Visible-Light-Accelerated C−H Sulfinylation of Heteroarenes

Angewandte Chemie - International Edition

Volumn 56, Issue 1, 2017, Pages 409-412

  Meyer, Andreas Uwe ^a   Wimmer, Alexander ^a   König, Burkhard ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Friedel Crafts reaction; metal free conditions; sulfinylation; sulfoxide; visible light

Indexed keywords

CHEMICAL ENGINEERING; CHEMICAL REACTIONS; CHEMISTRY;

ELECTROPHILIC AROMATIC SUBSTITUTIONS; METAL-FREE CONDITIONS; NATURAL PRODUCTS; PEROXODISULFATE; STRUCTURAL MOTIFS; SULFINYLATION; SULFOXIDE; VISIBLE LIGHT;

LIGHT;

EID: 85006307106     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201610210     Document Type: Article

References (68)

1. K. Suwanborirux, K. Charupant, S. Amnuoypol, S. Pummangura, A. Kubo, N. Saito, J. Nat. Prod. 2002, 65, 935–937;
2. S. Kim, R. Kubec, R. A. Musah, J. Ethnopharmacol. 2006, 104, 188–192;
3. I. Dini, G. C. Tenore, A. Dini, J. Nat. Prod. 2008, 71, 2036–2037;
4. M. El-Aasr, Y. Fujiwara, M. Takeya, T. Ikeda, S. Tsukamoto, M. Ono, D. Nakano, M. Okawa, J. Kinjo, H. Yoshimitsu, T. Nohara, J. Nat. Prod. 2010, 73, 1306–1308;
5. T. P. Wyche, J. S. Piotrowski, Y. Hou, D. Braun, R. Deshpande, S. McIlwain, I. M. Ong, C. L. Myers, I. A. Guzei, W. M. Westler, D. R. Andes, T. S. Bugni, Angew. Chem. Int. Ed. 2014, 53, 11583–11586;
6. Angew. Chem. 2014, 126, 11767–11770.
7. J. Legros, J. R. Dehli, C. Bolm, Adv. Synth. Catal. 2005, 347, 19–31;
8. R. Bentley, Chem. Soc. Rev. 2005, 34, 609.
9. T. Buronfosse, P. Moroni, E. Benoît, J. L. Rivière, J. Biochem. Toxicol. 1995, 10, 179–189.
10. T. Oyama, K. Naka, Y. Chujo, Macromolecules 1999, 32, 5240–5242;
11. M. Numata, Y. Aoyagi, Y. Tsuda, T. Yarita, A. Takatsu, Anal. Chem. 2007, 79, 9211–9217.
12. F. Weber, G. Sedelmeier, Nachr. Chem. 2013, 61, 528–529.
13. F. Weber, G. Sedelmeier, Nachr. Chem. 2014, 62, 997–997.
14. I. Fernández, N. Khiar, Chem. Rev. 2003, 103, 3651–3706.
15. M. Mellah, A. Voituriez, E. Schulz, Chem. Rev. 2007, 107, 5133–5209;
16. R. Mariz, X. Luan, M. Gatti, A. Linden, R. Dorta, J. Am. Chem. Soc. 2008, 130, 2172–2173;
17. J. Chen, J. Chen, F. Lang, X. Zhang, L. Cun, J. Zhu, J. Deng, J. Liao, J. Am. Chem. Soc. 2010, 132, 4552–4553;
18. E. M. Stang, M. C. White, J. Am. Chem. Soc. 2011, 133, 14892–14895;
19. C. Jiang, D. J. Covell, A. F. Stepan, M. S. Plummer, M. C. White, Org. Lett. 2012, 14, 1386–1389;
20. B. M. Trost, M. C. Ryan, M. Rao, T. Z. Markovic, J. Am. Chem. Soc. 2014, 136, 17422–17425;
21. G. Sipos, E. E. Drinkel, R. Dorta, Chem. Soc. Rev. 2015, 44, 3834–3860;
22. B. M. Trost, M. Rao, Angew. Chem. Int. Ed. 2015, 54, 5026–5043;
23. Angew. Chem. 2015, 127, 5112–5130.
24. C. Bolm, Coord. Chem. Rev. 2003, 237, 245–256;
25. E. Wojaczyńska, J. Wojaczyński, Chem. Rev. 2010, 110, 4303–4356;
26. P. K. Dornan, P. L. Leung, V. M. Dong, Tetrahedron 2011, 67, 4378–4384;
27. T. Neveselý, E. Svobodová, J. Chudoba, M. Sikorski, R. Cibulka, Adv. Synth. Catal. 2016, 358, 1654–1663.
28. K. Hiroi, F. Kato, Tetrahedron 2001, 57, 1543–1550;
29. Z. Han, D. Krishnamurthy, P. Grover, Q. K. Fang, X. Su, H. S. Wilkinson, Z.-H. Lu, D. Magiera, C. H. Senanayake, Tetrahedron 2005, 61, 6386–6408;
30. F. Xue, D. Wang, X. Li, B. Wan, J. Org. Chem. 2012, 77, 3071–3081.
31. F. Sandrinelli, S. Perrio, M.-T. Averbuch-Pouchot, Org. Lett. 2002, 4, 3619–3622;
