RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2013; 45(19): 2699-2705
DOI: 10.1055/s-0033-1338419
DOI: 10.1055/s-0033-1338419
special topic
Reductive Cyclizations of Nitroarenes to Hydroxamic Acids by Visible Light Photoredox Catalysis
Weitere Informationen
Publikationsverlauf
Received: 01. März 2013
Accepted: 17. März 2013
Publikationsdatum:
24. April 2013 (online)
Abstract
We have developed a photocatalytic reduction of nitroarenes as an efficient, chemoselective route to biologically important N-phenyl hydroxamic acid scaffolds. Optimal conditions call for 2.5 mol% of a ruthenium photocatalyst, visible light irradiation, and a dihydropyridine terminal reductant. Because of the mild nature of the visible light activation, functional groups that might be sensitive to other non-photochemical reduction methods are easily tolerated.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 Kurzak B, Kozłowski H, Farkas E. Coord. Chem. Rev. 1992; 114: 169
- 2a Weisburger JH, Weisburger EK. Pharmacol. Rev. 1973; 25: 1
- 2b Hider RC, Kong X. Nat. Prod. Rep. 2010; 27: 637
- 3a Miller MJ. Chem. Rev. 1989; 89: 1563
- 3b Muri EM. F, Nieto MJ, Sindelar RD, Williamson JS. Curr. Med. Chem. 2002; 9: 1631
- 4a Wright WB, Collins KH. J. Am. Chem. Soc. 1956; 78: 221
- 4b Sicker D, Prätorius B, Mann G, Meyer L. Synthesis 1989; 211
- 4c McAllister LA, Bechle BM, Dounay AB, Evrard E, Gan X, Ghosh S, Kim J.-Y, Parikh VD, Tuttle JB, Verhoest PR. J. Org. Chem. 2011; 76: 3484
- 5 Coutts RT, Wibberley DG. J. Chem. Soc. 1963; 4610
- 6 Davis AL, Choun OH. P, Cook DE, McCord TJ. J. Med. Chem. 1964; 7: 632
- 7a Zeitler K. Angew. Chem. Int. Ed. 2009; 48: 9785
-
7b Yoon TP, Ischay MA, Du J. Nat. Chem. 2010; 2: 527
-
7c Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102
- 7d Telpý F. Collect. Czech. Chem. Commun. 2011; 76: 859
- 7e Tucker JW, Stephenson CR. J. J. Org. Chem. 2012; 77: 1617
- 7f Xuan J, Xiao W.-J. Angew. Chem. Int. Ed. 2012; 51: 6828
- 8a Ischay MA, Anzovino ME, Du J, Yoon TP. J. Am. Chem. Soc. 2008; 130: 12886
- 8b Du J, Yoon TP. J. Am. Chem. Soc. 2009; 131: 14604
-
8c Ischay MA, Lu Z, Yoon TP. J. Am. Chem. Soc. 2010; 132: 8572
- 8d Du J, Ruiz Espelt L, Guzei IA, Yoon TP. Chem. Sci. 2011; 2: 2115
- 8e Ischay MA, Ament MS, Yoon TP. Chem. Sci. 2012; 3: 2807
- 9a Nicewicz DA, MacMillan DW. C. Science (Washington, D.C.) 2008; 322: 77
- 9b Narayanam JM. R, Tucker JW, Stephenson CR. J. J. Am. Chem. Soc. 2009; 131: 8756
- 9c McNally A, Prier CK, MacMillan DW. C. Science (Washington, D.C.) 2011; 334: 1114
- 9d Kalyani D, McMurtrey KB, Neufeldt SR, Sanford MS. J. Am. Chem. Soc. 2011; 133: 18566
- 9e Freeman DB, Furst L, Condie AG, Stephenson CR. J. Org. Lett. 2012; 14: 94
- 9f Maity S, Zhu M, Shinabery RS, Zheng N. Angew. Chem. Int. Ed. 2012; 51: 222
- 9g Leung JC. T, Chatalova-Sazepin C, West JG, Rueda-Becerril M, Paquin JF, Sammis GM. Angew. Chem. Int. Ed. 2012; 51: 10804
- 10 Hirao T, Shiori J, Okahata N. Bull. Chem. Soc. Jpn. 2004; 77: 1763
- 11 Tomioka H, Ueda K, Ohi H, Izawa Y. Chem. Lett. 1986; 1359
- 12a Davis AL, Choun OH. P, Cook DE, McCord TJ. J. Med. Chem. 1964; 7: 632
- 12b Davis AL, Chambers WH, Kelley DH, Fell DA, Haynes JR, Hulme KL, Gage LD, McCord TJ. J. Med. Chem. 1975; 18: 752
- 12c Erhardt S, Olsson SK, Engberg G. CNS Drugs 2009; 23: 91
- 13a Dong W, Jimenez LS. J. Org. Chem. 1999; 64: 2520
- 13b Wong A, Kuethe JT, Davies IW. J. Org. Chem. 2003; 68: 9865
- 13c Wong A, Kuethe JT, Davies IW, Hughes DL. J. Org. Chem. 2004; 69: 7761
- 13d Nicolaou KC, Lee SH, Estrada AA, Zak M. Angew. Chem. Int. Ed. 2005; 44: 3736
- 14 Claffey MM, Dounay AB, Gan X, Hayward MM, Rong S, Tuttle JB, Verhoest PR. WO 2010146488, 2010
- 15 Wang G.-W, Xia J.-J, Miao C.-B, Wu X.-L. Bull. Chem. Soc. Jpn. 2006; 79: 454
- 16 Zhou W, Zhang L, Jiao N. Tetrahedron 2009; 65: 1982
- 17 Murahashi S.-I, Oda T, Sugahara T, Masui Y. J. Org. Chem. 1990; 55: 1744
- 18 Liu B, Hu L. Bioorg. Med. Chem. 2003; 11: 3889
For reviews, see:
For leading examples from other groups, see: