Mild and Low-Pressure fac-Ir(ppy)3-Mediated Radical Aminocarbonylation of Unactivated Alkyl Iodides through Visible-Light Photoredox Catalysis

Chemistry - A European Journal

Volumn 22, Issue 27, 2016, Pages 9155-9161

  Chow, Shiao Y ^a   Stevens, Marc Y ^a   Åkerbladh, Linda ^a   Bergman, Sara ^a   Odell, Luke R ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

amides; carbonylation; photocatalysis; radical reactions

Indexed keywords

AMINES; CARBONYLATION; CATALYSIS; DEHALOGENATION; PHOTOCATALYSIS; REACTION KINETICS;

ALKYL RADICALS; AMINOCARBONYLATION; CHAMBERED SYSTEMS; FACILE PREPARATION; PHOTOREDOX CATALYSIS; RADICAL REACTIONS; REDUCTIVE DEHALOGENATION; VISIBLE LIGHT;

AMIDES;

EID: 84977560511     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201601694     Document Type: Article

References (82)

1. A. Greenberg, C. Breneman, J. Liebman, The Amide Linkage: Structural Significance in Chemistry, Biochemistry and Material Science, Wiley-Interscience, Hoboken, 2003.
2. R. Lanigan, P. Starkovand, T. Sheppard, J. Org. Chem. 2013, 78, 4512–4523.
3. C. Montalbetti, V. Facque, Tetrahedron 2005, 61, 10827–10852.
4. K. Ishihara, S. Ohara, H. Yamamoto, J. Org. Chem. 1996, 61, 4196–4197.
5. R. Al-Zoubi, O. Marion, D. Hall, Angew. Chem. Int. Ed. 2008, 47, 2876–2879;
6. Angew. Chem. 2008, 120, 2918–2921.
7. P. Tang, Org. Synth. 2005, 81, 262–268.
8. J. W. Bode, S. S. Sohn, J. Am. Chem. Soc. 2007, 129, 13798–13799.
9. H. Vora, T. Rovis, J. Am. Chem. Soc. 2007, 129, 13796–13797.
10. S. de Sarkar, A. Studer, Org. Lett. 2010, 12, 1992–1995.
11. W. Bailey, J. Patricia, J. Organomet. Chem. 1988, 352, 1–46.
12. P. Knochel, Angew. Chem. Int. Ed. 2003, 42, 4302–4320;
13. Angew. Chem. 2003, 115, 4438–4456.
14. N. M. Yoon, Pure Appl. Chem. 1996, 68, 843–848.
15. W. P. Neumann, Synthesis 1987, 665–683.
16. J. Sanchez, T. Myers in Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed., Wiley, New York, 2000, pp. 431–460.
17. C. Chatgilialoglu, Acc. Chem. Res. 1992, 25, 188–194.
18. R. Backlin, W. Sherman, J. Chem. Soc. D 1971, 453–454.
19. C. Brancour, T. Fukuyama, Y. Mukai, T. Skrydstrup, I. Ryu, Org. Lett. 2013, 15, 2794–2797;
20. I. Ryu, K. Nagahara, N. Kambe, N. Sonoda, S. Kreimerman, M. Komatsu, Chem. Commun. 1998, 1953–1954.
21. J. Nguyen, E. d′Amato, J. Narayanam, C. Stephenson, Nat. Chem. 2012, 4, 854–859.
22. T. Koike, M. Akita, Inorg. Chem. Front. 2014, 1, 562–576.
23. A. Kwong, R. Kauffman, P. Hurter, P. Mueller, Nat. Biotechnol. 2011, 29, 993–1003.
24. R. Vardanyan, V. Hruby, Fut. Med. Chem. 2014, 6, 385–412.
25. C. Smith, J. Vane, FASEB J. 2003, 17, 788–789.
26. S. P. Webster, P. Ward, M. Binnie, E. Craigie, K. M. M. McConnell, K. Sooy, A. Vinter, J. R. Seckl, B. R. Walker, Bioorg. Med. Chem. Lett. 2007, 17, 2838–2843.
27. G. Gechele, G. Stea, Eur. Polym. J. 1965, 1, 91–102.
28. J. Wannberg, M. Larhed, J. Org. Chem. 2003, 68, 5750–5753.
29. J. R. Martinelli, M. M. Freckmann, S. L. Buchwald, Org. Lett. 2006, 8, 4843–4846.
30. R. Grigg, S. P. Mutton, Tetrahedron 2010, 66, 5515–5548.
31. C. F. J. Barnard, Organometallics 2008, 27, 5402–5422.
32. A. Brennführer, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 2009, 48, 4114–4133;
33. Angew. Chem. 2009, 121, 4176–4196.
34. B. Roberts, L. Liptrot, T. Alcaraz, M. Luker, M. Stocks, Org. Lett. 2010, 12, 4280–4283.
35. W. Ren, M. Yamane, J. Org. Chem. 2010, 75, 8410–8415.
36. L. Wu, X. Fang, Q. Liu, R. Jackstell, M. Beller, X. F. Wu, ACS Catal. 2014, 4, 2977–2989.
37. X. Wu, Y. Zhao, H. Ge, J. Am. Chem. Soc. 2015, 137, 4924–4927.
38. O. Itsenko, T. Kihlberg, B. Långström, J. Org. Chem. 2004, 69, 4356–4360.
