Decagram synthesis of dimethyl cubane dicarboxylate using continuous–flow photochemistry
Decagram synthesis of dimethyl cubane dicarboxylate using continuous–flow photochemistry
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% 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.
cubanes, continous-flow, photochemistry, photocycloaddition, upscaling
1307-1314
Collin, Diego Edgard
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Jackman, Edward Henry
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Jouandon, Nicolas
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Sun, Wei
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Light, Mark
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Harrowven, David C.
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Linclau, Bruno
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Collin, Diego Edgard
d0d4eecb-1e37-4bfe-ae07-351434d2f227
Jackman, Edward Henry
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Jouandon, Nicolas
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Sun, Wei
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Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Harrowven, David C.
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Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Collin, Diego Edgard, Jackman, Edward Henry, Jouandon, Nicolas, Sun, Wei, Light, Mark, Harrowven, David C. and Linclau, Bruno
(2020)
Decagram synthesis of dimethyl cubane dicarboxylate using continuous–flow photochemistry.
Synthesis, 53 (07), .
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% 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.
Text
Linclau_synthesis manuscript_revision v2
- Accepted Manuscript
Text
Synthesis_revised_accepted
- Accepted Manuscript
More information
Accepted/In Press date: 28 September 2020
e-pub ahead of print date: 4 November 2020
Keywords:
cubanes, continous-flow, photochemistry, photocycloaddition, upscaling
Identifiers
Local EPrints ID: 444735
URI: http://eprints.soton.ac.uk/id/eprint/444735
ISSN: 0039-7881
PURE UUID: 98c6188c-9e06-42c5-ab6b-770f8a2be3ef
Catalogue record
Date deposited: 02 Nov 2020 17:32
Last modified: 17 Mar 2024 05:58
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Contributors
Author:
Diego Edgard Collin
Author:
Edward Henry Jackman
Author:
Nicolas Jouandon
Author:
Wei Sun
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