Palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides: scope of the three-component synthesis of N-aminosulfonamides
Palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides: scope of the three-component synthesis of N-aminosulfonamides
复制标题
DOI：
10.1039/c2ob07034k
复制
发表时间：
2012-01-01
影响因子：
3.2
通讯作者：
Willis, Michael C.
中科院分区：
文献类型：
--
作者：
Emmett, Edward J.;Richards-Taylor, Charlotte S.;Willis, Michael C.
以DABCO中心点（SO_2）（2），DABSO作为固体稳定的SO_2-等价物，实现了钯催化芳基、烯基和杂芳基卤代物的氨磺酰化反应。N，N-二烷基肼用作N-亲核试剂，并以良好至优异的产率提供N-氨基磺酰胺作为产物。该反应操作简单，只需要稍微过量的SO2（1.2-2.2当量），并容许卤化物偶联配偶体上的各种取代基。肼组分的变化也被证明。使用N，N-二苄基肼作为N-亲核试剂提供N-氨基磺酰胺产物，所述产物可以使用高产率、套叠的脱保护序列转化为相应的伯磺酰胺。还说明了采用肼中心点SO2络合物作为N-亲核试剂和SO2源的能力。
By using DABCO center dot(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 SO2 (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 center dot SO2 complexes as both the N-nucleophile and SO2 source is also illustrated.