AI Article Synopsis

Article Abstract

In this report, we have established a novel and efficient method for selectively synthesizing either vinyl sulfides or 2-methylbenzothiazoles from the reaction of CaC and disulfides. The selective synthesis of these two distinct products can be controlled by simply adjusting the amount of KS. The underlying reaction mechanism has been thoroughly investigated through control experiments, HRMS, and FTIR, which collectively support the pivotal role of a trisulfur radical anion. This radical species, generated in situ from KS, is essential for the homolytic cleavage of the S-S bonds in a catalytic manner. Additionally, the trisulfur radical anion also acts as an effective mediator for activating the vinyl group of 2-aminophenyl vinyl sulfides, facilitating the crucial intramolecular cyclization required to produce 2-methylbenzothiazoles. Moreover, CaC not only serves as an acetylene source but also creates the basic conditions essential for the selective formation of vinyl sulfides. This methodology demonstrates broad substrate compatibility and excellent functional group tolerance, significantly enhancing its practical utility in diverse synthetic applications.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.4c01664DOI Listing

Publication Analysis

Top Keywords

vinyl sulfides
16
trisulfur radical
12
radical anion
12
selective synthesis
8
vinyl
5
synthesis vinyl
4
sulfides
4
sulfides 2-methyl
4
2-methyl benzothiazoles
4
benzothiazoles disulfides
4

Similar Publications

Isotopic labeling is a powerful technique extensively used in the pharmaceutical industry. By tracking isotope-labeled molecules, researchers gain unique and invaluable insights into the pharmacokinetics and pharmacodynamics of new drug candidates. Hydrogen isotope labeling is particularly important as hydrogen is ubiquitous in organic molecules in biological systems, and it can be introduced effectively through late-stage hydrogen isotope exchange (HIE).

View Article and Find Full Text PDF

Thanatin is a β-hairpin antimicrobial peptide cyclised by a single disulfide bond that has shown potent broad-spectrum activity towards bacterial and fungal pathogens. Towards Gram-negative species, thanatin acts both by forming trans-membranal pores and inhibiting outer membrane biogenesis by binding to LptA and blocking lipopolysaccharide (LPS) transport. Inspired by previous modifications of thanatin, an analogue was prepared which demonstrated potent but selective activity towards .

View Article and Find Full Text PDF

Phase-Transition-Promoted Interfacial Anchoring of Sulfide Solid Electrolyte Membranes for High-Performance All-Solid-State Lithium Battery.

Adv Sci (Weinh)

November 2024

State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai, 201620, P. R. China.

Solvent-free manufacturing is crucial for fabricating high-performance sulfide-electrolyte-based all-solid-state lithium batteries (ASSLBs), with advantages including side reaction inhibition, less contamination, and practical scalability. However, the fabricated sulfide electrolytes commonly suffer from brittleness, limited ion transport, and unsatisfactory interfacial stability due to the uncontrolled dispersion of the sulfide particles within the polymer binder matrix. Herein, a "solid-to-liquid" phase transition strategy is reported to fabricate flexible LiPSCl (LPSCl) electrolytes.

View Article and Find Full Text PDF

Biocatalysis has been widely employed for the generation of carbon-carbon/heteroatom stereocentres, yet its application in chiral C(sp)-S bond construction is rare and limited to enzymatic kinetic resolutions. Herein, we describe the enantioselective construction of chiral C(sp)-S bonds through ene-reductase biocatalyzed conjugate reduction of prochiral vinyl sulfides. A series of cooperative sequential/concurrent chemoenzymatic and biocatalytic cascades have been developed to access a broad range of chiral sulfides, including valuable β-hydroxysulfides bearing two adjacent C(sp)-S and C(sp)-O stereocentres, in a stereoconvergent manner with good to excellent yields (up to 96%) and enantioselectivities (up to >99% ee).

View Article and Find Full Text PDF

Want 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!