Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
REVIEW

Recent Advances in Photodecarboxylations Involving Phthalimides

Saira Mumtaz A , Mark J. Robertson A and Michael Oelgemöller A B
+ Author Affiliations
- Author Affiliations

A James Cook University, College of Science and Engineering, Townsville, Qld 4811, Australia.

B Corresponding author. Email: michael.oelgemoeller@jcu.edu.au




Dr Saira Mumtaz received her M.Sc. in chemistry at Government College University in Lahore, Pakistan, in 2005 and her M.Phil. in organic chemistry from Bahauddin Zakariya University in Multan, Pakistan, in 2007. Between 2008 and 2012, she worked as a research assistant and guest lecturer at Bahauddin Zakariya University, Pakistan. From 2013 to 2017, she conduced her Ph.D. in organic photochemistry at James Cook University in Townsville, Australia. In 2018, she joined Nelson Mandala University in Port Elizabeth, South Africa, as a post-doctoral researcher.



Dr Mark Robertson received his Ph.D. in chemistry in 2002 from the University of Newcastle, Australia. He spent the following four years as a post-doctoral researcher at the University of Wollongong, Australia, on a project exploring peptoid antibiotics. After a career interruption spent in the secondary school system, he returned to a post-doctoral position at the University of Newcastle, Australia. In 2015, he began his independent research career as a senior lecturer at James Cook University, Australia, where his research interests include synthetic medicinal chemistry and the use of solar power to drive chemical reactions under flow conditions.



Associate Professor Michael Oelgemöller received his diploma from the University of Münster, Germany, in 1995 and his Ph.D. from the University of Cologne, Germany, in 1999. He was a researcher at the ERATO-JST Photochirogenesis project in Osaka (1999-2001), Japan, and at Bayer CropScience in Yuki (2001-2004), Japan. From 2004 to 2008, he was a lecturer in organic and medicinal chemistry at Dublin City University, Ireland. In February 2009, he joined James Cook University in Townsville, Australia, as Associate Professor in Organic Chemistry, where he leads the Applied and Green Photochemistry Research Group. His research interests range from the development of continuous-flow photoreactors to the solar manufacturing of chemicals, photochemical synthesis of bioactive compounds, photostability testing, and photochemical degradation of organic pollutants. He has received several awards and has been a visiting professor at various universities in Asia and Europe.

Australian Journal of Chemistry 71(9) 634-648 https://doi.org/10.1071/CH18220
Submitted: 14 May 2018  Accepted: 24 July 2018   Published: 21 August 2018

Abstract

Owing to their favourable photophysical and electrochemical properties, phthalimides undergo a variety of highly efficient photodecarboxylation reactions. These transformations have been applied to the synthesis of macrocyclic compounds as well as bioactive addition adducts. N-Acetoxyphthalimides are versatile precursors to imidyl and alkyl radicals through photodecarboxylation and have subsequently been used for a variety of coupling reactions. The generally mild reaction conditions make these reactions attractive for green chemical applications. The process protocols were successfully transferred to novel photoreactor devices, among these falling film or continuous flow reactors.


References

[1]  P. M. Lorz, F. K. Towae, W. Enke, R. Jäckh, N. Bhargava, W. Hillesheim, Ullmann’s Encycl. Ind. Chem. 2012, 27, 131.

[2]  N. Kushwaha, D. Kaushik, J. Appl. Pharm. Sci. 2016, 6, 159.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  J. Ashif, G. J. Sharma, S. Baranwal, M. S. Ahmad, Alam, Res. J. Pharm. Technol. 2013, 6, 711.

[4]  U. Sharma, P. Kumar, N. Kumar, B. Singh, Mini Rev. Med. Chem. 2010, 10, 678.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  C. J. Easton, C. A. Hutton, Synlett 1998, 457.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  G. H. L. Nefkens, G. I. Tesser, R. J. F. Nivard, Recl. Trav. Chim. Pays Bas 1960, 79, 688.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  Q. Zeng, Z. Liu, F. Wang, Amino Acids 2004, 27, 183.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  N. M. Ahmad, in Name Reactions for Functional Group Transformations (Eds J. J. Li, E. J. Corey) 2010, Ch. 5, pp. 438–450 (Wiley-Interscience: Hoboken, NJ).

