- Palladium-catalyzed aminosulfonylation of aryl halides
-
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.
- Nguyen, Bao,Emmett, Edward J.,Willis, Michael C.
-
-
Read Online
- Palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides: Scope of the three-component synthesis of N-aminosulfonamides
-
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.
- 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)
-
- A palladium-catalyzed reaction of aryl halides, potassium metabisulfite, and hydrazines
-
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.
- Ye, Shengqing,Wu, Jie
-
supporting information
p. 10037 - 10039
(2012/11/06)
-