673-40-5Relevant articles and documents
Metal-Free Visible-Light Synthesis of Arylsulfonyl Fluorides: Scope and Mechanism
Louvel, Dan,Chelagha, Aida,Rouillon, Jean,Payard, Pierre-Adrien,Khrouz, Lhoussain,Monnereau, Cyrille,Tlili, Anis
supporting information, p. 8704 - 8708 (2021/05/17)
The first metal-free procedure for the synthesis of arylsulfonyl fluorides is reported. Under organo-photoredox conditions, aryl diazonium salts react with a readily available SO2 source (DABSO) to afford the desired product through simple nucleophilic fluorination. The reaction tolerates the presence of both electron-rich and -poor aryls and demonstrated a broad functional group tolerance. To shed the light on the reaction mechanism, several experimental techniques were combined, including fluorescence, NMR, and EPR spectroscopy as well as DFT calculations.
Alternative method for the synthesis of triazenes from aryl diazonium salts
Abrams
supporting information, (2021/05/10)
An alternative mild method for access to 1-aryl-3,3-dimethyl alkyl triazenes is described. This protocol employs the dropwise addition of a methanolic solution of a carboxylate (RCO2M) or carbonate (CO32?) to a gently heated DMF solution containing an aryl diazonium salt (ArN2+), that had been previously isolated. Presumably homolysis of the weak N–O bond of diazo ether adducts formed in this operation initiates radical pathways that lead to the generation of triazene product. DMF serves as not only a one-electron donor to the diazonium salts employed in this process, but also as a source of dimethylamine radicals that act as a nucleophilic coupling partner. The reaction provides modest yields (ca. 20–40%) across an array of aryl diazonium salts that contain various substitution. Furthermore this unique approach to triazenes contrasts with traditional methods that employ dimethyl amine in reagent form which directly couples with diazonium salts. Seemingly, only one other example employing somewhat similar reaction conditions to this current investigation en route to triazenes has been reported, albeit with lower yields and for one representative example furnished as a side-product. The current work here improves upon the efficiency of this reported result, and further expands the reaction scope.
Copper-mediated tandem ring-opening/cyclization reactions of cyclopropanols with aryldiazonium salts: Synthesis of: N -arylpyrazoles
Liu, Jidan,Xu, Erjie,Jiang, Jinyuan,Huang, Zeng,Zheng, Liyao,Liu, Zhao-Qing
supporting information, p. 2202 - 2205 (2020/02/26)
A general method for the synthesis of structurally diverse N-arylpyrazoles from readily available cyclopropanols and aryldiazonium salts is disclosed. The reaction was conducted at room temperature within minutes with a broad substrate scope and excellent regioselectivity.
