Herein, we report a C−S cross‐coupling reaction between alkyl thiols or aryl thiols and ortho‐substituted arylboronic acids that proceeds in the presence of an inexpensive and ligand‐free NiCl₂ ⋅ 6H₂O salt and N‐methylmorpholine, a weak base, at 25 °C in air. The presence of coordinating and electron‐withdrawing groups at the ortho‐position of the arylboronic acids played a crucial role in determining the efficiency of the reaction. X‐ray crystallographic analysis revealed that the [NiCl₂(DMF)₂(H₂O)₂] complex was formed in‐situ. The complex is an excellent precursor of the active nickel species. The reaction offers an extremely mild and operationally convenient method to access a wide variety of alkyl aryl sulfides and diaryl sulfides without using expensive transition metals, such as palladium, gold, and rhodium, and specialized and expensive ligands.

中文翻译：

---

硫醇与邻位取代的芳基硼酸之间的镍（II）介导的CS交叉偶联

在本文中，我们报道了烷基硫醇或之间的C-S的交叉偶联反应芳基硫醇和邻-取代的芳基硼酸，在廉价的和配体游离的NiCl的存在下进行₂  ⋅6H ₂ ö盐和Ñ甲基吗啉，弱于25°C的空气中。在芳基硼酸的邻位存在配位基团和吸电子基团，对确定反应效率起着至关重要的作用。X射线晶体学分析表明[NiCl ₂（DMF）₂（H ₂ O）₂ ]络合物是原位形成的。该络合物是活性镍物质的极好的前体。该反应提供了一种极其温和且操作简便的方法，无需使用昂贵的过渡金属（例如钯，金和铑）以及专用且昂贵的配体，即可获得各种烷基芳基硫醚和二芳基硫醚。