title: Palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides: scope of the three-component synthesis of N-aminosulfonamides.
abstract: By using DABCO·(SO(2))(2), DABSO, as a solid bench-stable SO(2)-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·SO(2) complexes as both the N-nucleophile and SO(2) source is also illustrated.
authors.affiliation: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK.
authors.forename: Edward J
authors.initials: EJ
authors.lastname: Emmett
authors.forename: Charlotte S
authors.initials: CS
authors.lastname: Richards-Taylor
authors.forename: Bao
authors.initials: B
authors.lastname: Nguyen
authors.forename: Alfonso
authors.initials: A
authors.lastname: Garcia-Rubia
authors.forename: Barry R
authors.initials: BR
authors.lastname: Hayter
authors.forename: Michael C
authors.initials: MC
authors.lastname: Willis
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D006219:Halogens / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013451:Sulfonic Acids / Q000737:chemistry*
chemical_list: D000475:Alkenes; D006219:Halogens; D013451:Sulfonic Acids; D010165:Palladium; C005741:sulfamic acid