The synthetic potential of KI as the iodide source in aryne three-component coupling has been demonstrated using aldehydes as the third component. This mild and transition-metal-free coupling reaction allowed the straightforward synthesis of 2-iodobenzyl alcohols in moderate to good yields with good functional group compatibility. Moreover, KBr and KCl could be used as the nucleophilic trigger in this aryne multicomponent coupling (MCC) and N-methylisatin and CO could be used as the electrophilic third components.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.9b01621 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Stereoselective Vinylogous Aza-Pummerer Reaction of β,β-Disubstituted Enesulfinamides.
Org Lett
January 2025
School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, China.
Treatment of multisubstituted NH-enesulfinamides with tosyl isocyanate (TsNCO) at room temperature results in the formation of α-tosylcarbamoyloxy -sulfenyl ketimines with high enantioselectivity. This process is believed to proceed via a vinylogous aza-Pummerer-type reaction pathway in which the sulfinyl oxygen atom in the enesulfinamides undergoes nucleophilic attack on tosyl isocyanate, triggering the subsequent transformations that enable the transfer of chirality from sulfur to carbon.
View Article and Find Full Text PDFVersatile Stimuli-Responsive Controlled Release of Pinanediol-Caged Boronic Esters for Spatiotemporal and Nitroreductase-Selective Glucose Bioimaging.
ACS Sens
January 2025
Department of Chemistry and Center for Emerging Material and Advanced Devices, National Taiwan University, Taipei 106319, Taiwan (R.O.C.).
Boronic acids have been widely applied in various biological fields, particularly achieving significant practical progress in boronic acid-based glucose sensing. However, boronic acids exhibit nonspecific binding to other nucleophiles, and the inherent lability of boronic esters in biological systems limits their further applications. Herein, we developed a stimuli-responsive controllable caging strategy to achieve photoresponsive spatiotemporally and nitroreductase-responsive cancer cell-selective glucose sensing.
View Article and Find Full Text PDFHighly stable perovskite solar cells with 0.30 voltage deficit enabled by a multi-functional asynchronous cross-linking.
Nat Commun
January 2025
Department of Electrical and Electronic Engineering, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, China.
Article Synopsis
- The commercialization of perovskite solar cells (PSCs) is hindered by their fragility and sensitivity to moisture.
- A new asynchronous cross-linking strategy using divinyl sulfone (DVS) improves perovskite crystallization and creates a durable network through post-treatment with glycerinum.
- This method boosts the efficiency of PSCs to over 25%, enhances their water resistance, reduces stress, and improves durability, marking a significant advancement in their performance and longevity.
Base-catalyzed thiol-epoxy reactions: Energetic and kinetic evaluations.
J Mol Graph Model
March 2025
Chemical Engineering Department, Ondokuz Mayıs University, 55139, Samsun, Turkey. Electronic address:
The mechanism of the base-catalyzed thiol-epoxide stage of the thiol-ene/thiol-epoxide curing process was investigated using quantum chemical tools. This study searched for conventional tertiary amines with low to medium basicity as initiators to control reaction rates and tailor industrial applications. Challenges arise from the stronger basicity of initiators, leading to an uncontrollable and short curing application period.
View Article and Find Full Text PDFPhotochemical and Collision-Induced Cross-Linking of Lys, Arg, and His to Nitrile Imines in Peptide Conjugate Ions in the Gas Phase.
J Am Soc Mass Spectrom
January 2025
Department of Chemistry, Bagley Hall, Box 351700, University of Washington, Seattle, Washington 98195-1700, United States.
We report a study of internal covalent cross-linking with photolytically generated diarylnitrile imines of N-terminal arginine, lysine, and histidine residues in peptide conjugates. Conjugates in which a 4-(2-phenyltetrazol-5-yl)benzoyl group was attached to C-terminal lysine, that we call RAAA--K, KAAA--K, and HAAA--K, were ionized by electrospray and subjected to UV photodissociation (UVPD) at 213 nm. UVPD triggered loss of N and proceeded by covalent cross-linking to nitrile imine intermediates that involved the side chains of N-terminal arginine, lysine, and histidine, as well as the peptide amide groups.
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!