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

Mohammadkhani Pordanjani, Hossein, Faderl, Christian, Wang, Jun, Motti, Cherie D., Junk, Peter C., and Oelgemöller, Michael (2015) Photodecarboxylative benzylations of N-methoxyphthalimide under batch and continuous-flow conditions. Australian Journal of Chemistry, 68 (11). pp. 1662-1667.

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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.

Item ID: 41120
Item Type: Article (Refereed Research - C1)
Keywords: photodecarboxylation; flow photochemistry; benzylation; microreactor
ISSN: 1445-0038
Funders: Australian Research Council (ARC), James Cook University (JCU)
Projects and Grants: ARC DP130100794, JCU RIBG 2014
Date Deposited: 29 Oct 2015 03:16
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 50%
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030505 Physical Organic Chemistry @ 50%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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