Pentafluorosulfanyl chloride (SF Cl) is the most prevalent reagent for the incorporation of SF group into organic compounds. However, the preparation of SF Cl often relies on hazardous reagents and specialized apparatus. Herein, we described a safe and practical synthesis of a bench-stable and easy-to-handle solution of SF Cl in n-hexane under gas-reagent-free conditions. The synthetic application of SF Cl was demonstrated through the unprecedented reaction with diazo compounds. The chemoselective hydro- and chloropentafluorosulfanylations of α-diazo carbonyl compounds were developed in the presence of K PO or copper catalyst, respectively. These reactions provide a direct and efficient access to various α-pentafluorosulfanyl carbonyl compounds of high value for potential applications.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/anie.202103606 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Accelerated aging modulates the toxicological properties of the diazo tattoo pigment PO13.
Sci Rep
January 2025
Univ. Grenoble Alpes, CEA, CNRS, Grenoble INP, SyMMES, Grenoble, F-38000, SyMMES, France.
Pigment particles used in tattooing may exert long terms effect by releasing diffusible degradation products. In the present work, aqueous suspensions of the organic orange diazo pigment PO13 were aged by exposure to simulated sunlight at 40 °C. The morphology and the surface charge of PO13 particles were barely modified upon aging, but primary particles were released by de-agglomeration.
View Article and Find Full Text PDFThe Cascade Reaction Chemistry of Diazo Compounds with Intentionally Designed Alkene to Access Esterified Heterocycles.
Org Lett
January 2025
College of Pharmacy, Chongqing Medical University, Chongqing 400016, China.
Exploration of the cascade reactivity of diazo compounds with alkenes is a challenging and largely unmet goal. Herein, we disclose a light-mediated de novo synthesis of esterified heterocycles under mild conditions. The reaction displays a broad functional group tolerance, including a wide variety of alkenes, diazo compounds, and some bioactive molecules.
View Article and Find Full Text PDFEffect of Typha angustifolia, feeding modes and intermittent aeration on the performance of hybrid constructed wetland systems treating Reactive Black 5 diazo dye wastewater.
Environ Sci Pollut Res Int
December 2024
Department of Civil Engineering, Indian Institute of Technology Guwahati, Guwahati, Assam, 781039, India.
The current research assessed the effectiveness of four hybrid constructed wetland (HCW) systems for the remediation of synthetic dye wastewater with Reactive Black 5 (RB5) azo dye. All HCW systems had identical configurations, consisting of a horizontal CW followed by a vertical CW, and operated under diverse conditions such as the presence of plants (Typha angustifolia), feeding modes (batch and continuous) and intermittent aeration (4 h day). Anaerobic-aerobic conditions simulated within the HCW systems were crucial in removing the pollutants from synthetic dye wastewater.
View Article and Find Full Text PDFSynthesis of Carboxylic Acids Containing α-All-Carbon Quaternary Centers from Diazo Compounds and Trialkylboranes.
J Org Chem
December 2024
Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.
The construction of C-C bonds to form all-carbon quaternary centers remains a significant challenge in synthetic chemistry. Herein, we report a tandem process involving a 1,2-migration of a tetra-coordinated boron intermediate followed by a Claisen rearrangement of the boron enolate, achieved through a reaction between allyl diazoacetates and trialkylboranes. The transformation forms two C-C bonds at the carbenic position of diazo substrate in a single-step operation under neutral conditions.
View Article and Find Full Text PDFA Formal 1,2-Stevens Rearrangement of Thioester Ylides as a Single-Atom Molecular Editing Tool.
Org Lett
December 2024
University of Belgrade, Faculty of Chemistry, Studentski trg 16, P.O. Box 51, 11158 Belgrade 118, Serbia.
A rhodium-catalyzed reaction of thioesters with diazo reagents was recognized as a powerful and unprecedented tool for single-atom molecular editing by the insertion of a single carbon atom into the C(O)─S thioester bond, thereby leading to various α-thioketones possessing a quaternary carbon atom. A selective and precise defunctionalization of the polyfunctionalized products further demonstrated the synthetic utility of the reaction for the synthesis of more common structural classes of compounds.
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!