Free Standard AU & NZ Shipping For All Book Orders Over $80!
Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH15356
RESEARCH ARTICLE
Contents Vol 68(11)

Photodecarboxylative Benzylations of N-Methoxyphthalimide under Batch and Continuous-Flow Conditions

Hossein Mohammadkhani Pordanjani A B , Christian Faderl A C , Jun Wang A , Cherie A. Motti D , Peter C. Junk A and Michael Oelgemöller A E
+ Author Affiliations
- Author Affiliations

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

B Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran.

C Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, D-93053 Regensburg, Germany.

D Australian Institute of Marine Science (AIMS), Biomolecular Analysis Facility, Townsville, Qld 4810, Australia.

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

Australian Journal of Chemistry 68(11) 1662-1667 https://doi.org/10.1071/CH15356
Submitted: 16 June 2015  Accepted: 20 July 2015   Published: 25 August 2015

Abstract

A series of photodecarboxylative benzylations of N-methoxyphthalimide were successfully realised using easily accessible starting materials. The reactions proceeded smoothly and the corresponding benzylated hydroxyphthalimidines were obtained in moderate to good yields of 52–73 %. No competing photoinduced dealkoxylation of the N-methoxy group was observed. The reaction with potassium phenylacetate was subsequently investigated in an advanced continuous-flow photoreactor. The reactor allowed rapid optimization of the reaction conditions and gave the desired benzylated product in higher yield and shorter irradiation time compared with the batch process.


References

[1]  F. Csende, F. Miklós, G. Stájer, Curr. Org. Chem. 2012, 16, 1005.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xms1egt7g%3D&md5=1e7a803cad0821a2837d2a58726c0200CAS |

[2]  Y. Kato, M. Takemoto, K. Achiwa, Chem. Pharm. Bull. (Tokyo) 1999, 47, 529.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXislSku7g%3D&md5=a6d0c027b34188171bb40160589e044bCAS | 10319431PubMed |

[3]  Y. Kato, H. Tebiike, K. Achiwa, N. Ashizawa, T. Kurihara, F. Kobayashi, Chem. Pharm. Bull. (Tokyo) 1990, 38, 2060.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXkt1Cksg%3D%3D&md5=0ddc5eab49afe6e70e48cfe6945bcca5CAS | 2268913PubMed |

[4]  A. Marsili, Eur. Patent EP-0105131A1 1983 [Chem. Abstr. 1984, 101, 54922].

[5]  N. Kise, Y. Kawano, T. Sakurai, J. Org. Chem. 2013, 78, 12453.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhvVamsb7J&md5=6c76abf6d22e74b03991657ebd6a3c15CAS | 24266907PubMed |

[6]  J. Ju, C. Qi, L. Zheng, R. Hua, Tetrahedron Lett. 2013, 54, 5159.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXht1Sjt7vK&md5=e1ff76473967f92d815c1bbf2ad87c00CAS |

[7]  M. A. Reyes-González, A. Zamudio-Medina, M. Ordóñez, Tetrahedron Lett. 2012, 53, 5756.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  F. M. Irudayanathan, J. Noh, J. Choi, S. Lee, Adv. Synth. Catal. 2014, 356, 3433.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhsVyrs7nK&md5=66b4e2c6b71cff26e67a897ed74f23fcCAS |

[9]  A. Gogoi, S. Guin, S. K. Rout, G. Majji, B. K. Patel, RSC Adv. 2014, 4, 59902.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhvVGhsbrK&md5=996f261bf6b369b94ee16935b730b197CAS |

[10]  A. Bubar, P. Estey, M. Lawson, S. Eisler, J. Org. Chem. 2012, 77, 1572.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XivVenuw%3D%3D&md5=cd1443a3135578dbe7510b0f9052f426CAS | 22283558PubMed |

[11]  A. G. Griesbeck, W. Kramer, M. Oelgemöller, Synlett 1999, 1169.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXksVCltbY%3D&md5=759f0d5c5a2788163ad30e73c0ab678cCAS |

