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

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.

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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

Published date: 2 July 2021

Additional Information: Funding Information: The authors acknowledge financial support from the ERDF (LabFact: InterReg V project 121) and EPSRC (core capability EP/K039466/1). K.K. thanks NZP for funding and is grateful for a Denis Henry Desty PhD Scholarship. Publisher Copyright: ©

Keywords: amides, anions, irradiation, organic compounds, reaction products

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