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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.


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