Sulfonamides are prevalent functional groups represented in both natural and pharmaceutical products. The synthesis of sulfonamides is often straightforward when using nucleophilic amines and electrophilic sulfonyl chlorides. When reactivity challenges arise for nontraditional substrates, harsh conditions or new synthetic routes may be required. Here we report a method using silyl triflate additives to overcome reactivity limitations when electron deficient and sterically encumbered amines are used in conjunction with electron rich or bulky sulfonyl chlorides.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.5c00011 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Silyl Triflate-Promoted Sulfonylations.
Org Lett
January 2025
Pfizer Oncology Medicinal Chemistry, San Diego, California 92121, United States.
Sulfonamides are prevalent functional groups represented in both natural and pharmaceutical products. The synthesis of sulfonamides is often straightforward when using nucleophilic amines and electrophilic sulfonyl chlorides. When reactivity challenges arise for nontraditional substrates, harsh conditions or new synthetic routes may be required.
View Article and Find Full Text PDFA sulfonated and nitrated polyether ether ketone/polyvinyl chloride modified atmosphere packaging delays the deterioration of grapes.
J Sci Food Agric
January 2025
College of Food Science and Engineering, South China University of Technology, Guangzhou, China.
Background: Polyether ether ketone (PEEK) was modified by a sulfuric and nitric acid mixed system to improve the solubility of the material and the gas selective permeability of the film. SN1 and SN5, synthesized from mixed acid systems (with ratios of nitric acid and sulfuric acid of 1:1 and 1:5, respectively) were chosen because they had comparable nitro groups but differing sulfonyl groups. To investigate the impact of the type and content of sulfonated and nitrated polyether ether ketone (SNPEEK) on the structure and physicochemical properties of the films, SN1/polyvinyl chloride (PVC) and SN5/polyvinyl chloride films were made by adding varying amounts of SN1 and SN5 (0.
View Article and Find Full Text PDFThe Synthesis, Crystal Structure, Modification, and Cytotoxic Activity of α-Hydroxy-Alkylphosphonates.
Molecules
January 2025
Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., 1111 Budapest, Hungary.
A series of α-hydroxy-alkylphosphonates and α-hydroxy-alkylphosphine oxides were synthesized by the Pudovik reaction of acetaldehyde and acetone with dialkyl phosphites or diarylphosphine oxides. The additions were performed in three different ways: in liquid phase using triethylamine as the catalyst (1), on the surface of AlO/KF solid catalyst (2), or by a MW-assisted NaCO-catalyzed procedure (3). In most of the cases, our methods were more efficient and more robust than those applied in the literature.
View Article and Find Full Text PDFSolvatochromism and cis-trans isomerism in azobenzene-4-sulfonyl chloride.
Photochem Photobiol Sci
January 2025
CQC-IMS, Department of Chemistry, University of Coimbra, 3004-535, Coimbra, Portugal.
Solvatochromism exhibited by azobenzene-4-sulfonyl chloride (here abbreviated as Azo-SCl) has been investigated in a series of non-polar, polar-aprotic and polar-protic solvents. The UV-vis spectra of Azo-SCl exhibit two long-wavelength bands, observed at 321-330 nm (band-I) and 435-461 nm (band-II), which are ascribed to the π*-π (S ← S) and π*-n (S ← S) transitions, respectively. The shorter wavelength band indicates a reversal in solvatochromism, from negative to positive solvatochromism, for a solvent with a dielectric constant of 32.
View Article and Find Full Text PDFRecent progress in C-S bond formation electron donor-acceptor photoactivation.
Org Biomol Chem
January 2025
Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, Nanjing Forestry University, Nanjing 210037, China.
Recent advancements in C-S bond formation electron donor-acceptor (EDA) complex photoactivation have been remarkable. EDA complexes, which are composed of electron donors and acceptors, facilitate C-S bond construction under mild conditions through single-electron transfer events upon visible light irradiation. This review highlights the utilization of various sulfur-containing substrates, including diacetoxybenzenesulfonyl (DABSO), sulfonic acids, sodium sulfinates, sulfonyl chlorides, and thiophenols, in EDA-promoted sulfonylation and thiolation reactions, covering the works published since 2017 to date.
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!