Selective, Transition Metal-free 1,2-Diboration of Alkyl Halides, Tosylates, and Alcohols
Zitieren Sie bitte immer diese URN: urn:nbn:de:bvb:20-opus-318262
- Defunctionalization of readily available feedstocks to provide alkenes for the synthesis of multifunctional molecules represents an extremely useful process in organic synthesis. Herein, we describe a transition metal-free, simple and efficient strategy to access alkyl 1,2-bis(boronate esters) via regio- and diastereoselective diboration of secondary and tertiary alkyl halides (Br, Cl, I), tosylates, and alcohols. Control experiments demonstrated that the key to this high reactivity and selectivity is the addition of a combination of potassiumDefunctionalization of readily available feedstocks to provide alkenes for the synthesis of multifunctional molecules represents an extremely useful process in organic synthesis. Herein, we describe a transition metal-free, simple and efficient strategy to access alkyl 1,2-bis(boronate esters) via regio- and diastereoselective diboration of secondary and tertiary alkyl halides (Br, Cl, I), tosylates, and alcohols. Control experiments demonstrated that the key to this high reactivity and selectivity is the addition of a combination of potassium iodide and N,N-dimethylacetamide (DMA). The practicality and industrial potential of this transformation are demonstrated by its operational simplicity, wide functional group tolerance, and the late-stage modification of complex molecules. From a drug discovery perspective, this synthetic method offers control of the position of diversification and diastereoselectivity in complex ring scaffolds, which would be especially useful in a lead optimization program.…
Autor(en): | Mingming Huang, Jiefeng Hu, Shasha Shi, Alexandra Friedrich, Johannes Krebs, Stephen A. Westcott, Udo Radius, Todd B. Marder |
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URN: | urn:nbn:de:bvb:20-opus-318262 |
Dokumentart: | Artikel / Aufsatz in einer Zeitschrift |
Institute der Universität: | Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie |
Sprache der Veröffentlichung: | Englisch |
Titel des übergeordneten Werkes / der Zeitschrift (Englisch): | Chemistry-A European Journal |
Erscheinungsjahr: | 2022 |
Band / Jahrgang: | 28 |
Heft / Ausgabe: | 24 |
Aufsatznummer: | e202200480 |
Originalveröffentlichung / Quelle: | Chemistry-A European Journal 2022, 28(24):e202200480. DOI: 10.1002/chem.202200480 |
DOI: | https://doi.org/10.1002/chem.202200480 |
Allgemeine fachliche Zuordnung (DDC-Klassifikation): | 5 Naturwissenschaften und Mathematik / 54 Chemie / 546 Anorganische Chemie |
Freie Schlagwort(e): | alkyl halides; boronate esters; organic synthesis |
Datum der Freischaltung: | 04.07.2023 |
Lizenz (Deutsch): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |