Photodecarboxylative benzylations of N-methoxyphthalimide under batch and continuous-flow conditions

Journal Publication ResearchOnline@JCU
Mohammadkhani Pordanjani, Hossein;Faderl, Christian;Wang, Jun;Motti, Cherie D.;Junk, Peter C.;Oelgemöller, Michael
Abstract

A series of photodecarboxylative benzylations of N-methoxyphthalimide were successfully realized 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.

Journal

Australian Journal of Chemistry

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Volume

68

ISBN/ISSN

1445-0038

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Issue

11

Pages Count

6

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Publisher

CSIRO Publishing

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EISSN

N/A

DOI

10.1071/CH15356