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Synthesis of ortho-functionalized 1,4-cubanedicarboxylate derivatives through photochemical chlorocarbonylation

Synthesis of ortho-functionalized 1,4-cubanedicarboxylate derivatives through photochemical chlorocarbonylation
Synthesis of ortho-functionalized 1,4-cubanedicarboxylate derivatives through photochemical chlorocarbonylation
The cubane ring has received intense attention as a 3D benzene isostere and scaffold. Mono- and 1,4-disubstituted cubanes are well-described. Here we report a practical procedure for a direct radical-mediated chlorocarbonylation process initially reported by Bashir-Hashemi, to access a range of 2-substituted 1,4-cubanedicarboxylic ester derivatives. A subsequent regioselective ester hydrolysis to give fully differentiated 1,2,4-trisubstituted cubanes is demonstrated.
amides, anions, irradiation, organic compounds, reaction products
1523-7060
5164-5169
Collin, Diego, Edgard
d0d4eecb-1e37-4bfe-ae07-351434d2f227
Kovacic, Kristina
341dad39-1119-43de-8d1d-6c071f88da65
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Collin, Diego, Edgard
d0d4eecb-1e37-4bfe-ae07-351434d2f227
Kovacic, Kristina
341dad39-1119-43de-8d1d-6c071f88da65
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba

Collin, Diego, Edgard, Kovacic, Kristina, Light, Mark and Linclau, Bruno (2021) Synthesis of ortho-functionalized 1,4-cubanedicarboxylate derivatives through photochemical chlorocarbonylation. Organic Letters, 23 (13), 5164-5169. (doi:10.1021/acs.orglett.1c01702).

Record type: Article

Abstract

The cubane ring has received intense attention as a 3D benzene isostere and scaffold. Mono- and 1,4-disubstituted cubanes are well-described. Here we report a practical procedure for a direct radical-mediated chlorocarbonylation process initially reported by Bashir-Hashemi, to access a range of 2-substituted 1,4-cubanedicarboxylic ester derivatives. A subsequent regioselective ester hydrolysis to give fully differentiated 1,2,4-trisubstituted cubanes is demonstrated.

Text
1,2,4-Cubanes_revised v3accb - Accepted Manuscript
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Accepted/In Press date: 11 June 2021
e-pub ahead of print date: 16 June 2021
Keywords: amides, anions, irradiation, organic compounds, reaction products

Identifiers

Local EPrints ID: 450074
URI: http://eprints.soton.ac.uk/id/eprint/450074
ISSN: 1523-7060
PURE UUID: 383b6fbb-2d6c-4214-868f-95ecd8351da5
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

Catalogue record

Date deposited: 08 Jul 2021 16:31
Last modified: 26 Nov 2021 02:43

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Contributors

Author: Diego, Edgard Collin
Author: Kristina Kovacic
Author: Mark Light ORCID iD
Author: Bruno Linclau ORCID iD

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