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-00000083.xml
Synlett 2013; 24(12): 1578-1582
DOI: 10.1055/s-0033-1339182
DOI: 10.1055/s-0033-1339182
letter
Photocatalytic Cascade Carbon–Carbon Bond-Forming Radical Reaction in Aqueous Media
Weitere Informationen
Publikationsverlauf
Received: 08. Mai 2013
Accepted after revision: 13. Mai 2013
Publikationsdatum:
14. Juni 2013 (online)
![](https://www.thieme-connect.de/media/synlett/201312/lookinside/thumbnails/10.1055-s-0033-1339182-1.jpg)
Abstract
The ruthenium photocatalyst Ru(bpy)3Cl2·6H2O has the potential to catalyze the cascade radical reaction with perfluoroalkyl radicals in aqueous media via two photoredox cycles.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References and Notes
- 1 Anastas PT, Warner JC In Green Chemistry Theory and Practice . Oxford University Press; New York: 1998
- 2 Li C.-J, Chan T.-H In Comprehensive Organic Reactions in Aqueous Media . John Wiley and Sons; Hoboken: 2007
- 4 Perchyonok VT In Radical Reactions in Aqueous Media . RSC Green Chemistry No. 6, RSC Publishing; Cambridge: 2010
- 5 Yorimitsu H, Shinokubo H, Oshima K. Synlett 2002; 674
- 6a Ueda M, Miyabe H, Nishimura A, Miyata O, Takemoto Y, Naito T. Org. Lett. 2003; 5: 3835
- 6b Huang T, Keh CC. K, Li CJ. Chem. Commun. 2002; 2440
- 7a Shi L, Xia W. Chem. Soc. Rev. 2012; 41: 7687
- 7b Ischay MA, Yoon TP. Eur. J. Org. Chem. 2012; 3359
- 7c Tucker JW, Stephenson CR. J. J. Org. Chem. 2012; 77: 1617
-
7d Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102
- 8a Nicewicz DA, MacMillan DW. C. Science 2008; 322: 77
- 8b Ischay MA, Anzovino ME, Du J, Yoon TP. J. Am. Chem. Soc. 2008; 130: 12886
- 8c Narayanam JM. R, Tucker JW, Stephenson CR. J. J. Am. Chem. Soc. 2009; 131: 8756
- 8d Larraufie M.-H, Pellet R, Fensterbank L, Goddard J.-P, Lacôte E, Malacria M, Ollivier C. Angew. Chem. Int. Ed. 2011; 50: 4463
- 8e Lin S, Ischay MA, Fry CG, Yoon TP. J. Am. Chem. Soc. 2011; 133: 19350
- 8f McNally A, Prier CK, MacMillan DW. C. Science 2011; 334: 1114
- 8g Maity S, Zhu M, Shinabery RS, Zheng N. Angew. Chem. Int. Ed. 2012; 51: 6119
- 8h Miyake Y, Nakajima K, Nishibayashi Y. J. Am. Chem. Soc. 2012; 134: 19350
-
9a Tucker JW, Nguyen JD, Narayanam JM. R, Krabbe SW, Stephenson CR. J. Chem. Commun. 2010; 46: 4985
- 9b Shih H.-W, Wal MN. V, Grange RL, MacMillan DW. C. J. Am. Chem. Soc. 2010; 132: 13600
- 9c Nguyen JD, D’Amato EM, Narayanam JM. R, Stephenson CR. J. Nat. Chem. 2012; 4: 854
- 9d Andrews RS, Becker JJ, Gagné MR. Angew. Chem. Int. Ed. 2012; 51: 4140
- 9e Freeman DB, Furst L, Condie AG, Stephenson CR. J. Org. Lett. 2012; 14: 94
- 10a Nagib DA, Scott ME, MacMillan DW. C. J. Am. Chem. Soc. 2009; 131: 10875
