Pd-Catalyzed Selective Synthesis of Cyclic Sulfonamides and Sulfinamides Using K2S2O5 as a Sulfur Dioxide Surrogate
Pd-Catalyzed Selective Synthesis of Cyclic Sulfonamides and Sulfinamides Using K2S2O5 as a Sulfur Dioxide Surrogate
复制标题
DOI：
10.1021/acs.orglett.7b00402
复制
发表时间：
2017-04-07
期刊：
影响因子：
5.2
通讯作者：
Manabe, Kei
中科院分区：
文献类型：
--
作者：
Konishi, Hideyuki;Tanaka, Hiromichi;Manabe, Kei
在钯催化下，用带有氨基的卤代芳烃和二氧化硫（SO2）替代物可以选择性地合成各种环状磺酰胺和亚磺酰胺。碱的量是决定选择性的关键。机理研究表明，亚磺酰胺最初是通过前所未有的一氧化硫的正式插入形成的，并在碘离子和DMSO的存在下氧化为磺酰胺。
A variety of cyclic sulfonamides and sulfinamides could be selectively synthesized, under Pd catalysis using haloarenes bearing amino groups and a sulfur dioxide (SO2) surrogate. The amount of base was key in determining the selectivity. Mechanistic studies revealed that sulfinamides were initially formed via an unprecedented formal insertion of sulfur monoxide and were oxidized to sulfonamides in the presence of an iodide ion and DMSO.