[9]  J. H. Kim, A. R. Scialli, Toxicol. Sci. 2011, 122, 1.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  E. B. Gordon, in Hayes’ Handbook of Pesticide Toxicology 2010, 3rd edn, Ch. 90, pp. 1915–1949 (Elsevier Inc.: London).

[11]  M. Giardiello, T. O. McDonald, J.-S. Lee, A. D. Roberts, A. Owen, S. P. Rannard, Green Chem. 2013, 15, 1590.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  V. Wintgens, P. Valat, J. Kossanyi, L. Biczok, A. Demeter, T. Berces, J. Chem. Soc., Faraday Trans. 1994, 90, 411.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  A. G. Griesbeck, H. Görner, J. Photochem. Photobiol. Chem. 1999, 129, 111.
         | Crossref | GoogleScholarGoogle Scholar |

[14]  H. Hayashi, S. Nagakura, Y. Kubo, K. Maruyama, Chem. Phys. Lett. 1980, 72, 291.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  M. Oelgemöller, Chem. Rev. 2016, 116, 9664.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  D. W. Leedy, D. L. Muck, J. Am. Chem. Soc. 1971, 93, 4264.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  G. Farnia, A. Romanian, G. Capobianco, F. Torzo, J. Electroanal. Chem. Interfacial Electrochem. 1971, 33, 31.
         | Crossref | GoogleScholarGoogle Scholar |

[18]  G. Capobianco, G. Farnia, F. Torzo, Ric. Sci. 1968, 38, 842.

[19]  M. Oelgemöller, A. G. Griesbeck, J. Lex, A. Haeuseler, M. Schmittel, M. Niki, D. Hesek, Y. Inoue, Org. Lett. 2001, 3, 1593.
         | Crossref | GoogleScholarGoogle Scholar |

[20]  M. Oelgemöller, A. Haeuseler, M. Schmittel, A. G. Griesbeck, J. Lex, Y. Inoue, J. Chem. Soc., Perkin Trans. 2 2002, 676.
         | Crossref | GoogleScholarGoogle Scholar |

[21]  D. Rehm, A. Weller, Isr. J. Chem. 1970, 8, 259.
         | Crossref | GoogleScholarGoogle Scholar |

[22]  D. Rehm, A. Weller, Ber. Bunsenges. Phys. Chem 1969, 73, 834.

[23]  H. Görner, M. Oelgemöller, A. G. Griesbeck, J. Phys. Chem. A 2002, 106, 1458.
         | Crossref | GoogleScholarGoogle Scholar |

[24]  H. Görner, A. G. Griesbeck, T. Heinrich, W. Kramer, M. Oelgemöller, Chem. – Eur. J. 2001, 7, 1530.
         | Crossref | GoogleScholarGoogle Scholar |

[25]  A. G. Griesbeck, S. Schieffer, Photochem. Photobiol. Sci. 2003, 2, 113.
         | Crossref | GoogleScholarGoogle Scholar |

[26]  Y. Yoshimi, J. Synth. Org. Chem. Jpn. 2013, 71, 935.
         | Crossref | GoogleScholarGoogle Scholar |

[27]  D. Budac, P. Wan, J. Photochem. Photobiol. Chem. 1992, 67, 135.
         | Crossref | GoogleScholarGoogle Scholar |

[28]  Y. Yoshimi, J. Photochem. Photobiol. Chem. 2017, 342, 116.
         | Crossref | GoogleScholarGoogle Scholar |

[29]  J. Schwarz, B. König, Green Chem. 2018, 20, 323.
         | Crossref | GoogleScholarGoogle Scholar |

[30]  M. Martín-Flesia, A. Postigo, Curr. Org. Chem. 2012, 16, 2379.
         | Crossref | GoogleScholarGoogle Scholar |

[31]  D. H. R. Barton, S. Z. Zard, Pure Appl. Chem. 1986, 58, 675.
         | Crossref | GoogleScholarGoogle Scholar |

[32]  D. Crich, Aldrichim Acta 1987, 20, 35.

[33]  M. F. Saraiva, M. R. C. Couri, M. Le Hyaric, M. V. de Almeida, Tetrahedron 2009, 65, 3563.
         | Crossref | GoogleScholarGoogle Scholar |

[34]  Y. Sato, H. Nakai, T. Mizoguchi, M. Kawanishi, Y. Kanaoka, Chem. Pharm. Bull. 1973, 21, 176.
         | Crossref | GoogleScholarGoogle Scholar |

[35]  Y. Sato, H. Nakai, T. Mizoguchi, M. Kawanishi, Y. Hatanaka, Y. Kanaoka, Chem. Pharm. Bull. 1982, 30, 1262.

[36]  M. Horvat, K. Mlinarić-Majerski, N. Basarić, Croat. Chem. Acta 2010, 83, 179.

[37]  M. Oelgemöller, A. G. Griesbeck, J. Photochem. Photobiol. Photochem. Rev. 2002, 3, 109.
         | Crossref | GoogleScholarGoogle Scholar |

[38]  W. Kramer, A. G. Griesbeck, F. Nerowski, M. Oelgemöller, J. Inf. Rec. 1998, 24, 81.

[39]  G. McDermott, D. J. Yoo, M. Oelgemöller, Heterocycles 2005, 65, 2221.
         | Crossref | GoogleScholarGoogle Scholar |

[40]  A. G. Griesbeck, W. Kramer, M. Oelgemöller, Synlett 1999, 1169.
         | Crossref | GoogleScholarGoogle Scholar |

[41]  Y. Takahashi, T. Miyashi, U. C. Yoon, S. W. Oh, M. Mancheno, Z. Su, D. F. Falvey, P. S. Mariano, J. Am. Chem. Soc. 1999, 121, 3926.
         | Crossref | GoogleScholarGoogle Scholar |

[42]  U. C. Yoon, D. U. Kim, C. W. Lee, Y. S. Choi, Y.-J. Lee, H. L. Ammon, P. S. Mariano, J. Am. Chem. Soc. 1995, 117, 2698.
         | Crossref | GoogleScholarGoogle Scholar |

[43]  U. C. Yoon, S. W. Oh, S. M. Lee, S. J. Cho, J. Gamlin, P. S. Mariano, J. Org. Chem. 1999, 64, 4411.
         | Crossref | GoogleScholarGoogle Scholar |

[44]  U. C. Yoon, C. W. Lee, S. W. Oh, P. S. Mariano, Tetrahedron 1999, 55, 11997.
         | Crossref | GoogleScholarGoogle Scholar |

[45]  Q. Fang, L. Ding, W. Fang, Sci. China Chem. 2012, 55, 2090.

[46]  A. G. Griesbeck, J. Neudörfl, A. deKiff, Beilstein J. Org. Chem. 2011, 7, 518.
         | Crossref | GoogleScholarGoogle Scholar |

[47]  P. J. Wagner, Acc. Chem. Res. 1983, 16, 461.
         | Crossref | GoogleScholarGoogle Scholar |

[48]  A. G. Griesbeck, A. Henz, W. Kramer, J. Lex, F. Nerowski, M. Oelgemöller, K. Peters, E.-M. Peters, Helv. Chim. Acta 1997, 80, 912.
         | Crossref | GoogleScholarGoogle Scholar |

[49]  A. G. Griesbeck, F. Nerowski, J. Lex, J. Org. Chem. 1999, 64, 5213.
         | Crossref | GoogleScholarGoogle Scholar |

[50]  M. Horvat, K. Mlinarić-Majerski, A. G. Griesbeck, N. Basarić, Photochem. Photobiol. Sci. 2011, 10, 610.
         | Crossref | GoogleScholarGoogle Scholar |

[51]  L. Mandić, K. Mlinarić-Majerski, A. G. Griesbeck, N. Basarić, Eur. J. Org. Chem. 2016, 4404.
         | Crossref | GoogleScholarGoogle Scholar |

[52]  D. J. Yoo, E. Y. Kim, M. Oelgemöller, S. C. Shim, Heterocycles 2001, 54, 1049.
         | Crossref | GoogleScholarGoogle Scholar |

[53]  D. J. Yoo, E. Y. Kim, M. Oelgemöller, S. C. Shim, Photochem. Photobiol. Sci. 2004, 3, 311.
         | Crossref | GoogleScholarGoogle Scholar |

[54]  U. C. Yoon, C. W. Lee, S. W. Oh, H. J. Kim, S. J. Lee, J. Photosci. 2000, 7, 143.