32. C. Caupène, C. Boudou, S. Perrio, P. Metzner, J. Org. Chem. 2005, 70, 2812–2815;
33. G. Maitro, G. Prestat, D. Madec, G. Poli, J. Org. Chem. 2006, 71, 7449–7454;
34. G. Maitro, G. Prestat, D. Madec, G. Poli, Tetrahedron: Asymmetry 2010, 21, 1075–1084;
35. M. Zhang, T. Jia, H. Yin, P. J. Carroll, E. J. Schelter, P. J. Walsh, Angew. Chem. Int. Ed. 2014, 53, 10755–10758;
36. Angew. Chem. 2014, 126, 10931–10934;
37. L. Zong, X. Ban, C. W. Kee, C.-H. Tan, Angew. Chem. Int. Ed. 2014, 53, 11849–11853;
38. Angew. Chem. 2014, 126, 12043–12047;
39. A. L. Schwan, ChemCatChem 2015, 7, 226–227;
40. M. Zhang, T. Jia, I. K. Sagamanova, M. A. Pericás, P. J. Walsh, Org. Lett. 2015, 17, 1164–1167.
41. G. Maitro, S. Vogel, G. Prestat, D. Madec, G. Poli, Org. Lett. 2006, 8, 5951–5954;
42. G. Maitro, S. Vogel, M. Sadaoui, G. Prestat, D. Madec, G. Poli, Org. Lett. 2007, 9, 5493–5496;
43. E. Bernoud, G. Le Duc, X. Bantreil, G. Prestat, D. Madec, G. Poli, Org. Lett. 2010, 12, 320–323.
44. T. Jia, A. Bellomo, K. E. L. Baina, S. D. Dreher, P. J. Walsh, J. Am. Chem. Soc. 2013, 135, 3740–3743;
45. T. Jia, A. Bellomo, S. Montel, M. Zhang, K. El Baina, B. Zheng, P. J. Walsh, Angew. Chem. Int. Ed. 2014, 53, 260–264;
46. Angew. Chem. 2014, 126, 264–268;
47. T. Jia, M. Zhang, H. Jiang, C. Y. Wang, P. J. Walsh, J. Am. Chem. Soc. 2015, 137, 13887–13893;
48. T. Jia, M. Zhang, I. K. Sagamanova, C. Y. Wang, P. J. Walsh, Org. Lett. 2015, 17, 1168–1171;
49. H. Jiang, T. Jia, M. Zhang, P. J. Walsh, Org. Lett. 2016, 18, 972–975.
50. F. Izquierdo, A. Chartoire, S. P. Nolan, ACS Catal. 2013, 3, 2190–2193.
51. F. Gelat, J.-F. Lohier, A.-C. Gaumont, S. Perrio, Adv. Synth. Catal. 2015, 357, 2011–2016.
52. G. A. Olah, J. Nishimura, J. Org. Chem. 1974, 39, 1203–1205.
53. F. Yuste, A. I. Hernández Linares, V. M. Mastranzo, B. Ortiz, R. Sánchez-Obregón, A. Fraile, J. L. García Ruano, J. Org. Chem. 2011, 76, 4635–4644.
54. T. Miao, P. Li, Y. Zhang, L. Wang, Org. Lett. 2015, 17, 832–835.
55. C. Dai, F. Meschini, J. M. R. Narayanam, C. R. J. Stephenson, J. Org. Chem. 2012, 77, 4425–4431.
56. Y. Fujiwara, J. A. Dixon, F. O'Hara, E. D. Funder, D. D. Dixon, R. A. Rodriguez, R. D. Baxter, B. Herlé, N. Sach, M. R. Collins, Y. Ishihara, P. S. Baran, Nature 2012, 492, 95–99.
57. The low yield of 3 ac results from the low nucleophilicity of 2 o and the formation of byproduct 3 ac′ (see the Supporting Information).
58. M. Kędziorek, P. Mayer, H. Mayr, Eur. J. Org. Chem. 2009, 1202–1206.
59. F. Minisci, A. Citterio, C. Giordano, Acc. Chem. Res. 1983, 16, 27–32;
60. R. E. Huie, C. L. Clifton, P. Neta, Int. J. Radiat. Appl. Instrum. 1991, 38, 477–481;
61. Y. Wu, A. Bianco, M. Brigante, W. Dong, P. de Sainte-Claire, K. Hanna, G. Mailhot, Environ. Sci. Technol. 2015, 49, 14343–14349.
62. F. M'Halla, J. Pinson, J. M. Saveant, J. Am. Chem. Soc. 1980, 102, 4120–4127.
63. S. Lakhdar, M. Westermaier, F. Terrier, R. Goumont, T. Boubaker, A. R. Ofial, H. Mayr, J. Org. Chem. 2006, 71, 9088–9095;
64. T. A. Nigst, M. Westermaier, A. R. Ofial, H. Mayr, Eur. J. Org. Chem. 2008, 2369–2374.
65. E. A. Hill, M. L. Gross, M. Stasiewicz, M. Manion, J. Am. Chem. Soc. 1969, 91, 7381–7392;
66. H. Mayr, B. Kempf, A. R. Ofial, Acc. Chem. Res. 2003, 36, 66–77.
67. A. U. Meyer, A. L. Berger, B. König, Chem. Commun. 2016, 52, 10918–10921.
68. N. A. Romero, K. A. Margrey, N. E. Tay, D. A. Nicewicz, Science 2015, 349, 1326–1330.