Langlois’ reagent (trifluoromethanesulfinate salt) has been proven to be a valuable reagent for the synthesis of various classes of molecules, mainly trifluoromethylated compounds, in academic, biological and industrial research. Synthetic uses of Langlois’ reagent in organic transformations of aromatic and heteroaromatic compounds, alkenes, alkynes, boronic acids, carboxylic acids, and etc are discussed.This review aims to demonstrate the ongoing utility of Langlois’ reagent in the preparation of various classes of organic compounds. Furthermore, to address the recent collective papers, the current review summarizes and comprehensively describes manuscripts on synthetic applications of Langlois’ reagent since 2015 until today.
In situ generated gold nanoparticles inside the
nanospaces of periodic mesoporous organosilica with an imidazolium
framework (Au@PMO-IL) were found to be highly active, selective, and
reusable catalysts for the aerobic oxidation of activated and nonactivated
alcohols under mild reaction conditions. The catalyst was characterized
by nitrogen adsorption–desorption measurement, thermogravimetric
analysis (TGA), transmission electron microscopy (TEM), elemental
analysis (EA), diffuse reflectance infrared Fourier transform spectroscopy
(DRIFT), X-ray photoelectron spectroscopy (XPS), and inductively coupled
plasma atomic emission spectroscopy (ICP-AES). The catalyst exhibited
excellent catalytic activity in the presence of either Cs2CO3 (35 °C) or K2CO3 (60 °C)
as reaction bases in toluene as a reaction solvent. Under both reaction
conditions, various types of alcohols (up to 35 examples) including
activated benzylic, primary and secondary aliphatic, heterocyclic,
and challenging cyclic aliphatic alcohols converted to the expected
carbonyl compounds in good to excellent yields and selectivity. The
catalyst was also recovered and reused for at least seven reaction
cycles. Data from three independent leaching tests indicated that
amounts of leached gold particles were negligible (<0.2 ppm). It
is believed that the combination of bridged imidazolium groups and
confined nanospaces of PMO-IL might be a major reason explaining the
remarkable stabilization and homogeneous distribution of in situ generated
gold nanoparticles, thus resulting in the highly active and recyclable
catalyst system.
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