A clean and selective radical homocoupling employing carboxylic acids with titania photoredox catalysis

Organic Letters

Volumn 16, Issue 20, 2014, Pages 5394-5397

  Manley, David W ^a   Walton, John C ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84908062867     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502625w     Document Type: Article

References (30)

1. Voloshchuk, T.; Farina, N. S.; Wauchope, O. R.; Kiprowska, M.; Haberfield, P.; Greer, A. J. Nat. Prod. 2004, 67, 1141-1146.
2. Vrettou, M.; Gray, A. A.; Brewer, A. R. E.; Barrett, A. G. M. Tetrahedron 2007, 63, 1487-1536.
3. Lian, G.; Yu, B. Chem. Biodiversity 2010, 7, 2660-2691.
4. Venkatraman, S.; Li, C.-J. Org. Lett. 1999, 1, 1133-1135.
5. Lin, G.-q.; Hong, R. J. Org. Chem. 2001, 66, 2877-2880.
6. Lee, P. H.; Seomoon, D.; Lee, K. Org. Lett. 2004, 7, 343-345.
7. Curran, D. P. Synthesis 1988, 1988, 417-439.
8. Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237-1286.
9. Baguley, P. A.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 1998, 2073-2082.
10. Studer, A.; Amrein, S. Synthesis 2002, 14, 835-849.
11. Kürti, L.; Czakó, B. Strategic Applications of Named Reactions in Organic Synthesis: Background and Detailed Mechanisms; Elsevier Academic Press: 2005.
12. United States Environmental Protection Agrency, Green Chemistry Page. http://www2.epa.gov/green-chemistry (accessed Aug 13, 2014).
13. Manley, D. W.; McBurney, R. T.; Miller, P.; Howe, R. F.; Rhydderch, S.; Walton, J. C. J. Am. Chem. Soc. 2012, 134, 13580-13583.
14. Manley, D. W.; McBurney, R. T.; Miller, P.; Walton, J. C.; Mills, A.; O'Rourke, C. J. Org. Chem. 2014, 79, 1386-1398.
15. Mills, A.; O'Rourke, C. Catal. Today 2014, 230, 256-264.
16. Compound 10 might have formed either by hole-oxidation of the trityl radical to a cation which then underwent electrophilic aromatic substitution with a neighbouring phenyl ring or via homolytic aromatic substitution followed by oxidative rearomatization.
17. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry; Oxford University Press: Oxford, 2012; Vol. 1.
18. 19F NMR spectra revealed that, as expected, the D/L and meso isomers were present in a 1:1 ratio.
19. Uneyama, K. Organofluorine Chemistry; Wiley: 2006.
20. Studer, A. Chem. - Eur. J. 2001, 7, 1159-1164.
21. Fischer, H. Chem. Rev. 2001, 101, 3581-3610.
22. Studer, A. Chem. Soc. Rev. 2004, 33, 267-273.
23. Yeung, K.-S.; Paterson, I. Angew. Chem., Int. Ed. 2002, 41, 4632-4653.
24. Blankenstein, J.; Zhu, J. Eur. J. Org. Chem. 2005, 2005, 1949-1964.
25. Linsebigler, A. L.; Lu, G.; Yates, J. T. Chem. Rev. 1995, 95, 735-758.
26. Deiana, C.; Fois, E.; Coluccia, S.; Martra, G. J. Phys. Chem. C 2010, 114, 21531-21538.
27. Salazar, C.; Nanny, M. A. J. Catal. 2010, 269, 404-410.
28. Henderson, M. A. Surf. Sci. Rep. 2011, 66, 185-297.
29. Marinkovic, S.; Hoffmann, N. Chem. Commun. 2001, 1576-1578.
30. Marinković, S.; Hoffmann, N. Eur. J. Org. Chem. 2004, 3102-3107.