A unique phenylboronic acid-catalyzed dimerization-sulfonylation of S-benzyl thiosulfonates has been disclosed. A metal-free tandem construction of S-S and C-S bonds is an operationally simple method to access a wide range of benzyl disulfanylsulfone derivatives in high to excellent yields. Moreover, the robustness of this tandem transformation has been demonstrated by gram-scale reactions, and a plausible mechanism is also proposed.
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http://dx.doi.org/10.1039/d0ob00442a | DOI Listing |
Org Biomol Chem
May 2020
X-ray Crystallography, CSIR-National Chemical Laboratory, Pune 411 008, India.
A unique phenylboronic acid-catalyzed dimerization-sulfonylation of S-benzyl thiosulfonates has been disclosed. A metal-free tandem construction of S-S and C-S bonds is an operationally simple method to access a wide range of benzyl disulfanylsulfone derivatives in high to excellent yields. Moreover, the robustness of this tandem transformation has been demonstrated by gram-scale reactions, and a plausible mechanism is also proposed.
View Article and Find Full Text PDFUltrason Sonochem
January 2020
Institute of Petrochemistry, Heilongjiang Academy of Sciences, Harbin 150040, China.
Layered double hydroxide (LDH)-supported Pd nanocatalysts (Pd/LDH-OH) were prepared by ultrasonic-assisted reduction at 30 °C using an ultrasonic bath at a frequency of 25 kHz and an input power of 400 W for 30 min without the addition of any stabilizing reagent or chemical reductant, using LDH with a layered structure and interparticle mesoporosity as the reductant and carrier. This kind of pore structure allows ultrasound waves to spread inside the pore and make ultrasound directly act on the surface hydroxyl groups of LDH, producing highly reductive free radicals (H). The reductive free radicals rapidly reduced Pd to Pd, forming ultrafine Pd nanoparticles (PdNPs) with a particle size distribution of 1.
View Article and Find Full Text PDFChem Commun (Camb)
May 2018
Graduate School of Engineering, Nagoya University, B2-3(611), Furo-cho, Chikusa, Nagoya 464-8603, Japan.
2,4-Bis(trifluoromethyl)phenylboronic acid is a highly effective catalyst for dehydrative amidation between carboxylic acids and amines. Mechanistic studies suggest that a 2 : 2 mixed anhydride is expected to be the only active species, and the ortho-substituent of boronic acid plays a key role in preventing the coordination of amines to the boron atom of the active species, thus accelerating the amidation. This catalyst works for α-dipeptide synthesis.
View Article and Find Full Text PDFAnalyst
May 2017
Department of Chemistry, Indiana University, 800 E. Kirkwood Avenue, Bloomington, Indiana 47405, USA.
A mobile nanofluidic device based on theta pipettes was developed for "collect-react-analyze" measurements of small volumes of a sample collected locally from biological samples. Specifically, we demonstrate execution of local reactions inside single cells and on Pseudomonas aeruginosa biofilms for targeted analysis of metabolites. Nanoliter volumes of the sample, post-reaction, were delivered to a mass spectrometer via electrospray ionization (ESI) for chemical analysis.
View Article and Find Full Text PDFUltrason Sonochem
January 2018
Chemical Engineering Department, Institute of Chemical Technology, Matunga, Mumbai 400 019, India. Electronic address:
Palladium-catalyzed Suzuki-Miyaura cross-coupling reaction is a significant reaction for obtaining industrially important products. The current research work deals with intensification of reaction of 4-bromoanisole and phenylboronic acid catalyzed with 5wt% Pd/C (5% by weight Pd supported on C available as commercial catalyst) using ultrasound and more importantly, without use of any additional phase transfer catalyst. Heterogeneous catalyst has been selected in the present work so as to harness the benefits of easy separation and the possible limitations of heterogeneous operation are minimized by introducing ultrasonic irradiations.
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