Synthesis of ortho-functionalized 1,4-cubanedicarboxylate derivatives through photochemical chlorocarbonylation
- Author
- Diego E. Collin, Kristina Kovacic, Mark E. Light and Bruno Linclau (UGent)
- Organization
- 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.
- Keywords
- REDOX-ACTIVE ESTERS, C-H BONDS, SYSTEMATIC SUBSTITUTION, OXALYL, CHLORIDE, CUBANE NUCLEUS, CARBOXYLATION, CHEMISTRY, ACTIVATION, LIBRARIES, ROUTE
Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-01GM8FYB4T8TG1WRV577T50APR
- MLA
- Collin, Diego E., et al. “Synthesis of Ortho-Functionalized 1,4-Cubanedicarboxylate Derivatives through Photochemical Chlorocarbonylation.” ORGANIC LETTERS, vol. 23, no. 13, 2021, pp. 5164–69, doi:10.1021/acs.orglett.1c01702.
- APA
- Collin, D. E., Kovacic, K., Light, M. E., & Linclau, B. (2021). Synthesis of ortho-functionalized 1,4-cubanedicarboxylate derivatives through photochemical chlorocarbonylation. ORGANIC LETTERS, 23(13), 5164–5169. https://doi.org/10.1021/acs.orglett.1c01702
- Chicago author-date
- Collin, Diego E., Kristina Kovacic, Mark E. Light, and Bruno Linclau. 2021. “Synthesis of Ortho-Functionalized 1,4-Cubanedicarboxylate Derivatives through Photochemical Chlorocarbonylation.” ORGANIC LETTERS 23 (13): 5164–69. https://doi.org/10.1021/acs.orglett.1c01702.
- Chicago author-date (all authors)
- Collin, Diego E., Kristina Kovacic, Mark E. Light, and Bruno Linclau. 2021. “Synthesis of Ortho-Functionalized 1,4-Cubanedicarboxylate Derivatives through Photochemical Chlorocarbonylation.” ORGANIC LETTERS 23 (13): 5164–5169. doi:10.1021/acs.orglett.1c01702.
- Vancouver
- 1.Collin DE, Kovacic K, Light ME, Linclau B. Synthesis of ortho-functionalized 1,4-cubanedicarboxylate derivatives through photochemical chlorocarbonylation. ORGANIC LETTERS. 2021;23(13):5164–9.
- IEEE
- [1]D. E. Collin, K. Kovacic, M. E. Light, and B. Linclau, “Synthesis of ortho-functionalized 1,4-cubanedicarboxylate derivatives through photochemical chlorocarbonylation,” ORGANIC LETTERS, vol. 23, no. 13, pp. 5164–5169, 2021.
@article{01GM8FYB4T8TG1WRV577T50APR,
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.}},
author = {{Collin, Diego E. and Kovacic, Kristina and Light, Mark E. and Linclau, Bruno}},
issn = {{1523-7060}},
journal = {{ORGANIC LETTERS}},
keywords = {{REDOX-ACTIVE ESTERS,C-H BONDS,SYSTEMATIC SUBSTITUTION,OXALYL,CHLORIDE,CUBANE NUCLEUS,CARBOXYLATION,CHEMISTRY,ACTIVATION,LIBRARIES,ROUTE}},
language = {{eng}},
number = {{13}},
pages = {{5164--5169}},
title = {{Synthesis of ortho-functionalized 1,4-cubanedicarboxylate derivatives through photochemical chlorocarbonylation}},
url = {{http://doi.org/10.1021/acs.orglett.1c01702}},
volume = {{23}},
year = {{2021}},
}
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