Multicomponent Oxyalkylation of Styrenes Enabled by Hydrogen-Bond-Assisted Photoinduced Electron Transfer

Angewandte Chemie - International Edition

Volumn 56, Issue 13, 2017, Pages 3708-3711

  Tlahuext Aca, Adrian ^a   Garza Sanchez, R Aleyda ^a   Glorius, Frank ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

alkyl radicals; decarboxylation; hydrogen bonding; oxyalkylation; photoredox catalysis

Indexed keywords

CARBOXYLATION; CHEMICAL ACTIVATION; ELECTRON TRANSITIONS; FREE RADICAL REACTIONS; SCAFFOLDS; STYRENE;

ALKYL RADICALS; COMPLEX ALCOHOL; DECARBOXYLATION; MULTICOMPONENTS; OXYALKYLATION; PHOTO-INDUCED ELECTRON TRANSFER; PHOTOREDOX CATALYSIS; STYRENE MOIETY;

HYDROGEN BONDS;

EID: 85013455450     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201700049     Document Type: Article

References (78)

1. Selected reviews:
2. T. P. Yoon, M. A. Ischay, J. Du, Nat. Chem. 2010, 2, 527;
3. J. M. R. Narayanam, C. R. J. Stephenson, Chem. Soc. Rev. 2011, 40, 102;
4. J. Xuan, W.-J. Xiao, Angew. Chem. Int. Ed. 2012, 51, 6828;
5. Angew. Chem. 2012, 124, 6934;
6. C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev. 2013, 113, 5322;
7. D. M. Schultz, T. P. Yoon, Science 2014, 343, 1239176;
8. M. N. Hopkinson, B. Sahoo, J.-L. Li, F. Glorius, Chem. Eur. J. 2014, 20, 3874;
9. D. M. Arias-Rotondo, J. K. McCusker, Chem. Soc. Rev. 2016, 45, 5803.
10. Selected examples:
11. Y. Miyake, K. Nakajima, Y. Nishibayashi, Chem. Commun. 2013, 49, 7854;
12. L. Chen, C. S. Chao, Y. Pan, S. Dong, Y. C. Teo, J. Wang, C.-H. Tan, Org. Biomol. Chem. 2013, 11, 5922;
13. C. Cassani, G. Bergonzini, C.-J. Wallentin, Org. Lett. 2014, 16, 4228;
14. Z. Zuo, D. W. C. MacMillan, J. Am. Chem. Soc. 2014, 136, 5257;
15. L. Chu, C. Ohta, Z. Zuo, D. W. C. MacMillan, J. Am. Chem. Soc. 2014, 136, 10886;
16. A. Noble, D. W. C. MacMillan, J. Am. Chem. Soc. 2014, 136, 11602;
17. Q.-Q. Zhou, W. Guo, W. Ding, X. Wu, X. Chen, L.-Q. Lu, W.-J. Xiao, Angew. Chem. Int. Ed. 2015, 54, 11196;
18. Angew. Chem. 2015, 127, 11348;
19. S. Ventre, F. R. Petronijevic, D. W. C. MacMillan, J. Am. Chem. Soc. 2015, 137, 5654;
20. C. C. Nawrat, C. R. Jamison, Y. Slutskyy, D. W. C. MacMillan, L. E. Overman, J. Am. Chem. Soc. 2015, 137, 11270;
21. J. D. Griffin, M. A. Zeller, D. A. Nicewicz, J. Am. Chem. Soc. 2015, 137, 11340;
22. L. Candish, E. A. Standley, A. Gómez-Suárez, S. Mukherjee, F. Glorius, Chem. Eur. J. 2016, 22, 9971;
23. L. Candish, L. Pitzer, A. Gómez-Suárez, F. Glorius, Chem. Eur. J. 2016, 22, 4753;
24. A. Millet, Q. Lefebvre, M. Rueping, Chem. Eur. J. 2016, 22, 13464;
25. F. Le Vaillant, T. Courant, J. Waser, Angew. Chem. Int. Ed. 2015, 54, 11200;
26. Angew. Chem. 2015, 127, 11352;
27. J. Xuan, Z.-G. Zhang, W.-J. Xiao, Angew. Chem. Int. Ed. 2015, 54, 15632;
28. Angew. Chem. 2015, 127, 15854.
29. G. Bergonzini, C. Cassani, C.-J. Wallentin, Angew. Chem. Int. Ed. 2015, 54, 14066;
30. Angew. Chem. 2015, 127, 14272;
31. J. W. Beatty, J. J. Douglas, K. P. Cole, C. R. J. Stephenson, Nat. Commun. 2015, 6, 7919;
32. J. W. Beatty, J. J. Douglas, R. Miller, R. C. McAtee, K. P. Cole, C. R. J. Stephenson, Chem. 2016, 1, 456.
33. K. Okada, K. Okamoto, N. Morita, K. Okubo, M. Oda, J. Am. Chem. Soc. 1991, 113, 9401;
34. K. Okada, K. Okubo, N. Morita, M. Oda, Tetrahedron Lett. 1992, 33, 7377;
35. K. Okada, K. Okubo, N. Morita, M. Oda, Chem. Lett. 1993, 22, 2021.
36. K. Okada, K. Okamoto, M. Oda, J. Am. Chem. Soc. 1988, 110, 8736.
37. M. J. Schnermann, L. E. Overman, Angew. Chem. Int. Ed. 2012, 51, 9576;
38. Angew. Chem. 2012, 124, 9714;
39. G. L. Lackner, K. W. Quasdorf, L. E. Overman, J. Am. Chem. Soc. 2013, 135, 15342;
