Conformational Flexibility as a Tool for Enabling Site-Selective Functionalization of Unactivated sp 3 C–O Bonds in Cyclic Acetals
| Autor: | Laura Talavera, Ruben Martin, Enrique Gomez Bengoa, Ciro Romano |
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| Přispěvatelé: | European Commission |
| Jazyk: | angličtina |
| Předmět: | |
| Zdroj: | Addi. Archivo Digital para la Docencia y la Investigación instname |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/jacs.2c04513 |
| Popis: | A dual catalytic manifold that enables site-selective functionalization of unactivated sp(3) C-O bonds in cyclic acetals with aryl and alkyl halides is reported. The reaction is triggered by an appropriate sigma*-p orbital overlap prior to sp(3) C-O cleavage, thus highlighting the importance of conformational flexibility in both reactivity and site selectivity. The protocol is characterized by its excellent chemoselectivity profile, thus offering new vistas for activating strong sigma sp(3) C-O linkages. We thank ICIQ, FEDER/MCI-AEI/PGC2018-096839-B-I00, MCIN-PID2019-110008GB-I00, European Research Council (ERC) under European Union's Horizon 2020 research and innovation program (Grant Agreement No. 883756) for financial support. E.G.-B. thanks SGIker (UPV/EHU) for providing human and computational resources. C.R. thanks the European Union's Horizon 2020 and innovation program under the Marie Sklodowska-Curie grant agreement (839980). |
| Databáze: | OpenAIRE |
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