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Decagram synthesis of dimethyl cubane dicarboxylate using continuous–flow photochemistry

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
0039-7881
Collin, Diego Edgard
d0d4eecb-1e37-4bfe-ae07-351434d2f227
Jackman, Edward Henry
cb6d380d-8128-4786-906b-4f4de74eea68
Jouandon, Nicolas
7df85b49-eec3-40bd-a69e-5b28c2ecac68
Sun, Wei
bca29e03-90fc-4684-875e-61d35f1b5cba
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Collin, Diego Edgard
d0d4eecb-1e37-4bfe-ae07-351434d2f227
Jackman, Edward Henry
cb6d380d-8128-4786-906b-4f4de74eea68
Jouandon, Nicolas
7df85b49-eec3-40bd-a69e-5b28c2ecac68
Sun, Wei
bca29e03-90fc-4684-875e-61d35f1b5cba
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
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. (In Press)

Record type: Article

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
Restricted to Repository staff only until 28 September 2021.
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Text
Synthesis_revised_accepted - Accepted Manuscript
Restricted to Repository staff only until 28 September 2021.
Request a copy

More information

Accepted/In Press date: 28 September 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
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

Catalogue record

Date deposited: 02 Nov 2020 17:32
Last modified: 18 Feb 2021 16:55

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