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Literature DB >> 26418394

Silver-Mediated Oxidative Trifluoromethylation of Alcohols to Alkyl Trifluoromethyl Ethers.

Jian-Bo Liu¹, Xiu-Hua Xu¹, Feng-Ling Qing^1,2.

Abstract

The development of an efficient and practical method for the preparation of alkyl trifluoromethyl ethers is urgently demanding. The silver-mediated oxidative O-trifluoromethylation of primary, secondary, and tertiary alcohols with TMSCF3 under mild reaction conditions is established to provide a novel approach to a broad range of alkyl trifluoromethyl ethers. Further, this method is applied to the late-stage O-trifluoromethylation of complex natural products and prescribed pharmaceutical agents.

Entities: Chemical

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Year: 2015 PMID： 26418394 DOI： 10.1021/acs.orglett.5b02522

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

7 in total

1. Asymmetric silver-catalysed intermolecular bromotrifluoromethoxylation of alkenes with a new trifluoromethoxylation reagent.

Authors: Shuo Guo; Fei Cong; Rui Guo; Liang Wang; Pingping Tang
Journal: Nat Chem Date: 2017-01-23 Impact factor: 24.427

2. Trifluoromethyl Nonaflate: A Practical Trifluoromethoxylating Reagent and its Application to the Regio- and Stereoselective Synthesis of Trifluoromethoxylated Alkenes.

Authors: Zhichao Lu; Tatsuya Kumon; Gerald B Hammond; Teruo Umemoto
Journal: Angew Chem Int Ed Engl Date: 2021-06-17 Impact factor: 16.823

3. Dichlorotrifluoromethoxyacetic Acid: Preparation and Reactivity.

Authors: Riadh Zriba; Alaric Desmarchelier; Frédéric Cadoret; Sébastien Bouvet; Anne-Laure Barthelemy; Bruce Pégot; Patrick Diter; Guillaume Dagousset; Jean-Claude Blazejewski; Elsa Anselmi; Yurii Yagupolskii; Emmanuel Magnier
Journal: Molecules Date: 2017-06-09 Impact factor: 4.411

Silver-Mediated Oxidative Trifluoromethylation of Alcohols to Alkyl Trifluoromethyl Ethers.

1. Asymmetric silver-catalysed intermolecular bromotrifluoromethoxylation of alkenes with a new trifluoromethoxylation reagent.

2. Trifluoromethyl Nonaflate: A Practical Trifluoromethoxylating Reagent and its Application to the Regio- and Stereoselective Synthesis of Trifluoromethoxylated Alkenes.

3. Dichlorotrifluoromethoxyacetic Acid: Preparation and Reactivity.

4. Selective C-H trifluoromethoxylation of (hetero)arenes as limiting reagent.

5. Catalytic Stereoconvergent Synthesis of Homochiral β-CF₃, β-SCF₃, and β-OCF₃ Benzylic Alcohols.

6. 2'-O-Trifluoromethylated RNA - a powerful modification for RNA chemistry and NMR spectroscopy.

7. Rapid Dehydroxytrifluoromethoxylation of Alcohols.