40. G. Pratsch, G. L. Lackner, L. E. Overman, J. Org. Chem. 2015, 80, 6025;
41. J. Yang, J. Zhang, L. Qi, C. Hu, Y. Chen, Chem. Commun. 2015, 51, 5275;
42. D. J. Tao, Y. Slutskyy, L. E. Overman, J. Am. Chem. Soc. 2016, 138, 2186;
43. M. Jiang, H. Yang, H. Fu, Org. Lett. 2016, 18, 1968;
44. C. R. Jamison, L. E. Overman, Acc. Chem. Res. 2016, 49, 1578;
45. Y. Slutskyy, C. R. Jamison, G. L. Lackner, D. S. Müller, A. P. Dieskau, N. L. Untiedt, L. E. Overman, J. Org. Chem. 2016, 81, 7029;
46. J. Li, H. Tian, M. Jiang, H. Yang, Y. Zhao, H. Fu, Chem. Commun. 2016, 52, 8862;
47. J. Schwarz, B. König, Green Chem. 2016, 18, 4743.
48. Reiser and co-workers have reported the only visible-light-promoted decarboxylative fragmentation using N-(acyloxy)phthalimides under redox-neutral conditions. Although more studies are required, evidence provided by the authors pointed to a triplet sensitization mechanism: G. Kachkovskyi, C. Faderl, O. Reiser, Adv. Synth. Catal. 2013, 355, 2240.
49. M. Oelgemöller, A. G. Griesbeck, J. Lex, A. Haeuseler, M. Schmittel, M. Niki, D. Hesek, Y. Inoue, Org. Lett. 2001, 3, 1593;
50. M. Oelgemoeller, A. Haeuseler, M. Schmittel, A. G. Griesbeck, J. Lex, Y. Inoue, J. Chem. Soc. Perkin Trans. 2 2002, 676.
51. Examples of hydrogen bonding in visible-light-mediated photocatalysis:
52. J. L. Jeffrey, J. A. Terrett, D. W. C. MacMillan, Science 2015, 349, 1532;
53. K. T. Tarantino, P. Liu, R. R. Knowles, J. Am. Chem. Soc. 2013, 135, 10022;
54. L. J. Rono, H. G. Yayla, D. Y. Wang, M. F. Armstrong, R. R. Knowles, J. Am. Chem. Soc. 2013, 135, 17735;
55. E. C. Gentry, R. R. Knowles, Acc. Chem. Res. 2016, 49, 1546.
56. H. Egami, R. Shimizu, M. Sodeoka, Tetrahedron Lett. 2012, 53, 5503;
57. Y. Yasu, T. Koike, M. Akita, Angew. Chem. Int. Ed. 2012, 51, 9567;
58. Angew. Chem. 2012, 124, 9705;
59. Y. Li, A. Studer, Angew. Chem. Int. Ed. 2012, 51, 8221;
60. Angew. Chem. 2012, 124, 8345;
61. P. G. Janson, I. Ghoneim, N. O. Ilchenko, K. Szabó, Org. Lett. 2012, 14, 2882.
62. M. R. Heinrich, A. Wetzel, M. Kirschstein, Org. Lett. 2007, 9, 3833;
63. M. Hartmann, Y. Li, A. Studer, J. Am. Chem. Soc. 2012, 134, 16516;
64. G. Fumagalli, S. Boyd, M. F. Greaney, Org. Lett. 2013, 15, 4398;
65. W. Guo, H.-G. Cheng, L.-Y. Chen, J. Xuan, Z.-J. Feng, J.-R. Chen, L.-Q. Lu, W.-J. Xiao, Adv. Synth. Catal. 2014, 356, 2787;
66. M. R. Heinrich, Chem. Eur. J. 2009, 15, 820.
67. Y. Nobe, K. Arayama, H. Urabe, J. Am. Chem. Soc. 2005, 127, 18006;
68. T. H. Graham, C. M. Jones, N. T. Jui, D. W. C. MacMillan, J. Am. Chem. Soc. 2008, 130, 16494;
69. Y. Wang, L. Zhang, Y. Yang, P. Zhang, Z. Du, C. Wang, J. Am. Chem. Soc. 2013, 135, 18048;
70. H. Yi, X. Zhang, C. Qin, Z. Liao, J. Liu, A. Lei, Adv. Synth. Catal. 2014, 356, 2873;
71. C. Chatalova-Sazepin, Q. Wang, G. M. Sammis, J. Zhu, Angew. Chem. Int. Ed. 2015, 54, 5443;
72. Angew. Chem. 2015, 127, 5533;
73. Z. Liao, H. Yi, Z. Li, C. Fan, X. Zhang, J. Liu, Z. Deng, A. Lei, Chem. Asian J. 2015, 10, 96;
74. W.-T. Wei, H.-B. Li, R.-J. Songa, J.-H. Li, Chem. Commun. 2015, 51, 11325;
75. T. M. Ha, C. Chatalova-Sazepin, Q. Wang, J. Zhu, Angew. Chem. Int. Ed. 2016, 55, 9249;
76. Angew. Chem. 2016, 128, 9395.
77. The hydrogen-bond donor ability of water is greater (1.17) than that of methanol (0.98) based on the α Taft–Kamlet parameter: Y. Marcus, J. Solution Chem. 1991, 20, 929. In assays at fixed concentration of 2 a and variable amounts of water or methanol, we observed a Ksvwater > KsvMeOH. See the Supporting Information for further details.
78. The hydrogen-bond acceptor basicity (β) of DMF and MeCN is 0.69 and 0.40, respectively. See Ref. [13].