An efficient method was developed for the synthesis of unsymmetrical -arylsulfamides using sulfamoyl azides and arylboronic acids in the presence of 10 mol% of copper chloride as the catalyst. The reaction was facilitated in MeOH in an open flask at room temperature. Unlike the coupling of sulfamides and boronic acids, the use of sulfamoyl azides was found to be beneficial with respect to the yield and reaction time.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9059883 | PMC |
| http://dx.doi.org/10.1039/c8ra09219b | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Remote Radical Azidation of Unactivated C(sp)-H Bonds in Sulfamoyl Azides.
Org Lett
May 2024
School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China.
An efficient method for remote radical C(sp)-H azidation at unactivated sites is described. C-H functionalization proceeds via intramolecular 1,5-hydrogen atom transfer to N-centered radicals that are generated via azido group transfer and/or fragmentation. The readily installed sulfamoyl azide serves as both an amidyl radical precursor and an azido source.
View Article and Find Full Text PDFNew Mode of Asymmetric Induction for Enantioselective Radical -Heterobicyclization via Kinetically Stable Chiral Radical Center.
Chem
January 2024
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States.
Enantioselective radical -heterobicyclization of -allylsulfamoyl azides have been developed via metalloradical catalysis (MRC). The Co(II)-based catalytic system can homolytically activate the organic azides with varied electronic and steric properties for asymmetric radical -heterobicyclization under mild conditions without the need of oxidants, allowing for stereoselective construction of chiral [3.1.
View Article and Find Full Text PDFConvergent synthesis of thiodiazole dioxides from simple ketones and amines through an unusual nitrogen-migration mechanism.
Chem Sci
December 2023
Department of Chemistry, University of California Berkeley CA 94720 USA
We report the modular preparation of dihydro-1,2,5-thiodiazole dioxide heterocycles starting from methyl ketones and primary amines. This one-pot, three-component coupling employs 2,3-dimethylimidazole-1-sulfonyl azide triflate as a coupling reagent and oxidant. The transformation is scalable and various ketones and amines can be used, yielding thiodiazole dioxide products in up to 89% yield.
View Article and Find Full Text PDFSynthesis of dienes from pyrrolidines using skeletal modification.
Nat Commun
November 2023
Institute of Chemistry and BioMedical Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China.
Saturated N-heterocyclic pyrrolidines are common in natural products, medicinal compounds and agrochemicals. However, reconstruction of their skeletal structures creating new chemical space is a challenging task, and limited methods exist for this purpose. In this study, we report a skeletal modification strategy for conversion of polar cyclic pyrrolidines into nonpolar linear dienes through a N-atom removal and deconstruction process.
View Article and Find Full Text PDFContinuous Flow Synthesis of -Sulfonyl-1,2,3-triazoles for Tandem Relay Cu/Rh Dual Catalysis.
J Org Chem
January 2023
Department of Chemistry and Nanoscience, Ewha Womans University, Seoul03760, South Korea.
The continuous flow synthesis of -sulfonyl-1,2,3-triazoles, which are convenient reactive azavinyl carbene precursors, for tandem relay Cu/Rh dual catalysis has been developed. Most reactions readily proceeded at 75 °C in a short residence time of 13.09 min in the presence of 2.
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!