[55]  A. R. Kim, K. Lee, C. Lee, D. J. Yoo, F. Hatoum, M. Oelgemöller, Tetrahedron Lett. 2005, 46, 3395.
         | Crossref | GoogleScholarGoogle Scholar |

[56]  Y. Lee, D. Ahn, K. Lee, A. R. Kim, D. J. Yoo, M. Oelgemöller, Tetrahedron Lett. 2011, 52, 5029.
         | Crossref | GoogleScholarGoogle Scholar |

[57]  A. R. Kim, H. Cho, Y. Lee, D. J. Yoo, Bull. Korean Chem. Soc. 2012, 33, 3477.
         | Crossref | GoogleScholarGoogle Scholar |

[58]  U. C. Yoon, S. J. Lee, S. W. Oh, D. W. Cho, J. Photosci. 2001, 8, 99.

[59]  A. G. Griesbeck, M. Oelgemöller, J. Lex, A. Haeuseler, M. Schmittel, Eur. J. Org. Chem. 2001, 1831.
         | Crossref | GoogleScholarGoogle Scholar |

[60]  K. Peters, E.-M. Peters, M. Oelgemöller, A. G. Griesbeck, Z. Kristallogr. NCS 1998, 213, 757.
         | Crossref | GoogleScholarGoogle Scholar |

[61]  U. C. Yoon, Y. X. Jin, S. W. Oh, C. H. Park, J. H. Park, C. F. Campana, X. Cai, E. N. Duesler, P. S. Mariano, J. Am. Chem. Soc. 2003, 125, 10664.
         | Crossref | GoogleScholarGoogle Scholar |

[62]  G. Tan, S. Wei, J. Zhao, P. Zhang, B. Wang, P. Zheng, Y. Liu, Y. Jin, Imag. Sci. Photochem. 2010, 28, 131.

[63]  C. Dong, G. Tan, Y. Jin, Youji Huaxue 2014, 34, 578.
         | Crossref | GoogleScholarGoogle Scholar |

[64]  A. G. Griesbeck, T. Heinrich, M. Oelgemöller, A. Molis, A. Heidtmann, Helv. Chim. Acta 2002, 85, 4561.
         | Crossref | GoogleScholarGoogle Scholar |

[65]  A. G. Griesbeck, T. Heinrich, M. Oelgemöller, A. Molis, J. Lex, J. Am. Chem. Soc. 2002, 124, 10972.
         | Crossref | GoogleScholarGoogle Scholar |

[66]  K. Krüger, V. Lüdke, J. Pettinger, L. Ashton, L. Bonnet, C. A. Motti, J. Lex, M. Oelgemöller, Tetrahedron Lett. 2018, 59, 1427.
         | Crossref | GoogleScholarGoogle Scholar |

[67]  H. Takechi, M. Machida, Y. Kanaoka, Liebigs Ann. Chem. 1986, 859.
         | Crossref | GoogleScholarGoogle Scholar |

[68]  A. G. Griesbeck, W. Kramer, J. Lex, Angew. Chem. Int. Ed. Engl. 2001, 40, 577.
         | Crossref | GoogleScholarGoogle Scholar |

[69]  A. G. Griesbeck, W. Kramer, J. Lex, Synthesis 2001, 1159.

[70]  A. G. Griesbeck, W. Kramer, T. Heinrich, J. Lex, Photochem. Photobiol. Sci. 2002, 1, 237.
         | Crossref | GoogleScholarGoogle Scholar |

[71]  A. G. Griesbeck, W. Kramer, A. Bartoschek, H. Schmickler, Org. Lett. 2001, 3, 537.
         | Crossref | GoogleScholarGoogle Scholar |

[72]  M. Sohora, T. Š. Ramljak, K. Mlinarić-Majerski, N. Basarić, Croat. Chem. Acta 2014, 87, 431.
         | Crossref | GoogleScholarGoogle Scholar |

[73]  Š. T. Ramljak, M. Sohora, I. Antol, D. Kontrec, N. Basarić, K. Mlinarić-Majerski, Tetrahedron Lett. 2014, 55, 4078.
         | Crossref | GoogleScholarGoogle Scholar |

[74]  M. Sohora, N. Vidović, K. Mlinarić-Majerski, N. Basarić, Res. Chem. Intermed. 2017, 43, 5305.
         | Crossref | GoogleScholarGoogle Scholar |

[75]  A. G. Griesbeck, M. Oelgemöller, Synlett 1999, 492.
         | Crossref | GoogleScholarGoogle Scholar |

[76]  A. G. Griesbeck, M. Oelgemöller, J. Lex, Synlett 2000, 1455.
         | Crossref | GoogleScholarGoogle Scholar |

[77]  A. G. Griesbeck, M. S. Gudipati, J. Hirt, J. Lex, M. Oelgemöller, H. Schmickler, F. Schouren, J. Org. Chem. 2000, 65, 7151.
         | Crossref | GoogleScholarGoogle Scholar |

[78]  A. G. Griesbeck, N. Nazarow, J. M. Neudörfl, M. Heffen, Green Chem. 2012, 14, 3004.
         | Crossref | GoogleScholarGoogle Scholar |

[79]  A. G. Griesbeck, J.-M. Neudörfl, B. Goldfuss, S. Molitor, ChemPhotoChem 2017, 1, 355.
         | Crossref | GoogleScholarGoogle Scholar |

[80]  M. Oelgemöller, P. Cygon, J. Lex, A. G. Griesbeck, Heterocycles 2003, 59, 669.
         | Crossref | GoogleScholarGoogle Scholar |

[81]  A. G. Griesbeck, K. Warzecha, J. M. Neudörfl, H. Görner, Synlett 2004, 2347.
         | Crossref | GoogleScholarGoogle Scholar |

[82]  K.-D. Warzecha, H. Görner, A. G. Griesbeck, J. Phys. Chem. A 2006, 110, 3356.
         | Crossref | GoogleScholarGoogle Scholar |

[83]  F. Hatoum, S. Gallagher, L. Baragwanath, J. Lex, M. Oelgemöller, Tetrahedron Lett. 2009, 50, 6335.
         | Crossref | GoogleScholarGoogle Scholar |

[84]  V. Belluau, P. Noeureuil, E. Ratzke, A. Skvortsov, S. Gallagher, C. A. Motti, M. Oelgemöller, Tetrahedron Lett. 2010, 51, 4738.
         | Crossref | GoogleScholarGoogle Scholar |

[85]  H. M. Pordanjani, C. Faderl, J. Wang, C. A. Motti, P. C. Junk, M. Oelgemöller, Aust. J. Chem. 2015, 68, 1662.
         | Crossref | GoogleScholarGoogle Scholar |

[86]  F. Hatoum, J. Engler, C. Zelmer, J. Wißen, C. A. Motti, J. Lex, M. Oelgemöller, Tetrahedron Lett. 2012, 53, 5573.
         | Crossref | GoogleScholarGoogle Scholar |

[87]  O. Anamimoghadam, S. Mumtaz, A. Nietsch, G. Saya, C. A. Motti, P. C. Junk, A. M. Qureshi, M. Oelgemöller, Beilstein J. Org. Chem. 2017, 13, 2833.
         | Crossref | GoogleScholarGoogle Scholar |

[88]  S. Gallagher, F. Hatoum, N. Zientek, M. Oelgemöller, Tetrahedron Lett. 2010, 51, 3639.
         | Crossref | GoogleScholarGoogle Scholar |

[89]  F. Hatoum, S. Gallagher, M. Oelgemöller, Tetrahedron Lett. 2009, 50, 6593.
         | Crossref | GoogleScholarGoogle Scholar |

[90]  M. D. Kärkäs, ACS Catal. 2017, 7, 4999.
         | Crossref | GoogleScholarGoogle Scholar |

[91]  G. Pratsch, G. L. Lackner, L. E. Overman, J. Org. Chem. 2015, 80, 6025.
         | Crossref | GoogleScholarGoogle Scholar |

[92]  K. Okada, K. Okamoto, M. Oda, J. Am. Chem. Soc. 1988, 110, 8736.
         | Crossref | GoogleScholarGoogle Scholar |

[93]  K. Okada, K. Okubo, N. Morita, M. Oda, Tetrahedron Lett. 1992, 33, 7377.
         | Crossref | GoogleScholarGoogle Scholar |

[94]  K. Okada, K. Okamoto, M. Oda, J. Chem. Soc. Chem. Commun. 1989, 1636.
         | Crossref | GoogleScholarGoogle Scholar |

[95]  M. Cano, G. Fabriàs, F. Camps, J. Joglar, Tetrahedron Lett. 1998, 39, 1079.
         | Crossref | GoogleScholarGoogle Scholar |

[96]  L. J. Allen, P. J. Cabrera, M. Lee, M. S. Sanford, J. Am. Chem. Soc. 2014, 136, 5607.
         | Crossref | GoogleScholarGoogle Scholar |

[97]  L. M. Kammer, A. Rahman, T. Opatz, Molecules 2018, 23, 764.
         | Crossref | GoogleScholarGoogle Scholar |

[98]  W.-M. Cheng, R. Shang, Y. Fu, ACS Catal. 2017, 7, 907.
         | Crossref | GoogleScholarGoogle Scholar |

[99]  K. Okada, K. Okamoto, N. Morita, K. Okubo, M. Oda, J. Am. Chem. Soc. 1991, 113, 9401.
         | Crossref | GoogleScholarGoogle Scholar |

[100]  G. L. Lackner, K. W. Quasdorf, L. E. Overman, J. Am. Chem. Soc. 2013, 135, 15342.
         | Crossref | GoogleScholarGoogle Scholar |

[101]  A. Tlahuext-Aca, R. A. Garza-Sanchez, F. Glorius, Angew. Chem. Int. Ed. 2017, 56, 3708.
         | Crossref | GoogleScholarGoogle Scholar |

[102]  K. Xu, Z. Tan, H. Zhang, J. Liu, S. Zhang, Z. Wang, Chem. Commun. 2017, 10719.
         | Crossref | GoogleScholarGoogle Scholar |

[103]  J.-C. Yang, J.-Y. Zhang, J.-J. Zhang, X.-H. Duan, L.-N. Guo, J. Org. Chem. 2018, 83, 1598.
         | Crossref | GoogleScholarGoogle Scholar |

[104]  G. Kachkovskyi, C. Faderl, O. Reiser, Adv. Synth. Catal. 2013, 355, 2240.
         | Crossref | GoogleScholarGoogle Scholar |

[105]  J. Schwarz, B. König, ChemPhotoChem 2017, 1, 237.
         | Crossref | GoogleScholarGoogle Scholar |

[106]  L. Candish, M. Teders, F. Glorius, J. Am. Chem. Soc. 2017, 139, 7440.
         | Crossref | GoogleScholarGoogle Scholar |

[107]  W.-M. Cheng, R. Shang, B. Zhao, W.-L. Xing, Y. Fu, Org. Lett. 2017, 19, 4291.
         | Crossref | GoogleScholarGoogle Scholar |

[108]  L. Candish, L. Pitzer, A. Gómez-Suárez, F. Glorius, Chem. – Eur. J. 2016, 22, 4753.
         | Crossref | GoogleScholarGoogle Scholar |

[109]  M. Jiang, H. Yang, H. Fu, Org. Lett. 2016, 18, 1968.
         | Crossref | GoogleScholarGoogle Scholar |

[110]  A. Soldevilla, A. G. Griesbeck, J. Am. Chem. Soc. 2006, 128, 16472.
         | Crossref | GoogleScholarGoogle Scholar |

[111]  A. Soldevilla, R. Pérez-Ruiz, Y. D. Miara, A. G. Griesbeck, Chem. Commun. 2010, 3747.
         | Crossref | GoogleScholarGoogle Scholar |

