From propenolysis to enyne metathesis: tools for expedited assembly of 4 a ,8 a -azaboranaphthalene and extended polycycles with embedded BN.
| Autor: | Rulli F; BISi-Bonds/CRISOL Group, Dept. of Organic and Pharmaceutical Chemistry. Institut Químic de Sarrià, Universitat Ramon Llull Vía Augusta 390 08017 Barcelona Spain anabelen.cuenca@iqs.url.edu., Sanz-Liarte G; BISi-Bonds Group, Dept. Química Biológica. Institut de Química Avançada de Catalunya, IQAC-CSIC C/Jordi Girona 20 08034 Barcelona Spain alexandr.shafir@iqac.csic.es., Roca P; BISi-Bonds Group, Dept. Química Biológica. Institut de Química Avançada de Catalunya, IQAC-CSIC C/Jordi Girona 20 08034 Barcelona Spain alexandr.shafir@iqac.csic.es., Martínez N; BISi-Bonds/CRISOL Group, Dept. of Organic and Pharmaceutical Chemistry. Institut Químic de Sarrià, Universitat Ramon Llull Vía Augusta 390 08017 Barcelona Spain anabelen.cuenca@iqs.url.edu., Medina V; BISi-Bonds Group, Dept. Química Biológica. Institut de Química Avançada de Catalunya, IQAC-CSIC C/Jordi Girona 20 08034 Barcelona Spain alexandr.shafir@iqac.csic.es., Puig de la Bellacasa R; BISi-Bonds/CRISOL Group, Dept. of Organic and Pharmaceutical Chemistry. Institut Químic de Sarrià, Universitat Ramon Llull Vía Augusta 390 08017 Barcelona Spain anabelen.cuenca@iqs.url.edu., Shafir A; BISi-Bonds Group, Dept. Química Biológica. Institut de Química Avançada de Catalunya, IQAC-CSIC C/Jordi Girona 20 08034 Barcelona Spain alexandr.shafir@iqac.csic.es.; Centro de Innovación en Química Avanzada (ORFEO-CINQA) Barcelona Spain., Cuenca AB; BISi-Bonds/CRISOL Group, Dept. of Organic and Pharmaceutical Chemistry. Institut Químic de Sarrià, Universitat Ramon Llull Vía Augusta 390 08017 Barcelona Spain anabelen.cuenca@iqs.url.edu.; Centro de Innovación en Química Avanzada (ORFEO-CINQA) Barcelona Spain. |
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| Jazyk: | angličtina |
| Zdroj: | Chemical science [Chem Sci] 2024 Mar 07; Vol. 15 (15), pp. 5674-5680. Date of Electronic Publication: 2024 Mar 07 (Print Publication: 2024). |
| DOI: | 10.1039/d3sc06676b |
| Abstrakt: | The synthesis of BN-containing molecules, which have an interesting isosteric relationship to their parent all-C cores, has drawn a great deal of attention as an avenue to alter and tune molecular function. Nevertheless, many cores with embedded BN are still hard to synthesize, and thus, further effort is required in this direction. Herein, we present an integrated approach to BN-containing polycycles rooted in an exceptionally clean B-N condensation of amines with a tri-allylborane. Having released propene as the only byproduct, the resulting BN precursors are seamlessly telescoped into BN-containing polycyclic cores via a set of additional methodologies, either developed here ad-hoc or applied for the first time for the synthesis of BN-cycles. As the "sharpening stone" of the process, BN-embedded naphthalene, which has previously only been obtained in low yield, can now be synthesized efficiently through propenolysis, ring-closing metathesis and a new high-yielding aromatization. As a more advanced application, an analogously obtained BN-containing bis-enyne is readily converted to BN-containing non-aromatic tetra-, penta- and hexacyclic structures via ring-closing enyne metathesis, followed by the Diels-Alder cycloaddition. The resulting air-sensitive structures are easily handled by preventive hydration (quaternization) of their B-N bridge; reverting this hydration restores the original B Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.) |
| Databáze: | MEDLINE |
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