10151-46-9Relevant articles and documents
Copper-catalyzed: S -methylation of sulfonyl hydrazides with TBHP for the synthesis of methyl sulfones in water
Yang, Yu,Bao, Yajie,Guan, Qianqian,Sun, Qi,Zha, Zhenggen,Wang, Zhiyong
, p. 112 - 116 (2017)
A copper-catalyzed S-methylation of sulfonyl hydrazides with TBHP was efficiently developed, providing a variety of methyl sulfones with good to excellent yields. The reaction can be carried out in water smoothly without any ligand or additive under mild conditions and this catalyst-in-water can be recycled several times.
Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides
Mulina, Olga M.,Zhironkina, Nataliya V.,Paveliev, Stanislav A.,Demchuk, Dmitry V.,Terent'Ev, Alexander O.
, p. 1818 - 1824 (2020)
Sulfonylated N-unsubstituted enamines were synthesized through a chain of chemical and electrochemical transformations via sulfonylation of vinyl azides. The disclosing of the N-unsubstituted enamines synthesis was based on a unique property of the azido group, which is its ability to eliminate the N2 molecule. Furthermore, a formal paradox is observed: A double bond reacts and a double bond is retained. Electrosynthesis proceeded in an undivided cell equipped with a graphite anode and a stainless steel cathode; NH4I was used as a supporting electrolyte.
Electrochemical Annulation-Iodosulfonylation of 1,5-Enyne-containing para-Quinone Methides (p-QMs) to Access (E)-Spiroindenes
Zuo, Hang-Dong,Zuo, Hang-Dong,Hao, Wen-Juan,Zhu, Chi-Fan,Zhu, Chi-Fan,Guo, Cheng,Tu, Shu-Jiang,Jiang, Bo
, p. 4471 - 4477 (2020)
A new electrochemical three-component annulation-iodosulfonylation of 1,5-enyne-containing para-quinone methides (p-QMs) has been established by using available arylsulfonyl hydrazides and potassium iodide under environmentally benign conditions. The electrosynthesis offers sustainable and efficient access to construct spirocyclohexadienone-containing (E)-indenes without any additional catalyst or oxidant through a sulfonyl-radical-triggered 1,6-addition and an I+-mediated ipso-cyclization cascade. Notably, potassium iodide plays the triple role of an electrolyte, a redox catalyst, as well as an iodination reagent.
Synthesis of 3,4-Dihydrobenzo[f]phthalazines via Iodine/tert-Butyl Hydroperoxide-Mediated Annulation Cascade of Yne-Allenones
Fu, Rong,Li, Meng-Fan,Zhou, Peng,Hao, Wen-Juan,Tu, Shu-Jiang,Jiang, Bo
, p. 2280 - 2285 (2019)
An iodine (I2)/tert-butyl hydroperoxide (TBHP)-mediated annulation cascade between yne-allenones and sulfonyl hydrazides has been established, in which a wide set of dihydrobenzo[f]phthalazines were synthesized through one-pot, two-step strategy under metal-free conditions. The synthetic utility of these transformations leads to subsequent C?C and C?N bond-forming reactions to effectively build up functional aza-heterocycle with potential significance. (Figure presented.).
Gold-Catalyzed Dehydrazinative C(sp)–S Coupling Reactions of Arylsulfonyl Hydrazides with Ethynylbenziodoxolones for Accessing Alkynyl Sulfones
Shinde, Popat S.,Patil, Nitin T.
, p. 3512 - 3515 (2017)
A gold(III)-catalyzed dehydrazinative coupling reaction between arylsulfonyl hydrazides and ethynylbenziodoxolone reagents was realized for the synthesis of alkynyl sulfones. The scope and versatility of the reaction were demonstrated by the efficient synthesis of 23 derivatives with diverse structural features.
Electrochemical Sulfonylation-Induced Lactonization of Alkenes: Synthesis of Sulfonyl Phthalides
Chen, Qianjin,Li, Guodong,Xu, Bo,Yang, Jiajun,Yu, Ke
, p. 1208 - 1217 (2022/01/27)
An electrochemical cascade sulfonylation and lactonization process of alkenes and a most widely used arylsulfonylation reagent─sulfonyl hydrazines─was developed for the first time. This electrochemical sulfonyl lactonization avoided the use of toxic metal
Dual Roles of Rongalite: Reductive Coupling Reaction to Construct Thiosulfonates Using Sulfonyl Hydrazides
Zhang, Guofu,Fan, Qiankun,Zhao, Yiyong,Wang, Huimin,Ding, Chengrong
supporting information, p. 81 - 85 (2020/11/03)
A tunable and practical transformation of structurally diverse sulfonyl hydrazides into thiosulfonates in the presence of Rongalite (NaHSO 2·CH 2O) was developed. Transition-metal-free conditions, operational simplicity, and readily available reagents are the striking features of this protocol. It is the first example for the synthesis of thiosulfonates using sulfonyl hydrazides with the assistance of reductant. Additionally, the mechanistic studies revealed that this transformation probably undergoes via a reducing-coupling pathway.