[12]  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 | 1:CAS:528:DyaK2sXjs1Khs7o%3D&md5=d2ffa0fd41972e8573a9aa0cf25eac9dCAS |

[13]  F. Hatoum, J. Engler, C. Zelmer, J. Wißen, C. A. Motti, J. Lex, M. Oelgemöller, Tetrahedron Lett. 2012, 53, 5573.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xht12lsLrK&md5=d4cd3932f6bb3c02076914922550ae4aCAS |

[14]  V. Belluau, P. Noeureuil, E. Ratzke, A. Skvortsov, S. Gallagher, C. A. Motti, M. Oelgemöller, Tetrahedron Lett. 2010, 51, 4738.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXpvFKgs7g%3D&md5=7c11d5fc06c4a3c0a7a92f3c6d75ef01CAS |

[15]  F. Hatoum, S. Gallagher, L. Baragwanath, J. Lex, M. Oelgemöller, Tetrahedron Lett. 2009, 50, 6335.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1amtbfK&md5=bb75514c9c0385e29a338fa816df2c38CAS |

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

[17]  D. Budac, P. Wan, J. Photochem. Photobiol. Chem. 1992, 67, 135.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXitFOgtg%3D%3D&md5=575fd9eb664ef7202d73d5b7e49aab02CAS |

[18]  Y. Yoshimi, J. Synth. Org. Chem. Jpn. 2013, 71, 935.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhsFWku7nI&md5=4b711c3a9cad046fe924fe978fa928c0CAS |

[19]  Y. Yoshimi, M. Masuda, T. Mizunashi, K. Nishikawa, K. Maeda, N. Koshida, T. Itou, T. Morita, M. Hatanaka, Org. Lett. 2009, 11, 4652.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtFaltLjJ&md5=64be1dba5412cd06681f1cd2cea7d72aCAS | 19751053PubMed |

[20]  S. Kim, T. A. Lee, Y. Song, Synlett 1998, 471.
         | Crossref | GoogleScholarGoogle Scholar |

[21]  G. L. Lackner, K. W. Quasdorf, L. E. Overman, J. Am. Chem. Soc. 2013, 135, 15342.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhsFars77E&md5=85eb3a888592d2fb6a4e263c949a3b12CAS | 24074152PubMed |

[22]  G. Kachkovskyi, C. Faderl, O. Reiser, Adv. Synth. Catal. 2013, 355, 2240.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXht1OiurvE&md5=7e48ea4d4ff4ae67eee12ce4e36b6d04CAS |

[23]  K. Okada, K. Okubo, N. Morita, M. Oda, Tetrahedron Lett. 1992, 33, 7377.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXhsVKqsb8%3D&md5=b9bbc5436d1632f958ecb43bc89711fdCAS |

[24]  K. Okada, K. Okamoto, N. Morita, K. Okubo, M. Oda, J. Am. Chem. Soc. 1991, 113, 9401.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXmsl2jtLg%3D&md5=0f626a46c3e958988133d3a7f889c333CAS |

[25]  K. Okada, K. Okamoto, M. Oda, J. Chem. Soc., Chem. Commun. 1989, 1636.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXhvFyjsLw%3D&md5=95e4cc3bda0e901d332e3ac51da66852CAS |

[26]  M. Zlotorzynska, G. M. Sammis, Org. Lett. 2011, 13, 6264.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsVaisLbK&md5=05bff354b75b52bc396defb575e0b994CAS | 22060120PubMed |

[27]  M. Zlotorzynska, H. Zhai, G. M. Sammis, Org. Lett. 2008, 10, 5083.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXht1Cgsb7E&md5=6d8eaa3acb9c64c9d147f48ee08cf5b7CAS | 18855396PubMed |

[28]  M. Lucarini, F. Ferroni, G. F. Pedulli, S. Gardi, D. Lazzari, G. Schlingloff, Tetrahedron 2007, 48, 5331.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXntF2mtLk%3D&md5=58b6a14012ff8aac7bc2fad1b6ec1ebdCAS |

[29]  A. M. Al-Etaibi, N. A. Al-Awadi, M. R. Ibrahim, Y. A. Ibrahim, ARKIVOC 2010, 2010, 149.
         | Crossref | GoogleScholarGoogle Scholar |

[30]  M. Montalti, A. Credi, L. Prodi, M. T. Gandolfi, Handbook of Photochemistry, 3rd edn 2006 (CRC Press: Boca Rotan, FL).

