133, 19350-19353.
21. L. Furst, B. S. Matsuura, J. M. R. Narayanam, J. W. Tucker, C. R. J. Stephenson, Org. Lett. 2010, 12, 3104-3107
22. P. V. Pham, D. A. Nagib, D. W. C. MacMillan, Angew. Chem. 2011, 123, 6243-6246
23. Angew. Chem. Int. Ed. 2011, 50, 6119-6122
24. J. D. Nguyen, J. W. Tucker, M. D. Konieczynska, C. R. J. Stephenson, J. Am. Chem. Soc. 2011, 133, 4160-4163
25. M. Rueping, S. Zhu, R. M. Koenigs, Chem. Commun. 2011, 47, 12709-12711
26. A. McNally, C. K. Prier, D. W. C. MacMillan, Science 2011, 334, 114-117
27. D. Kalyani, K. B. McMurtrey, S. R. Neufeldt, M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 18566
28. D. A. Nagib, D. W. C. MacMillan, Nature 2011, 480, 224-228.
29. D. P. Hari, B. König, Org. Lett. 2011, 13, 3852-3855
30. M. Rueping, S. Zhu, R. M. Koenigs, Chem. Commun. 2011, 47, 8679-8681. For the formation of C S bonds, see
31. Y. Cheng, J. Yang, Y. Qu, P. Li, Org. Lett. 2011, 14, 98-101. For the formation of C N bonds, see
32. J. Xuan, Y. Cheng, J. An, L.-Q. Lu, X.-X. Zhang, W.-J. Xiao, Chem. Commun. 2011, 47, 8337-8339.
33. D. A. Nicewicz, D. W. C. MacMillan, Science 2008, 322, 77-80
34. D. A. Nagib, M. E. Scott, D. W. C. MacMillan, J. Am. Chem. Soc. 2009, 131, 10875-10877
35. H.-W. Shih, M. N. VanderWal, R. L. Grange, D. W. C. MacMillan, J. Am. Chem. Soc. 2010, 132, 13600-13603
36. M. Neumann, S. Füldner, B. König, K. Zeitler, Angew. Chem. 2011, 123, 981-985
37. Angew. Chem. Int. Ed. 2011, 50, 951-954.
38. A. Bauer, F. Westkämper, S. Grimme, T. Bach, Nature 2005, 436, 1139-1140
39. C. Müller, A. Bauer, M. M. Maturi, M. C. Cuquerella, M. A. Miranda, T. Bach, J. Am. Chem. Soc. 2011, 133, 16689-16697. For a review on enantioselective photocatalysis using hydrogen-bonding templates, see
40. C. Müller, T. Bach, Aust. J. Chem. 2008, 61, 557-564.
41. A. Atyaoui, L. Bousselmi, H. Cachet, P. Pu, E. M. M. Sutter, J. Photochem. Photobiol. A 2011, 224, 71-79
42. F. Spadavecchia, G. Cappelletti, S. Ardizzone, C. L. Bianchi, S. Cappelli, C. Oliva, P. Scardi, M. Leoni, P. Fermo, Appl. Catal. B 2010, 96, 314-322
43. M. K. Seery, R. George, P. Floris, S. C. Pillai, J. Photochem. Photobiol. A 2007, 189, 258-263
44. J. Tang, J. Ye, Angew. Chem. 2004, 116, 4563-4566
45. Angew. Chem. Int. Ed. 2004, 43, 4463-4466.
46. X. Chen, S. S. Mao, Chem. Rev. 2007, 107, 2891-2959
47. R. M. NavarroYerga, M. C. Álvarez-Galván, F. delValle, J. A. VilloriadeLaMano, J. L. G. Fierro, ChemSusChem 2009, 2, 471-485
48. H. Xu, R. Q. Zhang, A. N. C. Ng, A. B. Djurišić, H. T. Chan, W. K. Chan, S. Y. Tong, J. Phys. Chem. C 2011, 115, 19710-19715
49. M. Antoniadou, V. M. Daskalaki, N. Balis, D. I. Kondarides, C. Kordulis, P. Lianos, Appl. Catal. B 2011, 107, 188-196.
