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
• Michael Oelgemöller ^{A E}

• ^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: [email protected]

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.

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