Decagram Synthesis of Dimethyl 1,4-Cubanedicarboxylate Using Continuous-Flow Photochemistry

Diego E. Collin; Edward H. Jackman; Nicolas Jouandon; Wei Sun; Mark E. Light; David C. Harrowven; Bruno Linclau

doi:10.1055/s-0040-1705964

Synthesis, Table of Contents

Synthesis 2021; 53(07): 1307-1314
DOI: 10.1055/s-0040-1705964

paper

Decagram Synthesis of Dimethyl 1,4-Cubanedicarboxylate Using Continuous-Flow Photochemistry

Diego E. Collin

,

Edward H. Jackman

,

Nicolas Jouandon

,

Wei Sun

,

Mark E. Light

,

David C. Harrowven

,

Bruno Linclau∗

School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK Email: bruno.linclau@soton.ac.uk

› Author Affiliations

Abstract

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Abstract

The highly strained cubane system is of great interest as a scaffold and rigid linker in both pharmaceutical and materials chemistry. A straightforward approach is reported for the scale-up of a [2+2] photocycloaddition step using convenient home-made flow photoreactors to access dimethyl 1,4-cubanedicarboxylate on decagram-scale in 33–40% yield over 8 steps. The process is demonstrated on 3.4 g·h^–1 input with 30 minutes residence time, enabling to reduce the process time and to avoid the use of batch photoreactors. Completion of the characterisation of the photocycloadduct and its hydrates is reported.

Key words

cubanes - continuous-flow - photochemistry - photocycloaddition - upscaling

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References

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