The photon is the green reagent par excellence. It is absorbed leaving no residue and induces deep-seated chemical transformations under mild conditions. Reactions via electronic excited states often reach the target via a shorter path than thermal alternatives, with excellent atom economy. Photochemistry also offers a way for the mild generation of highly reactive intermediates such as radicals or ions. This is illustrated by the example of arylation reactions via photo SN1 process, a method that under some aspects rivals Pd-catalyzed reactions.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Albini, A. and Fagnoni, M., Green Chem. 6, 1–6 (2004).
Ciamician, G., Bull. Chem. Soc. Fr. [4] 3, i–xxvii (1908).
Griesbeck, A. G. and Mattay, J. (eds.), Synthetic Organic Photochemistry (Marcel Dekker, New York, 2005).
Horspool, W. and Lenci, F. (eds.), Organic Photochemistry and Photobiology, 2nd ed. (CRC Press, Boca Raton, FL, 2004).
Mattay, J. and Griesbeck, A. G. (eds.), Photochemical Key Steps in Organic Synthesis (VCH, Weinheim, 1994).
Bourissou, D., Guerret, O., Gabbai, F. P., and Bertrand, G., Chem. Rev. 100, 39–91 (2000).
Newcomb, M. and Manek, M. B., J. Am. Chem. Soc. 112, 9662–9663 (1990).
Panda, J. and Ghosh, S., Tetrahedron Lett. 40, 6693–6694 (1999).
Bunte, J. O., Rinne, S, and Mattay, J., Synthesis 619–621 (2004).
Schuster, G. B., Turro, N. J., Steinmetzer, H.-C., Schaap, A. P., Faler, G., Adam, W., and Liu, J. C., J. Am. Chem. Soc. 97, 7110–7118 (1975).
Cermenati, L., Mella, M, and Albini, A., Tetrahedron 54, 2575 (1998).
Ambroz, H. B. and Kemp, T., Chem. Soc. Rev. 8, 353–366 (1979).
Winkler, M. and Sander, W., Angew. Chem., Int. Ed. 39, 2014–2016 (2000).
Speranza, M., Tetrahedron Lett. 21, 1983 (1980).
Littke, A. F. and Fu, G. C., Angew. Chem., Int. Ed. 41, 4176–4211 (2002).
Stang, P. J. in Divalent Carbocations, edited by Rappoport, Z. and Stang, P. J. (Wiley, Chichester, 1997), pp. 451–460.
Gasper, S. M., Devadoss, C., and Schuster, G. B., J. Am. Chem. Soc. 117, 5206–5211 (1995).
Aschi, M. and Harvey, J. N., J. Chem. Soc., Perkin Trans. 2, 1059–1062 (1999).
Guizzardi, B., Mella, M., Fagnoni, M., Freccero, M., and Albini, A., J. Org. Chem. 66, 6353–6363 (2001).
Fagnoni, M. and Albini, A., Acc. Chem. Res. 38, 713–721 (2005).
Mella, M., Coppo, P., Guizzardi, B., Fagnoni, M., Freccero, M., and Albini, A., J. Org. Chem. 66, 6344–6352 (2001).
Coppo, P., Fagnoni, M., and Albini, A., Tetrahedron Lett. 42, 4271–4273 (2001).
Guizzardi, B., Mella, M., Fagnoni, M., and Albini, A., Chem. Eur. J. 9, 1549–1555 (2003).
Protti, S., Fagnoni, M., Mella, M., and Albini, A., J. Org. Chem. 69, 3465–3473 (2004).
Protti, S., Fagnoni, M., and Albini, A., Angew. Chem. Int. Ed. 44, 5875–5878 (2005).
Guizzardi, B., Mella, M., Fagnoni, M., and Albini, A., Tetrahedron 56, 9383–9390 (2000).
Milanesi, S., Fagnoni, M., and Albini, A., J. Org. Chem. 70, 603–610 (2005).
Protti, S., Fagnoni, M., and Albini, A., Org. Biomol. Chem. 3, 2868–2871 (2005).
Fraboni, A., Fagnoni, M., and Albini, A., J. Org. Chem. 68, 4886–4893 (2003).
Littke, A. F., Schwartz, L., and Fu, G. C., J. Am. Chem. Soc. 124, 6343–6347 (2002).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2008 Springer Science + Business Media B.V
About this paper
Cite this paper
Albini, A., Fagnoni, M. (2008). Photochemistry as a Green Synthetic Method. In: Mordini, A., Faigl, F. (eds) New Methodologies and Techniques for a Sustainable Organic Chemistry. NATO Science Series II: Mathematics, Physics and Chemistry, vol 246. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-6793-8_13
Download citation
DOI: https://doi.org/10.1007/978-1-4020-6793-8_13
Publisher Name: Springer, Dordrecht
Print ISBN: 978-1-4020-6791-4
Online ISBN: 978-1-4020-6793-8
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)