N-iodosuccinimide-promoted hofmann-löffler reactions of sulfonimides under visible light

Organic Letters

Volumn 18, Issue 3, 2016, Pages 436-439

  O'Broin, Calvin Q ^a   Fernández, Patricia ^a   Martínez, Claudio ^a   Muñiz, Kilian ^a,b  

^a BARCELONA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Spain)

^b INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

IODINE; N-IODOSUCCINIMIDE; NITROGEN; PYRROLIDINE DERIVATIVE; SUCCINIMIDE DERIVATIVE; SULFONAMIDE;

AMINATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; LIGHT; SYNTHESIS;

AMINATION; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; IODINE; LIGHT; MOLECULAR STRUCTURE; NITROGEN; PYRROLIDINES; SUCCINIMIDES; SULFONAMIDES;

EID: 84957876121     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b03476     Document Type: Article

References (40)

1. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147 10.1021/cr900184e
2. MunÌ?iz, K. Angew. Chem., Int. Ed. 2009, 48, 9412 10.1002/anie.200903671
3. Davies, H. M. L. R.; Long, M. S. Angew. Chem., Int. Ed. 2005, 44, 3518 10.1002/anie.200500554
4. Ramirez, T. A.; Zhao, B.; Shi, Y. Chem. Soc. Rev. 2012, 41, 931 10.1039/C1CS15104E
5. Roizen, J. L.; Harvey, M. E.; Du Bois, J. Acc. Chem. Res. 2012, 45, 911 10.1021/ar200318q
6. Collet, F.; Lescot, C.; Dauban, P. Chem. Soc. Rev. 2011, 40, 1926 10.1039/c0cs00095g
7. Dauban, P.; Dodd, R. H. Synlett 2003, 1571 10.1055/s-2003-41010
8. Díaz-Requejo, M. M.; Caballero, A.; Fructos, M. R.; Pérez, P. J. In Alkane C-H Activation by Single-Site Metal Catalysis. In Catalysis by Metal Complexes; Pérez, P. J., Ed.; Springer: Berlin, 2012; Vol. 38, Chapter 6, pp 229-264.
9. Reetz, M. T. J. Am. Chem. Soc. 2013, 135, 12480 10.1021/ja405051f
10. Renata, H.; Wang, Z. J.; Arnold, F. H. Angew. Chem., Int. Ed. 2015, 54, 3351 10.1002/anie.201409470
11. McIntosh, J. A.; Coelho, P. S.; Farwell, C. C.; Wang, Z. J.; Lewis, J. C.; Brown, T. R.; Arnold, F. H. Angew. Chem., Int. Ed. 2013, 52, 9309 10.1002/anie.201304401
12. Hyster, T. K.; Farwell, C. C.; Buller, A. R.; McIntosh, J. A.; Arnold, F. H. J. Am. Chem. Soc. 2014, 136, 15505 10.1021/ja509308v
13. Berkessel, A.; Groeger, H. Asymmetric Organocatalysis. Wiley-VCH: Weinheim 2005.
14. List, B. Special issue Organocatalysis Chem. Rev. 2007, 107, 5413 10.1021/cr078412e
15. MacMillan, D. C. Nature 2008, 455, 304 10.1038/nature07367
16. For exceptionally general oxidation reactions, see: Zhu, Y.; Wang, Q.; Cornwall, R. G.; Shi, Y. Chem. Rev. 2014, 114, 8199 10.1021/cr500064w
17. Wolff, M. E. Chem. Rev. 1963, 63, 55 10.1021/cr60221a004
18. Neale, R. S. Synthesis 1971, 1971, 1 10.1055/s-1971-21662
19. Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337 10.1002/anie.198303373
20. Jeffrey, J. L.; Sarpong, R. Chem. Sci. 2013, 4, 4092 10.1039/c3sc51420j
21. Hernández, R.; Rivera, A.; Salazar, J. A.; Suárez, E. J. Chem. Soc., Chem. Commun. 1980, 20, 958 10.1039/c39800000958
22. Betancor, C.; Concepción, J. I.; Hernández, R.; Salazar, J. A.; Suárez, E. J. Org. Chem. 1983, 48, 4430 10.1021/jo00171a066
23. De Armas, P.; Carrau, R.; Concepción, J. I.; Francisco, C. G.; Hernández, R.; Suárez, E. Tetrahedron Lett. 1985, 26, 2493 10.1016/S0040-4039(00)94862-7
24. Carrau, R.; Hernández, R.; Suárez, E.; Betancor, C. J. Chem. Soc., Perkin Trans. 1 1987, 937 10.1039/p19870000937
25. De Armas, P.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E. J. Chem. Soc., Perkin Trans. 1 1988, 3255 10.1039/p19880003255
26. Zhdankin, V. V. Hypervalent Iodine Chemistry Preparation, Structure and Synthetic Applications of Polyvalent Iodine Compounds; John Wiley & Sons: West Sussex, 2014.
27. Hypervalent Iodine Chemistry. Modern Developments in Organic Synthesis. In Topics in Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
28. Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123 10.1021/cr940424+
29. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523 10.1021/cr010003+
30. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299 10.1021/cr800332c
31. Fan, R.; Pu, D.; Wen, F.; Wu, J. J. Org. Chem. 2007, 72, 8994 10.1021/jo7016982
32. Martínez, C.; MunÌ?iz, K. Angew. Chem., Int. Ed. 2015, 54, 8287 10.1002/anie.201501122
33. In addition, recent progress has identified hypervalent iodine catalysis for C-H amination: Zhu, C.; Liang, Y.; Hong, X.; Sun, H.; Sun, W.-Y.; Houk, K. N.; Shi, Z. J. Am. Chem. Soc. 2015, 137, 7564 10.1021/jacs.5b03488
34. Qin, Q.; Yu, S. Org. Lett. 2015, 17, 1894 10.1021/acs.orglett.5b00582
35. Chavez, P.; Kirsch, J.; Hövelmann, C. H.; Streuff, J.; M. Martínez-Belmonte, M.; Escudero-Adán, E. C.; Martin, E.; MunÌ?iz, K. Chem. Sci. 2012, 3, 2375 10.1039/c2sc20242e
36. Paz, N. R.; Rodríguez-Sosa, D.; Valdés, H.; Marticorena, R.; Melián, D.; Copano, M. B.; González, C. C.; Herrera, A. J. Org. Lett. 2015, 17, 2370 10.1021/acs.orglett.5b00866
37. Souto, J. A.; Zian, D.; MunÌ?iz, K. J. Am. Chem. Soc. 2012, 134, 7242 10.1021/ja3013193
38. Sun, J.; Wang, Y.; Pan, Y. J. Org. Chem. 2015, 80, 8945 10.1021/acs.joc.5b01383
39. Wei, Y.; Liang, F. S.; Zhang, X. T. Org. Lett. 2013, 15, 5186 10.1021/ol402287n
40. Zhang, X.; Wang, M.; Li, P.; Wang, L. Chem. Commun. 2014, 50, 8006 10.1039/c4cc01189a