- 10b Pham PV, Nagib DA, MacMillan DW. C. Angew. Chem. Int. Ed. 2011; 50: 6119
- 10c Nagib DA, MacMillan DW. C. Nature (London) 2011; 480: 224
- 11a Nguyen JD, Tucker JW, Konieczynska MD, Stephenson CR. J. J. Am. Chem. Soc. 2011; 133: 4160
-
11b Rueping M, Zhu S, Koenigs RM. Chem. Commun. 2011; 47: 8679
- 11c Tucker JW, Zhang Y, Jamison TF, Stephenson CR. J. Angew. Chem. Int. Ed. 2012; 51: 4144
- 11d Zen JM, Liou SL, Kumar AS, Hsia MS. Angew. Chem. Int. Ed. 2003; 42: 577
- 12a Balzani V, Bolletta F, Gandolfi MT, Maestri M. Top. Curr. Chem. 1978; 75: 1
- 12b Campagna S, Puntoriero F, Nastasi F, Bergamini G, Balzani V. Top. Curr. Chem. 2007; 280: 117
- 12c Bock CR, Meyer TJ, Whitten DG. J. Am. Chem. Soc. 1975; 97: 2909
- 12d Bock CR, Connor JA, Gutierrez AR, Meyer TJ, Whitten DG, Sullivan BP, Nagle JK. J. Am. Chem. Soc. 1979; 101: 4815
- 12e Lin C.-T, Böttcher W, Chou M, Creutz C, Sutin N. J. Am. Chem. Soc. 1976; 98: 6536
- 13 Yoshioka E, Kohtani S, Sawai K, Kentefu Tanaka E, Miyabe H. J. Org. Chem. 2012; 77: 8588
- 14a Hu C.-M, Qiu Y.-L. Tetrahedron Lett. 1991; 32: 4001
- 14b Hu C.-M, Qiu Y.-L. J. Org. Chem. 1992; 57: 3339
- 14c Hu C.-M, Chen J. J. Chem. Soc., Chem. Commun. 1993; 72
- 14d Chen J, Hu C.-M. J. Chem. Soc., Perkin Trans. 1 1994; 1111
- 14e Ding Y, Zhao G, Huang WY. Tetrahedron Lett. 1992; 33: 8119
- 14f Qiu Z.-M, Burton DJ. J. Org. Chem. 1995; 60: 3465
- 14g Yajima T, Nagano H, Saito C. Tetrahedron Lett. 2003; 44: 7027
- 14h Yajima T, Nagano H. Org. Lett. 2007; 9: 2513
- 14i Tonoi T, Nishikawa A, Yajima T, Nagano H, Mikami K. Eur. J. Org. Chem. 2008; 1331
- 14j Ueda M, Iwasada E, Miyabe H, Miyata O, Naito T. Synthesis 2010; 1999
- 15 Montalti M, Credi A, Prodi L, Gandolfi MT In Handbook of Photochemistry . 3rd ed. CRC Press; Boca Raton: 2006
- 16 Pischel U, Zhang X, Hellrung B, Haselbach E, Muller P.-A, Nau WM. J. Am. Chem. Soc. 2000; 122: 2027
- 17a Rozhkov IN, Igumnov SM, Bekker GY, Pletnev SI, Rempel GD, Deev LE. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1990; 38: 2041
- 17b Rozhkov IN, Igumnov SM, Bekker GY, Pletnev SI, Rempel GD, Deev LE. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya 1989; 10: 2222
- 18 Dolbier WR. Jr. Chem. Rev. 1996; 96: 1557
- 19 Reaction of 1 with CCl3Br (5 equiv) and Et3B (1.0 M in hexane, 5 equiv) in CH2Cl2 gave the products in 17% combined yield.
- 20 Fu Y, Liu L, Yu H.-Z, Wang Y.-M, Guo Q.-X. J. Am. Chem. Soc. 2005; 127: 7227 ; adjusted by subtracting 0.24 V from the original value of +0.17 V vs. standard hydrogen electrode
For some reviews, see:
For photocatalysis of halogen compounds, see:
For the photocatalysis using perfluoroalkyl iodides, see:
For the photocatalysis in aqueous media, see:
For the reaction with perfluoroalkyl radicals, see: