6148-75-0Relevant articles and documents
Iron-catalyzed synthesis of arylsulfinates through radical coupling reaction
Zhang, Weixi,Luo, Meiming
supporting information, p. 2980 - 2983 (2016/02/19)
A novel strategy for installation of a sulfonyl fragment into arenes has been accomplished via an iron-catalyzed radical coupling reaction. Arene radicals derived from diaryliodoniums via single electron transfer reaction combine with sulfoxylate anion radicals readily generated from commercially available rongalite (HOCH2SO2Na·2H2O) to afford arylsulfinates efficiently at room temperature. In this protocol, a broad range of functional groups are tolerated to give products in good yields.
Mechanism of Azo Coupling Reactions: Part XXXVI. The Relationship between the Structure and the Catalytic Activity of Anionic Phase-Transfer Catalysts in Azo Coupling Reactions
Iwamoto, Hidetoshi,Kobayashi, Hiroshi,Murer, Pius,Sonoda, Takaaki,Zollinger, Heinrich
, p. 2590 - 2602 (2007/10/02)
A series of 15 sodium arenesulfonates containing alkyl, hydroxyl or methoxyl groups was investigated for the phase-transfer catalysis of the azo coupling reaction of the 4-methoxybenzenediazonium ion (1) with 1,3,5-trimethoxybenzene (2) in a dichloromethane/water two-phase system, in which the yields, initial reaction rates and influence of the decomposition of the diazonium ion 1 were measured.The influence of counter anions on the partition coefficient (α) for the diazonium ion 1 in a dichloromethane/water system, and the effects of the solvent polarity and structure of counter anions on the reaction rates of the azo coupling of the diazonium ion 1 with N,N-dimethylaniline (4) and 1,3,5-trimethoxybenzene (2) in organic solvents and in dichloromethane/water system, were investigated.The symmetrical structure of the tetrakisborate (TFPB) anion was proved to be an essential factor regarding the remarkably high α for the diazonium ion 1 ion-paired with TFPB.The looseness and tightness of ion pairs of highly desolvated diazonium ion 1 in a nonpolar organic media is one of the most significant factors concerning the reactivity of the diazonium ion 1 in a rate-limiting azo coupling with 4.In a reaction of the diazonium ion 1 with 2 in a dichloromethane/water system, however, the amount of saturated water and/or additives in the dichloromethane phase, which serves as a base for the rate-limiting deprotonation, becomes the most influential factor for an effective azo coupling reaction under phase-transfer catalysis conditions.