39. O. Itsenko, D. Norberg, T. Rasmussen, B. Långström, C. Chatgilialoglu, J. Am. Chem. Soc. 2007, 129, 9020–9031.
40. O. Itsenko, B. Långström, J. Org. Chem. 2005, 70, 2244–2249.
41. S. Sumino, T. Ui, Y. Hamada, T. Fukuyama, I. Ryu, Org. Lett. 2015, 17, 4952–4955.
42. T. Fukuyama, S. Nishitani, T. Inouye, K. Morimoto, I. Ryu, Org. Lett. 2006, 8, 1383–1386.
43. T. Kawamoto, A. Sato, I. Ryu, Chem. Eur. J. 2015, 21, 14764–14767.
44. S. Sumino, A. Fusano, T. Fukuyama, I. Ryu, Synlett 2012, 1331–1334;
45. For a review on carbonylation of saturated alcohols and iodoalkanes, see: I. Ryu, Chem. Soc. Rev. 2001, 30, 16–25.
46. I. Ryu, N. Sonoda, Angew. Chem. Int. Ed. Engl. 1996, 35, 1050–1056;
47. Angew. Chem. 1996, 108, 1140–1157.
48. I. Ryu, T. Fukuyama, M. Tojino, Y. Uenoyama, Y. Yonamine, N. Terasoma, H. Matsubara, Org. Biomol. Chem. 2011, 9, 3780–3786.
49. S. Sumino, A. Fusano, T. Fukuyama, I. Ryu, Acc. Chem. Res. 2014, 47, 1563–1574.
50. A. Studer, D. P. Curran, Angew. Chem. Int. Ed. 2016, 55, 58–102;
51. Angew. Chem. 2016, 128, 58–106.
52. C. Prier, S. Rankic, D. Macmillan, Chem. Rev. 2013, 113, 5322–5363.
53. C. W. Kee, K. M. Chan, M. W. Wong, C.-H. Tan, Asian J. Org. Chem. 2014, 3, 536–544.
54. C. W. Kee, K. F. Chin, M. W. Wong, C.-H. Tan, Chem. Commun. 2014, 50, 8211–8214.
55. V. A. Schmidt, R. K. Quinn, A. T. Brusoe, E. J. Alexanian, J. Am. Chem. Soc. 2014, 136, 14389–14392.
56. P. Nordeman, L. R. Odell, M. Larhed, J. Org. Chem. 2012, 77, 11393–11398.
57. S.-Y. Chow, M. Y. Stevens, L. R. Odell, J. Org. Chem. 2016, 81, 2681–2691.
58. G. Litwinienko, L. Beckwith, K. Ingold, Chem. Soc. Rev. 2011, 40, 2157–2166.
59. C. Jensen, K. Lindsay, R. Taaning, J. Karaffa, A. Hansen, T. Skrydstrup, J. Am. Chem. Soc. 2005, 127, 6544–6545.
60. O. Kurnysheva, N. Gritsanbc, Y. Tsentalovich, Phys. Chem. Chem. Phys. 2001, 3, 3677–3682.
61. A. R. Katritzky, Z. Wang, S. Slavov, M. Tsikolia, D. Dobchev, N. G. Akhmedov, C. D. Hall, U. R. Bernier, G. G. Clark, K. J. Linthicum, Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 7359–7364.
62. J.-M. Gaudin, T. Lander, O. Nikolaenko, Chem. Biodiversity 2008, 5, 617–635.
63. M. G. Vinogradov, G. Nikishin, Russ. Chem. Rev. 1971, 40, 916–932.
64. N. Turro, I. Gould, G. Turro, J. Phys. Chem. 1983, 87, 531–532.
65. M. Majek, A. Jacobi von Wangelin, Angew. Chem. Int. Ed. 2015, 54, 2270–2274;
66. Angew. Chem. 2015, 127, 2298–2302.
67. P. Gautam, B. M. Bhanage, Catal. Sci. Technol. 2015, 5, 4663–4702.
68. V. V. Grushin, H. Alper, Organometallics 1993, 12, 3846–3850.
69. S. Korsager, R. Taaning, A. Lindhardt, T. Skrydstrup, J. Org. Chem. 2013, 78, 6112–6120.
70. T. Ueda, H. Konishi, K. Manabe, Org. Lett. 2012, 14, 3100–3103.
71. S. Gockel, K. Hull, Org. Lett. 2015, 17, 3236–3239.
72. S. V. F. Hansen, T. Ulven, Org. Lett. 2015, 17, 2832–2835.
73. R. Ballardini, G. Varani, M. T. Indelli, F. Scandola, V. Balzani, J. Am. Chem. Soc. 1978, 100, 7219–7223.
74. J. Zhang, M.-Z. Jin, W. Zhang, L. Yang, Z.-L. Liu, Tetrahedron Lett. 2002, 43, 9687–9689.
75. R. I. J. Amos, B. S. Gourlay, B. F. Yates, C. H. Schiesser, T. W. Lewis, J. A. Smith, Org. Biomol. Chem. 2013, 11, 170–176.
76. M. G. Voronkov, I. P. Tsyrendorzhieva, V. I. Rakhlin, Russ. J. Org. Chem. 2008, 44, 481–484.
77. N. Menshutkin, Z. Physik. Chem. 1890, 5, 589.
78. Y. Li, F. Jia, Z. Li, Chem. Eur. J. 2013, 19, 82–86.
79. T. Fang, X. Gao, R. Tang, X. Zhang, C. Deng, Chem. Commun. 2014, 50, 14775–14777.
80. R. S. Mane, B. M. Bhanage, J. Org. Chem. 2016, 81, 1223–1228.
81. T. Hu, N. Wang, T. Nguyen, N. Zheng, Beilstein J. Org. Chem. 2013, 9, 1977–2001.
82. J. M. Narayanam, J. W. Tucker, J. R. C. Stephenson, J. Am. Chem. Soc. 2009, 131, 8756–8757.