A copper-catalyzed aminosulfonylation of aryldiazonium tetrafluoroborates, DABCO·(SO), and N-chloroamines is described. This coupling reaction provides an efficient and simple approach to a wide range of sulfonamides in moderate to good yields under mild conditions. Mechanistic investigation suggests that a radical process and transition-metal catalysis are merged in this tandem reaction.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.8b00093 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Catalyst-Free Radical Carbosulfonylation of Enamides with Indoles, Aryldiazonium Tetrafluoroborates, and DABCO·(SO).
Org Lett
October 2024
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Nanjing Tech University, Nanjing 211816, China.
Article Synopsis
- Researchers created a new method for carbosulfonylation of enamides using four key components without needing a catalyst, producing various β-amidosulfone products.
- This method operates under mild conditions, is efficient with high yields, and can work with many different substrates, making it a more environmentally friendly option.
- The study also suggests that the transformation follows a radical tandem reaction process, as indicated by their mechanism investigations.
Rapid synthesis of azoindolizine derivatives via aryldiazonium salts.
Turk J Chem
March 2024
Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, Turkiye.
A practical, rapid, and efficient method for the synthesis of azoindolizine derivatives via aryldiazonium salts with excellent yields was reported. Firstly, the corresponding aniline derivatives were synthesized via a simple and rapid method. Then, the optimal reaction conditions were investigated using a variety of protic and aprotic solvents that demonstrating the robustness of the approach.
View Article and Find Full Text PDFFour-Component Radical 1,2-Selenosulfonylation of Allenes.
Org Lett
July 2024
School of Materials Science and Chemical Engineering, Ningbo University, Zhejiang, 315211, China.
Selenosulfones, as pivotal pharmaceutical molecule frameworks, have become a research hotspot in modern organic synthesis due to their vital need for efficient preparation. Herein, we have developed an iron-catalyzed four-component controllable radical tandem reaction of allenes involving cycloketone oxime esters, 1,4-diazabicyclo[2.2.
View Article and Find Full Text PDFElectro-oxidative coupling of Bunte salts with aryldiazonium tetrafluoroborates: a benign access to unsymmetrical sulfoxides.
Org Biomol Chem
January 2024
Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi 221005, India.
An electrochemical strategy for the synthesis of unsymmetrical sulfoxides has been explored using Bunte salts and aryldiazonium tetrafluoroborates under constant current electrolysis at room temperature. In addition to being eco-safe and using mild conditions, the present protocol is free from the use of metal/oxidant, and is endowed with a broad substrate scope and good functional group tolerance.
View Article and Find Full Text PDFAnnulative Aminosulfonylation of Unactivated Alkenes for Accessing Pyrazolines via Multicomponent SO Insertion.
J Org Chem
August 2023
School of Chemistry & Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, China.
A direct arylsulfonylation of β,γ-unsaturated hydrazones method, in which sulfonated pyrazolines are accessed by a three-component reaction of β,γ-unsaturated hydrazones, DABSO, and aryldiazonium tetrafluoroborates, has been developed without external oxidants or catalysts. This transformation is triggered by the formation of arylsulfonyl radicals in situ from the reaction of aryldiazonium tetrafluoroborates and DABSO, and is enabled by controllable generation of C center radical, in which DABSO was utilized as the sulfone source and an oxidant in this radical-mediated cascaded reaction. A wide range of substrates can be applied in this process to afford pyrazolines in good yield, and it is amenable for gram-scale synthesis.
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!