The first visible-light-mediated synthesis of trifluoromethylselenolated arenes under metal-free conditions is reported. The use of an organic photocatalyst enables the trifluoromethylselenolation of arene diazonium salts using the shelf-stable reagent trifluoromethyl tolueneselenosulfonate at room temperature. The reaction does not require the presence of any additives and shows high functional-group tolerance, covering a very broad range of starting materials. Mechanistic investigations, including EPR spectroscopy, luminescence investigations, and cyclic voltammetry allow rationalization of the reaction mechanism.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/anie.201806165 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
-Trifluoromethylselenophthalimide, an Electrophilic Trifluoromethylselenolation Reagent and Its Application for the Synthesis of 4-Trifluoromethylselenolated Isoxazoles.
Org Lett
December 2023
School of Basic Medical Sciences, Xinxiang Medical University, Xinxiang, Henan 453003, China.
A new electrophilic trifluoromethylselenolation reagent, -trifluoromethylselenophthalimide (Phth-SeCF), was developed. A strategy for the synthesis of 4-trifluoromethylselenolated isoxazoles through electrophilic trifluoromethylselenolation cyclization has been established by using Phth-SeCF as an electrophilic reagent. Moreover, this protocol has the features of broad substrate scope, good functional group tolerance, and high yields.
View Article and Find Full Text PDFAromatic Trifluoromethylselenolation via Pd-catalyzed C-H functionalization.
Chemistry
September 2021
Institute of Chemistry and Biochemistry (ICBMS - UMR CNRS 5246), Univ Lyon, CNRS, Université Lyon 1, 43 Bd du 11 novembre 1918, 69622, Lyon, France.
The synthesis of trifluoromethylselenolated aromatic molecules via an auxiliary-assisted, palladium catalyzed, C-H bonds functionalization with trifluoromethyl tolueneselenosulfonate as reagent is described. The mono- or bis-products can be preferentially formed. Some mechanistic investigations were realized to better understand the reaction.
View Article and Find Full Text PDFMarkovnikov-Type Hydrotrifluoromethylchalcogenation of Unactivated Terminal Alkenes with [MeN][XCF] (X = S, Se) and TfOH.
Molecules
October 2020
School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan 430070, China.
The first Markovnikov-type hydrotrifluoromethylselenolation of unactivated terminal alkenes with the readily accessible [MeN][SeCF] reagent and the superacid TfOH is reported. The reaction proceeded at room temperature under catalyst- and additive-free conditions to give the branched trifluoromethylselenolated products in good yields. This protocol is also applicable to the Markovnikov-type hydrotrifluoromethylthiolation of unactivated terminal alkenes using [MeN][SCF]/TfOH, but not to the hydrotrifluoromethoxylation with CsOCF/TfOH under the same conditions.
View Article and Find Full Text PDFMetal-Free Alpha Trifluoromethylselenolation of Carbonyl Derivatives under Batch and Flow Conditions.
Molecules
February 2019
Dipartimento di Scienza e Alta Tecnologia, Università degli Studi Dell'Insubria, Via Valleggio 11, 22100 Como, Italy.
Trifluoromethylselenolated carbonyl compounds represent an emerging class with potential applications in several fields; however, a widespread use of such compound is hampered by the very limited number of strategies for their preparation. In this study we developed a method for the preparation of α-SeCF₃ substituted carbonyl derivatives using an in situ generated electrophilic ClSeCF₃ species. We also implemented an in-flow protocol to improve the safety features of the process.
View Article and Find Full Text PDFVisible-Light-Mediated Metal-Free Synthesis of Trifluoromethylselenolated Arenes.
Angew Chem Int Ed Engl
September 2018
Institute of Chemistry and Biochemistry (ICBMS-UMR, CNRS 5246), Univ Lyon, Université Lyon 1, CNRS, CPE-Lyon, INSA, 43 Bd du 11 Novembre 1918, 69622, Villeurbanne, France.
The first visible-light-mediated synthesis of trifluoromethylselenolated arenes under metal-free conditions is reported. The use of an organic photocatalyst enables the trifluoromethylselenolation of arene diazonium salts using the shelf-stable reagent trifluoromethyl tolueneselenosulfonate at room temperature. The reaction does not require the presence of any additives and shows high functional-group tolerance, covering a very broad range of starting materials.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!