Selective, Transition Metal-free 1,2-Diboration of Alkyl Halides, Tosylates, and Alcohols
Please always quote using this 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.…
Author: | 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 |
Document Type: | Journal article |
Faculties: | Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie |
Language: | English |
Parent Title (English): | Chemistry-A European Journal |
Year of Completion: | 2022 |
Volume: | 28 |
Issue: | 24 |
Article Number: | e202200480 |
Source: | Chemistry-A European Journal 2022, 28(24):e202200480. DOI: 10.1002/chem.202200480 |
DOI: | https://doi.org/10.1002/chem.202200480 |
Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 546 Anorganische Chemie |
Tag: | alkyl halides; boronate esters; organic synthesis |
Release Date: | 2023/07/04 |
Licence (German): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |