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Remote Fluorination of α,β-Unsaturated Carbonyls via Silyl Dienol Ethers

journal contribution
posted on 2024-01-31, 23:03 authored by Daria Galaktionova, Sara Siddiqui, Justin MohrJustin Mohr
We report a general, regioselective, and metal free γ-fluorination of α,β-unsaturated carbonyls via silyl dienol ethers that are readily prepared from simple ketones and aldehydes. The transformation displays broad scope including 27 cyclic and acyclic siloxydienes providing γ-fluoro compounds in 28–91% yield. Notably, the reported conditions are also suitable for the synthesis of challenging tertiary fluorides. The regioselectivity of the reaction was studied on a series of acyclic siloxydienes and was observed to be sensitive to the conformational flexibility of the substrate. Diversification of the γ-fluorocarbonyls demonstrates the promise of fluorine as a stereocontrol element.

Funding

Methods for Regiocontrol in Polarized Polyene Systems | Funder: National Science Foundation | Grant ID: CHE-2154880

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Citation

Galaktionova, D., Siddiqui, S.Mohr, J. (2024). Remote Fluorination of α,β-Unsaturated Carbonyls via Silyl Dienol Ethers. ChemRxiv. https://doi.org/10.26434/chemrxiv-2024-rsh7w

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