[31]  K. K. Athankar, K. L. Wasewar, M. N. Varma, D. Z. Shende, J. Ind. Eng. Chem. 2015, 22, 240.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtlart77E&md5=3e6bb35a38db0df82a748147f156a0a0CAS |

[32]  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 | 11405663PubMed |

[33]  H. Yokoi, T. Nakano, W. Fujita, K. Ishiguro, Y. Sawaki, J. Am. Chem. Soc. 1998, 120, 12453.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXntl2qsrc%3D&md5=91e6cc45289e38faa0363ef03a1c74b1CAS |

[34]  Y. Yoshimi, T. Itou, M. Hatanaka, Chem. Commun. 2007, 5244.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtl2gs73P&md5=c51f39a0cc6e2c49835a7fdffd324ccaCAS |

[35]  H. Nakai, Y. Sato, T. Mizoguchi, Y. Kanaoka, Synthesis 1982, 141.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL38XhvVSrtbs%3D&md5=9cdf753fe7d71de8849bab8c89a07b59CAS |

[36]  K.-D. Warzecha, H. Görner, A. G. Griesbeck, J. Phys. Chem. A 2006, 110, 3356.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtFKntbo%3D&md5=a0b4d5230ae1e04cf7f77d02f86c3d0bCAS | 16526613PubMed |

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

[38]  H. Görner, A. G. Griesbeck, T. Heinrich, W. Kramer, M. Oelgemöller, Chem. – Eur. J. 2001, 7, 1530.
         | Crossref | GoogleScholarGoogle Scholar | 11330909PubMed |

[39]  D. W. Manley, J. C. Walton, Org. Lett. 2014, 16, 5394.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhslahsLzO&md5=40fdb76428d07d8091b3dc8cd606ab5fCAS | 25290736PubMed |

[40]  D. W. Manley, R. T. McBurney, P. Miller, R. F. Howe, S. Rhydderch, J. C. Walton, J. Am. Chem. Soc. 2012, 134, 13580.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtFGjsr%2FN&md5=158ca8d608a52b153f73c9976b46c7bfCAS | 22867432PubMed |

[41]  V. D. Pinho, L. S. M. Miranda, R. O. M. A. de Souza, Rev. Virtual Quim. 2015, 7, 144.

[42]  K. Gilmore, P. H. Seeberger, Chem. Rec. 2014, 14, 410.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXovVKnsro%3D&md5=c6772af80f79785ed4b87acdd154ff7eCAS | 24890908PubMed |

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

[44]  E. E. Coyle, M. Oelgemöller, Photochem. Photobiol. Sci. 2008, 7, 1313.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtlWjtb7J&md5=2ac258a3f43d7a86c19e9dc19e7aa0d8CAS | 18958317PubMed |

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

[46]  O. Shvydkiv, K. Nolan, M. Oelgemöller, Beilstein J. Org. Chem. 2011, 7, 1055.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtFSktLvE&md5=4e27e5a4feb6bdc973b18e1483848bb9CAS | 21915208PubMed |

[47]  O. Shvydkiv, S. Gallagher, K. Nolan, M. Oelgemöller, Org. Lett. 2010, 12, 5170.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXht1yktL%2FI&md5=8e22511c3edfb225cb16bc5d939ccb2bCAS | 20945889PubMed |

[48]  A. G. Griesbeck, N. Maptue, S. Bondock, Photochem. Photobiol. Sci. 2003, 2, 450.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXis12qs7o%3D&md5=72e7f93d3622fe70a64947d5a1c10e5dCAS |

[49]  A. G. Griesbeck, W. Kramer, M. Oelgemöller, Green Chem. 1999, 1, 205.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXls1ehtbk%3D&md5=1025deee061a288eb1f813ee4eb1b0cdCAS |

[50]  O. Shvydkiv, A. Yavorskyy, S. B. Tan, K. Nolan, N. Hoffmann, A. Youssef, M. Oelgemöller, Photochem. Photobiol. Sci. 2011, 10, 1399.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtVOktLnE&md5=aeea43006aa88d7b449348519608e577CAS | 21336374PubMed |

[51]  A. M. Braun, M. Maurette, E. Oliveros, Photochemical Technology 1991 (Wiley: Chichester).

[52]  T. Aillet, K. Loubiere, O. Dechy-Cabaret, L. Prat, Chem. Eng. Process. 2013, 64, 38.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhvVyrtL%2FI&md5=14fde2d140b84ebd99f567276c17343cCAS |

[53]  T. Yamashita, M. Inoue, M. Yasuda, Bull. Chem. Soc. Jpn. 2015, 88, 562.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXns1Sqt7s%3D&md5=2d9e34dd4005ffd23e06e0df6002d018CAS |

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

[55]  G. McDermott, D. J. Yoo, M. Oelgemöller, Heterocycles 2005, 65, 2221.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtVWisrbL&md5=b0c6402f396b0b62947c820253a95338CAS |

[56]  M. Horvat, K. Mlinarić-Majerski, N. Basarić, Croat. Chem. Acta 2010, 83, 179.
         | 1:CAS:528:DC%2BC3cXhtVejtrjJ&md5=2d12859f85a05f26f89cdf2af6ff0a95CAS |

[57]  F. Hatoum, S. Gallagher, M. Oelgemöller, Tetrahedron Lett. 2009, 50, 6593.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1Gmsb%2FE&md5=a487cc35d1f8ddb95da496a4a53f20bdCAS |

[58]  S. Gallagher, F. Hatoum, N. Zientek, M. Oelgemöller, Tetrahedron Lett. 2010, 51, 3639.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXnsVWhtL4%3D&md5=eba717f2dc47a5d7ff92dc7a25a1bce3CAS |

[59]  R. A. Jackson, M. Sharifi, J. Chem. Soc., Perkin Trans. 2 1996, 2, 775.
         | Crossref | GoogleScholarGoogle Scholar |

[60]  P. Chin, W. S. Barney, B. A. Pindzola, Curr. Opin. Drug Discovery Dev. 2009, 12, 848.
         | 1:CAS:528:DC%2BD1MXhsFSku7vI&md5=b10184a57c703d1a6c307c252823ffd6CAS |

[61]  D. M. Roberge, B. Zimmermann, F. Rainone, M. Gottsponer, M. Eyholzer, N. Kockmann, Org. Process Res. Dev. 2008, 12, 905.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtVWmu7nM&md5=d2bc063adf1e1a67a224388dea28899eCAS |

[62]  A. Yavorskyy, O. Shvydkiv, N. Hoffmann, K. Nolan, M. Oelgemöller, Org. Lett. 2012, 14, 4342.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xht1Wqu7zO&md5=99b2d642ea10662a5c59e66eb2a2e35aCAS | 22905680PubMed |

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

[64]  S. Josland, S. Mumtaz, M. Oelgemöller, Chem. Eng. Technol. 2015, 38, in press
         | Crossref | GoogleScholarGoogle Scholar |

[65]  G. E. Batley, Anal. Chem. 1984, 56, 2261.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXlsVaqs70%3D&md5=937a9436cde109af8d11fc803779a71dCAS |

[66]  H. D. Flack, Acta Crystallogr. Sect. A: Found. Crystallogr. 1983, 39, 876.
         | Crossref | GoogleScholarGoogle Scholar |