50. H. Kisch, W. Schindler, J. Photochem. Photobiol. A 1993, 103, 257-264
51. H. Kisch, W. Linder, Chem. Unserer Zeit 2001, 35, 250-257
52. M. Gärtner, H. Kisch, Photochem. Photobiol. Sci. 2007, 6, 159-164
53. N. Zeug, J. Bücheler, H. Kisch, J. Am. Chem. Soc. 1985, 107, 1459-1465
54. W. Hetterich, H. Kisch, Chem. Ber. 1987, 121, 15-20.
55. L. Cermenati, C. Richter, A. Albini, Chem. Commun. 1998, 805-806.
56. Z. Xie, C. Wang, K. E. deKrafft, W. Lin, J. Am. Chem. Soc. 2011, 133, 2056-2059
57. C. Wang, Z. Xie, K. E. deKrafft, W. Lin, J. Am. Chem. Soc. 2011, 133, 13445-13454.
58. F. Su, S. C. Mathew, L. Möhlmann, M. Antonietti, X. Wang, S. Blechert, Angew. Chem. 2011, 123, 683-686
59. Angew. Chem. Int. Ed. 2011, 50, 657-660
60. F. Su, S. C. Mathew, G. Lipner, X. Fu, M. Antonietti, S. Blechert, X. Wang, J. Am. Chem. Soc. 2010, 132, 16299-16301.
61. S. Bertelsen, K. A. Jørgensen, Chem. Soc. Rev. 2009, 38, 2178-2189
62. B. List, Top. Curr. Chem. 2010, 291, 1-456 (Asymmetric Organocatalysis)
63. Chem. Rev. 2007, 107, 5413-5883 (special issue on organocatalysis).
64. 2 photocatalyis, see:, X.-H. Ho, M.-J. Kang, S.-J. Kim, E. D. Park, H.-Y. Jang, Catal. Sci. Technol. 2011, 1, 923-926.
65. P25 Degussa with an anatase/rutile ratio of 80:20 was used.
66. P. Roy, S. Berger, P. Schmuki, Angew. Chem. 2011, 123, 2956-2995
67. Angew. Chem. Int. Ed. 2011, 50, 2904-2939
68. S. Higashimoto, N. Kitao, N. Yoshida, T. Sakura, M. Azuma, H. Ohue, Y. Sakata, J. Catal. 2009, 266, 279-285
69. 2.
70. S. U. M. Khan, M. Al-Shahry, W. B. Ingler, Jr., Science 2002, 297, 2243-2245
71. X. Chen, L. Liu, P. Y. Yu, S. S. Maol, Science 2011, 331, 746-750.
72. S. Füldner, R. Mild, H. I. Siegmund, J. A. Schroeder, M. Gruber, B. König, Green Chem. 2010, 12, 400-406.
73. L. Xiong, F. Yang, L. Yan, N. Yan, X. Yang, M. Qiu, Y. Yu, J. Phys. Chem. Solids 2011, 72, 1104-1109.
74. D. Chatterjee, V. R. Patnama, A. Sikdar, P. Joshi, R. Misra, N. N. Rao, J. Hazard. Mater. 2008, 156, 435-441.
75. A. Pfitzner, P. Pohla, Z. Anorg. Allg. Chem. 2009, 635, 1157-1159.
76. M. Hopfner, H. Weiss, D. Meissner, F. W. Heinemann, H. Kisch, Photochem. Photobiol. Sci. 2002, 1, 696-703.
77. Procedure according to ref.[9a]; for details please see the Supporting Information.
78. H. Kisch, Adv. Photochem. 2001, 26, 93-143.
79. For the redox potential of Texas-Red, see:, M. Torimura, S. Kurata, K. Yamada, T. Yokumaku, Y. Kamagata, T. Kanagawa, R. Kurane, Anal. Sci. 2001, 17, 155-160.
80. C.-J. Li, Acc. Chem. Res. 2009, 42, 335-344
81. C. J. Scheuermann, Chem. Asian J. 2010, 5, 436-451
82. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215-1292.
83. A. G. Condie, J.-C. González-Gómez, C. R. J. Stephenson, J. Am. Chem. Soc. 2010, 132, 1464
84. M. Rueping, C. Vila, R. M. Koenigs, K. Poscharny, D. C. Fabry, Chem. Commun. 2011, 47, 2360-2362.
85. Y. Pan, C. W. Kee, L. Chen, C.-H. Tan, Green Chem. 2011, 13, 2682-2685
86. Y. Pan, S. Wang, C. W. Kee, E. Dubuisson, Y. Yang, K. P. Loh, C.-H. Tan, Green Chem. 2011, 13, 3341-3344.
87. Klussmann etal. reported the slow racemization of the products under their oxidative reaction conditions:, A. Sud, D. Sureshkumarz, M. Klussmann, Chem. Commun. 2009, 3169-3171. Our stereochemical analysis also reveals only low ee values as similarly noted in previous reports by Rueping (see Ref.[32b]) and Tan (see Ref.[33a]).
88. For a recent paper on the calculation of flat band potentials of semiconductor oxides, see:, M. C. Toroker, D. K. Kanan, N. Alidoust, L. Y. Isseroff, P. Liaob, E. A. Carter, Phys. Chem. Chem. Phys. 2011, 13, 16644-16654.