Nickel-Catalyzed Cross-Coupling Reaction of Aryl Sulfoxides with Arylzinc Reagents: When the Leaving Group is an Oxidant
Nickel-Catalyzed Cross-Coupling Reaction of Aryl Sulfoxides with Arylzinc Reagents: When the Leaving Group is an Oxidant
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DOI：
10.1021/acscatal.7b02347
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发表时间：
2017-10
期刊：
影响因子：
12.9
通讯作者：
Keita Yamamoto;S. Otsuka;K. Nogi;H. Yorimitsu
中科院分区：
文献类型：
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作者：
Keita Yamamoto;S. Otsuka;K. Nogi;H. Yorimitsu
研究了镍催化芳基甲基亚砜与芳基锌试剂的根志型交叉偶联反应。通过芳基锌试剂的氧化均偶联，消耗催化氧化的甲磺酸阴离子，实现催化剂的平稳周转。以芳基溴化镁、溴化锌和溴化锂为原料制备的芳基锌试剂收率较高，其他工艺制备的芳基锌试剂的反应活性较低。比较了芳基甲基亚砜与典型芳基（伪）卤化物的反应性。
Nickel-catalyzed Negishi-type cross-coupling of aryl methyl sulfoxides with arylzinc reagents has been developed. By consuming the catalyst-oxidizing methanesulfenate anion through oxidative homocoupling of the arylzinc reagent, smooth catalyst turnover could be executed. Arylzinc reagents prepared from arylmagnesium bromide, zinc bromide, and lithium bromide were optimal to afford the products in good to high yields, while arylzinc reagents prepared through other procedures showed lower reactivities. The reactivity of aryl methyl sulfoxide was compared with that of typical aryl (pseudo)halides.