[112]  K. Arimitsu, K. Fukuda, N. Sakai, Chem. Lett. 2014, 43, 831.
         | Crossref | GoogleScholarGoogle Scholar |

[113]  M. He, G. Chen, X. Huang, R. Xu, Z. Zenga, J. Yang, Polym. Chem. 2014, 5, 2951.
         | Crossref | GoogleScholarGoogle Scholar |

[114]  A. G. Griesbeck, W. Kramer, M. Oelgemöller, Green Chem. 1999, 1, 205.
         | Crossref | GoogleScholarGoogle Scholar |

[115]  A. G. Griesbeck, N. Maptue, S. Bondock, M. Oelgemöller, Photochem. Photobiol. Sci. 2003, 2, 450.
         | Crossref | GoogleScholarGoogle Scholar |

[116]  K. Mizuno, Y. Nishiyama, T. Ogaki, K. Terao, H. Ikeda, K. Kakiuchi, J. Photochem. Photobiol. Photochem. Rev. 2016, 29, 107.
         | Crossref | GoogleScholarGoogle Scholar |

[117]  V. D. Pinho, L. S. M. Miranda, R. O. M. A. de Souza, Rev. Virtual Quim. 2015, 7, 144.
         | Crossref | GoogleScholarGoogle Scholar |

[118]  M. Oelgemöller, N. Hoffmann, O. Shvydkiv, Aust. J. Chem. 2014, 67, 337.
         | Crossref | GoogleScholarGoogle Scholar |

[119]  K. Gilmore, P. H. Seeberger, Chem. Rec. 2014, 14, 410.
         | Crossref | GoogleScholarGoogle Scholar |

[120]  E. E. Coyle, M. Oelgemöller, Photochem. Photobiol. Sci. 2008, 7, 1313.
         | Crossref | GoogleScholarGoogle Scholar |

[121]  M. Oelgemöller, Chem. Eng. Technol. 2012, 35, 1144.
         | Crossref | GoogleScholarGoogle Scholar |

[122]  M. Oelgemöller, O. Shvydkiv, Molecules 2011, 16, 7522.
         | Crossref | GoogleScholarGoogle Scholar |

[123]  M. Oelgemöller, T. Goodine, P. Malakar, in Sustainable Flow Chemistry – Methods and Applications (Ed. L. Vaccaro) 2017, Ch. 1, pp. 1–24 (Wiley-VCH: Weinheim).

[124]  O. Shvydkiv, S. Gallagher, K. Nolan, M. Oelgemöller, Org. Lett. 2010, 12, 5170.
         | Crossref | GoogleScholarGoogle Scholar |

[125]  M. Oelgemöller, S. Gallagher, K. McCarthy, Processes 2014, 2, 158.
         | Crossref | GoogleScholarGoogle Scholar |

[126]  O. Shvydkiv, K. Nolan, M. Oelgemöller, Beilstein J. Org. Chem. 2011, 7, 1055.
         | Crossref | GoogleScholarGoogle Scholar |

[127]  S. Josland, S. Mumtaz, M. Oelgemöller, Chem. Eng. Technol. 2016, 39, 81.
         | Crossref | GoogleScholarGoogle Scholar |

[128]  L. D. Elliott, M. Berry, B. Harji, D. Klauber, J. Leonard, K. I. Booker-Milburn, Org. Process Res. Dev. 2016, 20, 1806.
         | Crossref | GoogleScholarGoogle Scholar |

[129]  E. N. DeLaney, D. S. Lee, L. D. Elliott, J. Jin, K. I. Booker-Milburn, M. Poliakoff, M. W. George, Green Chem. 2017, 19, 1431.
         | Crossref | GoogleScholarGoogle Scholar |

[130]  M. Oelgemöller, J. Chin. Chem. Soc. 2014, 61, 743.
         | Crossref | GoogleScholarGoogle Scholar |

[131]  M. Pagliaro, Chim. Oggi – Chem. Today 2017, 35, 84.

[132]  M. Oelgemöller, M. Bolte, Green Process Synth. 2014, 3, 163.
         | Crossref | GoogleScholarGoogle Scholar |