Photoinduced Proton‐Transfer Reactions for Mild O‐H Functionalization of Unreactive Alcohols †
Abstract: Hexafluoroisopropanol is typically considered as an unreactive solvent and not as a reagent in organic synthesis. Herein, we report on a mild and efficient photochemical reaction of aryl diazoacetates with hexafluoroisopropanol that enables, under stoichiometric reaction conditions, the synthesis of fluorinated ethers in excellent yield. Mechanistic studies indicate there is a preorganization of hexafluoroisopropanol and the diazoalkane acts as an unreactive hydrogen‐bonding complex. Only after photoexcitation does this complex undergo a protonation‐substitution reaction to the reaction product. Investigations on the applicability of this photochemical transformation show that a broad variety of acidic alcohols can be subjected to this transformation and thus demonstrate the feasibility of this concept for O‐H functionalization reactions (54 examples, up to 98 % yield).
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Photoinduced Proton‐Transfer Reactions for Mild O‐H Functionalization of Unreactive Alcohols † ; volume:59 ; number:14 ; year:2020 ; pages:5562-5566 ; extent:5
Angewandte Chemie / International edition. International edition ; 59, Heft 14 (2020), 5562-5566 (gesamt 5)
- Creator
- DOI
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10.1002/anie.201915161
- URN
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urn:nbn:de:101:1-2022061113045768428346
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:28 AM CEST
Data provider
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Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Jana, Sripati
- Yang, Zhen
- Li, Fang
- Empel, Claire
- Ho, Junming
- Koenigs, Rene M.
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