Skip to main content

Photochemical Synthesis

  • Chapter
  • First Online:
Applied Photochemistry

Abstract

Photochemical reactions are generally easily carried out, at least in laboratory scale, and require no expensive apparatus. Some general reactions, e.g. the cycloaddition of enones to alkenes and various oxygenations have been extensively investigated and represent an excellent choice for preparative applications. Many other possibilities are known—and a few are presented below. This suggests that photochemical steps should be considered more often in synthetic planning.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. White JD (1979). http://www.orgsyn.org/obits/buchi.pdf. Accessed 20 June 2012

  2. Albini A (2010) Photosciences: a look into the future. Photochem Photobiol Sci 9:1533–1534

    Article  CAS  Google Scholar 

  3. Griesbeck AJ (2009) Photochemistry of organic compounds. Angew Chemie Int Ed 48:4671–4672

    Article  CAS  Google Scholar 

  4. Albini A, Fagnoni M (eds) (2010) Handbook of preparative photochemistry. Wiley, Weinheim

    Google Scholar 

  5. Turro NJ, Ramamurthy V, Scaiano JC (2010) Modern molecular photochemistry of organic molecules. University Science Books, Herndon

    Google Scholar 

  6. Klàn P, Wirz J (2009) Photochemistry of organic compounds. From principles to practice. Wiley, Hoboken

    Book  Google Scholar 

  7. Saito H, Sivaguru J, Jockusch S et al (2007) Controlled diastereoselectivity at the alkene-geometry through selective encapsulation: E-Z photoisomerization of oxazolidinone-functionalized enecarbamates within hydrophobic nano-cavities. Chem Commun 43:819–821

    Google Scholar 

  8. Fuse S, Tanabe N, Yoshida M et al (2010) Continuous-flow synthesis of Vitamin D3. Chem Commun 46:8722–8724

    Article  CAS  Google Scholar 

  9. Yen CF, Liao CC (2002) Concise and efficient total synthesis of Lycopodium alkaloid Magellanine. Angew Chemie Int Ed 41:4090–4093

    Article  CAS  Google Scholar 

  10. Bach T, Spiegel A (2002) Stereoselective total synthesis of the tricyclic sesquiterpene (±)-Kelsoene by an intramolecular Cu(I)-catalyzed [2+2]-photocycloaddition reaction. Synlett: 1305–1307

    Google Scholar 

  11. Shipe WD, Sorensen EJ (2002) A convergent synthesis of the tricyclic architecture of the Guanacastepenes featuring a selective ring fragmentation. Org Lett 4:2063–2066

    Article  CAS  Google Scholar 

  12. Sarkar N, Nayek A, Ghosh S (2004) Copper(I)-catalyzed intramolecular asymmetric [2+2] photocycloaddition. Synthesis of both enantiomers of cyclobutane derivatives. Org Lett 6:1903–1905

    Article  CAS  Google Scholar 

  13. Zou J, Mariano PS (2008) The synthetic potential of pyridinium salt photochemistry. Photochem Photobiol Sci 7:393–404

    Article  CAS  Google Scholar 

  14. Zhao Z, Song L, Mariano PS (2005) A concise sequential photochemical-metathesis approach for the synthesis of (+)-Castanospermine and possible Uniflorine-A stereoisomers. Tetrahedron 61:8888–8894

    Article  CAS  Google Scholar 

  15. Gaich T, Mulzer J (2010) From Silphinenes to Penifulvins: a biomimetic approach to Penifulvins B and C. Org Lett 12:272–275

    Article  CAS  Google Scholar 

  16. Vaillard VA, Budén ME, Martín SE et al (2009) Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles. Tetrahedron Lett 50:3829–3832

    Article  CAS  Google Scholar 

  17. Fagnoni M, Albini A (2005) Arylation reactions. The SN1 path via phenyl cation as an alternative to metal catalysis. Acc Chem Res 38:713–721

    Article  CAS  Google Scholar 

  18. Ng D, Yang Z, Garcia-Garibay MA (2004) Total synthesis of (±)-Herbertenolide by stereospecific formation of vicinal quaternary centers in a crystalline ketone. Org Lett 6:645–647

    Article  CAS  Google Scholar 

  19. Natarajan A, Ng D, Yang Z et al (2007) Parallel syntheses of (+)- and (−)-α-Cuparenone by radical combination in crystalline solids. Angew Chem Int Ed 46:6485–6487

    Article  CAS  Google Scholar 

  20. Nicolaou KC, Gray DLF, Tae J (2003) Total synthesis of Hamigerans and analogues thereof. Photochemical generation and Diels-Alder trapping of hydroxy-o-quinodimethanes. J Am Chem Soc 126:613–627

    Article  Google Scholar 

  21. Pospíšil T, Veetil AT, Antony LAP et al (2008) Photochemical synthesis of substituted indan-1-ones related to Donepezil. Photochem Photobiol Sci 7:625–632

    Article  Google Scholar 

  22. Abe M, Terazawa M, Nozaki K, Masuyama A, Hayashi T (2006) Notable temperature effect on the stereoselectivity in the photochemical [2+2] cycloaddition reaction (Paternò–Büchi reaction) of 2,3-dihydrofuran-3-ol derivatives with benzophenone. Tetrahedron Lett 46:2527–2530

    Article  Google Scholar 

  23. Sugimoto A, Sumino Y, Takagi M et al (2006) The Barton reaction using a microreactor and black light. Continuous-flow synthesis of a key steroid intermediate for an endothelin receptor antagonist. Tetrahedron Lett 47:6197–6200

    Article  CAS  Google Scholar 

  24. Blay G, Bargues V, Cardona L et al (2000) Stereoselective synthesis of 7,11-guaien-8,12-olides from Santonin. Synthesis of Podoandin and (+)-Zedolactone A. J Org Chem 65:6703–6707

    Article  CAS  Google Scholar 

  25. Roy O, Faure S, Aitken DJ (2006) A solution to the component instability problem in the preparation of peptides containing C2-substituted cis-cyclobutane β-aminoacids: synthesis of a stable rhodopeptin analogue. Tetrahedron Lett 47:5981–5984

    Article  CAS  Google Scholar 

  26. Crimmins MT, Pace JM, Nantermet PG et al (2000) The total synthesis of (±)-Ginkgolide B. J Am Chem Soc 122:8453–8463

    Article  CAS  Google Scholar 

  27. Srikrishna A, Ramasastry SSV (2006) Enantiospecific first total synthesis of (+)-2β-hydroxysolanascone, the aglycone of the phytoalexin isolated from flue-cured tobacco leaves. Tetrahedron Lett 47:335–339

    Article  CAS  Google Scholar 

  28. Wootton RCR, Fortt R, de Mello AJ (2002) A microfabricated nanoreactor for safe, continuous generation and use of singlet oxygen. Org Process Res Dev 6:187–189

    Article  CAS  Google Scholar 

  29. Clennan EL, Pace A (2005) Advances in singlet oxygen chemistry. Tetrahedron 61:6665–6691

    Article  CAS  Google Scholar 

  30. Adam W, Bosio SG, Turro NJ (2002) Highly diastereoselective dioxetane formation in the photooxygenation of enecarbamates with an oxazolidinone chiral auxiliary: steric control in the [2+2] cycloaddition of singlet oxygen through conformational alignment. J Am Chem Soc 124:8814–8815

    Article  CAS  Google Scholar 

  31. Coyle EE, Joyce K, Nolan K, Oelgemöller M (2010) Green photochemistry: the use of microemulsions as green media in photooxygenation reactions. Green Chem 12:1544–1547

    Article  CAS  Google Scholar 

  32. Gassensmith JJ, Baumes JM, Eberhard J et al (2009) Cycloaddition to an anthracene-derived macrocyclic receptor with supramolecular control of regioselectivity. Chem Commun 45:2517–2519

    Google Scholar 

  33. Montagnon T, Tofi M, Vassilikogiannakis G (2008) Using singlet oxygen to synthesize polyoxygenated natural products from furans. Acc Chem Res 41:1001–1011

    Article  CAS  Google Scholar 

  34. Bailey S, Helliwell M, Teerawutgulrag A et al (2005) A total synthesis of Milbemycin G: approaches to the C(1)-C(10)-fragment and completion of the synthesis. Org Biomol Chem 3:3654–6477

    Article  CAS  Google Scholar 

  35. Pavlakos E, Georgiou T, Tofi M et al (2009) γ-Spiroketal γ-lactones from 2-(γ-hydroxyalkyl)furans: syntheses of epi-pyrenolides D and crassalactone D. Org Lett 11:4556–4559

    Article  CAS  Google Scholar 

  36. Mousli R, Tazerouti A (2011) Synthesis and some surface properties of glycine-based surfactants. J Surfact Deterg 14:65–72

    Article  CAS  Google Scholar 

  37. Podgoršek A, Stavber S, Zupan M et al (2009) Environmentally benign electrophilic and radical bromination ‘on water’: H2O2-HBr system versus N-bromosuccinimide. Tetrahedron 65:4429–4439

    Article  Google Scholar 

  38. Feldman KS, Ngernmeesri P (2005) Dragmacidin E synthesis studies. Preparation of a model heptacyclic core structure. Org Lett 7:5449–5451

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Angelo Albini .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2013 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Dichiarante, V., Albini, A. (2013). Photochemical Synthesis. In: Evans, R., Douglas, P., Burrow, H. (eds) Applied Photochemistry. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-3830-2_2

Download citation

Publish with us

Policies and ethics