898082-19-4Relevant articles and documents
A palladium-catalyzed coupling reaction of aryl nonaflates, sulfur dioxide, and hydrazines
An, Yuanyuan,Xia, Hongguang,Wu, Jie
supporting information, p. 1665 - 1669 (2016/02/09)
A facile route to synthesise N-aminosulfonamides through a palladium-catalyzed coupling reaction of aryl nonaflates, sulfur dioxide, and hydrazines is reported. This transformation proceeds in the presence of Pd(OAc)2/XantPhos, and TBAB in 1,4-dioxane at 80°C, leading to the corresponding N-aminosulfonamides in moderate to good yields. The reaction scope has been demonstrated, and good functional tolerance is observed. A plausible mechanism is proposed through the insertion of sulfur dioxide.
Metal-free aminosulfonylation of aryldiazonium tetrafluoroborates with DABCO×(SO2)2 and hydrazines
Zheng, Danqing,An, Yuanyuan,Li, Zhenhua,Wu, Jie
supporting information, p. 2451 - 2454 (2014/03/21)
The coupling of aryldiazonium tetrafluoroborates, DABCO×(SO 2)2, and hydrazines under metal-free conditions leads to the formation of aryl N-aminosulfonamides. The reaction proceeds smoothly at room temperature and shows broad functional-group tolerance. A radical process is proposed for this transformation. The coupling of aryldiazonium tetrafluoroborates, DABCO×(SO2)2, and hydrazines under metal-free conditions leads to the formation of aryl N-aminosulfonamides. The reaction proceeds under mild reaction conditions, is fast, has a broad substrate scope, and gives the products in high yiels (21 examples). A plausible mechanism that involves a radical process is also proposed. Copyright
One-pot three-component sulfone synthesis exploiting palladium-catalysed aryl halide aminosulfonylation
Richards-Taylor, Charlotte S.,Blakemore, David C.,Willis, Michael C.
, p. 222 - 228 (2014/01/06)
A palladium-catalysed aminosulfonylation process is used as the key-step in a one-pot, three-component sulfone synthesis. The process combines aryl-, heteroaryl- and alkenyl iodides with a sulfonyl unit and an electrophilic coupling fragment. The sulfonyl unit is delivered in the form of an aminosulfonamide, which then serves as a masked sulfinate. The sulfinate is combined, in situ, with an electrophilic coupling partner, such as a benzylic, allylic or alkyl halide, an electron-poor arene, or a cyclic epoxide, to provide the corresponding sulfone products in good to excellent yields. The mild reaction conditions and use of commercially available reaction components allows the easy preparation of a broad range of sulfones featuring a variety of functional groups. The process obviates the need to employ thiol starting materials, and oxidative operations.
A palladium-catalyzed reaction of aryl halides, potassium metabisulfite, and hydrazines
Ye, Shengqing,Wu, Jie
supporting information, p. 10037 - 10039 (2012/11/06)
Aryl N-aminosulfonamides could be easily produced via a palladium-catalyzed coupling of aryl halides, potassium metabisulfite, and hydrazines. Potassium metabisulfite is an excellent equivalent of sulfur dioxide in the reaction of palladium-catalyzed aminosulfonylation. The Royal Society of Chemistry 2012.
Palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides: Scope of the three-component synthesis of N-aminosulfonamides
Emmett, Edward J.,Richards-Taylor, Charlotte S.,Nguyen, Bao,Garcia-Rubia, Alfonso,Hayter, Barry R.,Willis, Michael C.
supporting information; experimental part, p. 4007 - 4014 (2012/06/04)
By using DABCO·(SO2)2, DABSO, as a solid bench-stable SO2-equivalent, the palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides has been achieved. N,N-Dialkylhydrazines are employed as the N-nucleophiles and provide N-aminosulfonamides as the products in good to excellent yields. The reactions are operationally simple to perform, requiring only a slight excess of SO 2 (1.2-2.2 equiv.), and tolerate a variety of substituents on the halide coupling partner. Variation of the hydrazine component is also demonstrated. The use of N,N-dibenzylhydrazine as the N-nucleophile delivers N-aminosulfonamide products that can be converted into the corresponding primary sulfonamides using a high-yielding, telescoped, deprotection sequence. The ability to employ hydrazine·SO2 complexes as both the N-nucleophile and SO2 source is also illustrated.
A palladium-catalyzed three-component coupling of arylboronic acids, sulfur dioxide and hydrazines
Ye, Shengqing,Wu, Jie
supporting information; experimental part, p. 7753 - 7755 (2012/09/21)
A novel and efficient route to aryl N-aminosulfonamides via a palladium-catalyzed three-component coupling of arylboronic acids, sulfur dioxide and hydrazines in the presence of a balloon of dioxygen is reported. The reaction proceeded smoothly under mild conditions and DABCO·(SO 2)2 was used as the source of sulfur dioxide.
Palladium-catalyzed aminosulfonylation of aryl halides
Nguyen, Bao,Emmett, Edward J.,Willis, Michael C.
supporting information; experimental part, p. 16372 - 16373 (2011/02/22)
The palladium-catalyzed three-component coupling of aryl iodides, sulfur dioxide, and hydrazines to deliver aryl N-aminosulfonamides is described. The colorless crystalline solid DABCO· (SO2)2 was used as a convenient source of sulfur dioxide. The reaction tolerates significant variation of both the aryl iodide and hydrazine coupling partners.
