Yuwen Zeng

Silver-mediated trifluoromethylation-iodination of arynes.

An unprecedented silver-mediated vicinal trifluoromethylation-iodination of arynes that quickly introduces CF(3) and I groups onto aromatic rings in a single step to give o-trifluoromethyl iodoarenes has been developed. A new reactivity of AgCF(3) has been revealed, and 2,2,6,6-tetramethylpiperidine plays an important role in this difunctionalization reaction.An unprecedented silver-mediated vicinal trifluoromethylation-iodination of arynes that quickly introduces CF3 and I groups onto aromatic rings in a single step to give o-trifluoromethyl iodoarenes has been developed. A new reactivity of AgCF3 has been re

Recent Advances in the One-Step Synthesis of Distally Fluorinated Ketones

Fluorinated ketones are intriguing compounds in synthetic chemistry and life science-related fields. The development of efficient methodologies to obtain these compounds is of significant importance and has therefore attracted considerable attention. This Minireview highlights recent progress made in the synthesis of fluorine-containing ketones, with an emphasis on those methods in which the construction of carbonyl groups is synergetic with distal (β-, γ-, δ-, etc.) incorporation of fluorine atoms or fluorinated groups.

Silver‐Catalyzed Formal Insertion of Arynes into RfI Bonds

An unprecedented silver-catalyzed formal insertion of arynes into Rf-I (Rf = CF3, C2F5) bonds has been developed. This protocol provides easy access to various ortho-perfluoroalkyl iodoarenes under mild conditions. In this insertion reaction, an ionic atom-transfer reaction of RfI occurs, and a silver-mediated metathesis process is involved in the efficient transfer of the electropositive iodine atom.

Diphenyliodonium‐Catalyzed Fluorination of Arynes: Synthesis of ortho‐Fluoroiodoarenes

Described is a one-pot vicinal fluorination-iodination of arynes at room temperature. The diphenyliodonium salt proved to be a privileged catalyst for this nucleophilic fluorination process using CsF as a fluorine source, and a subsequent facile electrophilic iodination with C4 F9 I was also found to be crucial to ensure the efficient fluorination. This new synthetic protocol has a broad substrate scope under mild reaction conditions.

Silver-Mediated Trifluoromethylthiolation-Iodination of Arynes.

A one-pot trifluoromethylthiolation-iodination of arynes with trifluoromethylthiosilver (AgSCF3) and 1-iodophenylacetylene is described. This protocol allows rapid construction of o-trifluoromethylthiolated arene building blocks in moderate yields. These products were found to be excellent precursors for Yagupolskii-Umemoto-type electrophilic trifluoromethylation reagents.

Trifluoromethyl Benzoate: A Versatile Trifluoromethoxylation Reagent

Trifluoromethyl benzoate (TFBz) is developed as a new shelf-stable trifluoromethoxylation reagent, which can be easily prepared from inexpensive starting materials using KF as the only fluorine source. The synthetic potency of TFBz is demonstrated by trifluoromethoxylation-halogenation of arynes, nucleophilic substitution of alkyl (pseudo)halides, cross-coupling with aryl stannanes, and asymmetric difunctionalization of alkenes. The unprecedented trifluoromethoxylation-halogenation of arynes proceeds smoothly at room temperature with the aid of a crown ether-complexed potassium cation, which significantly stabilizes the trifluoromethoxide anion derived from TFBz.

Recent advances in green fluorine chemistry

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