Nickel-Catalyzed Cross-Coupling Reaction of Aryl Sulfoxides with Arylzinc Reagents: When the Leaving Group is an Oxidant

被引：45

作者：

Yamamoto, Keita ^{[1
]}

Otsuka, Shinya ^{[1
]}

Nogi, Keisuke ^{[1
]}

Yorimitsu, Hideki ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

来源：

ACS CATALYSIS | 2017年 / 7卷 / 11期

关键词：

Negishi coupling nickel catalyst; aryl sulfoxide; arylzinc; alkanesulfenate anion; BOND-FORMING REACTIONS; GRIGNARD-REAGENTS; C-C; ORGANIC-COMPOUNDS; MILD CONDITIONS; CARBON-SULFUR; PALLADIUM; ACTIVATION; SULFIDES; ARYLATION;

D O I：

10.1021/acscatal.7b02347

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

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.

引用

页码：7623 / 7628

页数：6

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