Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction
Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction
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DOI：
10.1021/jacs.1c04215
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发表时间：
2021-06-28
影响因子：
15
通讯作者：
Yamaguchi, Junichiro
中科院分区：
文献类型：
--
作者：
Isshiki, Ryota;Kurosawa, Miki B.;Yamaguchi, Junichiro
以镍为催化剂，通过芳基硫醚与多种芳基亲电试剂的芳基交换反应合成了芳基硫醚。通过使用2-吡啶基硫醚作为硫醚供体，该反应实现了芳基硫醚的合成，而不使用有气味和有毒的硫醇。使用能够裂解和形成芳基-S键的Ni/dcypt催化剂对于2-吡啶基硫化物和芳基亲电试剂（包括芳香酯、芳烃醇衍生物和芳基卤化物）之间的芳基交换反应是重要的。机理研究表明，Ni/dcypt可以同时进行氧化加成的芳基硫化物和芳香族酯，然后通过生成的芳基-Ni-SR和芳基-Ni-OAr物种之间的配体交换，以提供芳基交换的化合物。
A Ni-catalyzed aryl sulfide synthesis through an aryl exchange reaction between aryl sulfides and a variety of aryl electrophiles was developed. By using 2-pyridyl sulfide as a sulfide donor, this reaction achieved the synthesis of aryl sulfides without using odorous and toxic thiols. The use of a Ni/dcypt catalyst capable of cleaving and forming aryl-S bonds was important for the aryl exchange reaction between 2-pyridyl sulfides and aryl electrophiles, which include aromatic esters, arenol derivatives, and aryl halides. Mechanistic studies revealed that Ni/dcypt can simultaneously undergo oxidative additions of aryl sulfides and aromatic esters, followed by ligand exchange between the generated aryl-Ni-SR and aryl-Ni-OAr species to furnish aryl exchanged compounds.