New safety-catch photolabile protecting group

Organic Letters

Volumn 9, Issue 26, 2007, Pages 5453-5456

  Riguet, Emmanuel ^a   Bochet, Christian G ^a  

^a UNIVERSITY OF FRIBOURG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 38349176363     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702327c     Document Type: Article

References (17)

1. (a) Falvey, D. E.; Sundararajan, C. Pholochem. Photobiol. Sci. 2004, 3, 831.
2. (b) Pelliccioli, A. P.; Wirz, J. Photochem. Photobiol. Sci. 2002, 1, 441.
3. (c) Bochet, C. G. J. Chem. Soc., Perkin Trans. 1 2002, 125.
4. (d) Pillai, V. N. R. Org. Photochem. 1987, 9, 225.
5. (a) Blanc, A.; Bochet, C. G. Org. Lett. 2007, 9, 2649.
6. (b) Blanc, A.; Bochet, C. G. J. Org. Chem. 2002, 67, 5567.
7. (c) Bochet, C. G. Angew. Chem. Int. Ed. 2001, 40, 2071.
8. Kenner, G. W.; McDermott, J. R.; Sheppard, R. C. Chem. Commun. 1971, 636.
9. For a more recent overview, see: Seneci, P. Solid-Phase Synthesis and Combinatorial Technologies; John Wiley: New York, 2000; p 17.
10. Bochet, C. G. Tetrahedron Lett. 2000, 41, 6341 and references therein.
11. Patchornik, A.; Amit, B.; Woodward, R. B. J. Am. Chem. Soc. 1970, 92, 6333.
12. Charier, S.; Ruel, O.; Baudin, J. B.; Alcor, D.; Allemand, J. F.; Meglio, A.; Jullien, L.; Valeur, B. Chem. - Eur. J. 2006, 12, 1097-1113.
13. (a) Hellrung, B.; Kamdzhilov, Y.; Schwörer, M.; Wirz, J. J. Am. Chem. Soc. 2005, 127, 8934.
14. (b) Corrie, J. E. T.; Barth, A.; Munasinghe, V. R. N.; Trentham, D. R.; Hutter, M. C. J. Am. Chem. Soc 2003, 125, 8546.
15. Aniline radical cations can be generated by Cu(II) under specific circumstances, as shown recently. See: Kirchgessner, M.; Sreenath, K.; Gopidas, K. R. J. Org. Chem. 2006, 71, 9849.
16. Efficient, safety-catch photolabile linkers have been described recently, triggered by the hydrolysis of thioketals or ketals: (a) Cano, M.; Ladlow, M.; Balasubramanian, S. J. Org. Chem. 2002, 67, 129-135.
17. (b) Flickinger, S. T.; Patel, M.; Binkowski, B. F.; Lowe, A. M.; Li, M. H.; Kim, C.; Cerrina, F.; Belshaw, P. J. Org. Lett. 2006, 8, 2357-2360.