دورية أكاديمية
Modular synthesis of complex benzoxaboraheterocycles through chelation-assisted Rh-catalyzed [2+2+2] cycloaddition
| العنوان: | Modular synthesis of complex benzoxaboraheterocycles through chelation-assisted Rh-catalyzed [2+2+2] cycloaddition |
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| المؤلفون: | Halford-McGuff, John, Varga, Marek, Cordes, David B., McKay, Aidan, Watson, Allan J. B. |
| المساهمون: | UK Research and Innovation, The Leverhulme Trust, University of St Andrews. School of Chemistry, University of St Andrews. EaSTCHEM, University of St Andrews. Sir James Mackenzie Institute for Early Diagnosis |
| سنة النشر: | 2024 |
| المجموعة: | University of St Andrews: Digital Research Repository |
| مصطلحات موضوعية: | Boron, Cycloaddition, Heterocycles, Mechanism, Sensing, QD Chemistry, DAS, MCC, QD |
| الوصف: | Funding: J.M.H.-M. and M.V. thank the EaSI-CAT Centre for Doctoral Training for PhD studentships. A.J.B.W. thanks the Leverhulme Trust for a research fellowship (RF-2022-014) and the EPSRC Programme Grant “Boron: Beyond the Reagent” (EP/W007517/1) for support. ; Benzoxaboraheterocycles (BOBs) are moieties of increasing interest in the pharmaceutical industry; however, the synthesis of these compounds is often difficult or impractical due to the sensitivity of the boron moiety, the requirement for metalation–borylation protocols, and lengthy syntheses. We report a straightforward, modular approach that enables access to complex examples of the BOB framework through a Rh-catalyzed [2 + 2 + 2] cycloaddition using MIDA-protected alkyne boronic acids. The key to the development of this methodology was overcoming the steric barrier to catalysis by leveraging chelation assistance. We show the utility of the method through synthesis of a broad range of BOB scaffolds, mechanistic information on the chelation effect, intramolecular alcohol-assisted BMIDA hydrolysis, and linear/cyclic BOB limits as well as comparative binding affinities of the product BOB frameworks for ribose-derived biomolecules. ; Peer reviewed |
| نوع الوثيقة: | article in journal/newspaper |
| وصف الملف: | application/pdf |
| اللغة: | English |
| تدمد: | 2155-5435 |
| العلاقة: | ACS Catalysis; 298078755; b609a452-ec7a-4301-a9b3-a317f72cb990; 85184590171; Halford-McGuff , J , Varga , M , Cordes , D B , McKay , A & Watson , A J B 2024 , ' Modular synthesis of complex benzoxaboraheterocycles through chelation-assisted Rh-catalyzed [2+2+2] cycloaddition ' , ACS Catalysis , vol. 14 , no. 3 , pp. 1846-1854 . https://doi.org/10.1021/acscatal.3c05766Test; ORCID: /0000-0002-5366-9168/work/152899217; ORCID: /0000-0002-1582-4286/work/152899564; https://hdl.handle.net/10023/29153Test; EP/W007517/1; RF-2022-014 |
| DOI: | 10.1021/acscatal.3c05766 |
| الإتاحة: | https://doi.org/10.1021/acscatal.3c05766Test https://hdl.handle.net/10023/29153Test |
| رقم الانضمام: | edsbas.8E9535E3 |
| قاعدة البيانات: | BASE |
| تدمد: | 21555435 |
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| DOI: | 10.1021/acscatal.3c05766 |