Nickel/Cobalt-Catalyzed C(sp3)-C(sp3) Cross-Coupling of Alkyl Halides with Alkyl Tosylates

被引：64
|
作者：
Komeyama, Kimihiro [1 ]
Michiyuki, Takuya [1 ]
Osaka, Itaru [1 ]
机构：
[1] Hiroshima Univ, Grad Sch Engn, Dept Appl Chem, 1-4-1 Kagamiyama, Higashihiroshima, Hiroshima 7398527, Japan
来源：
ACS CATALYSIS | 2019年 / 9卷 / 10期
关键词：
C(sp(3))-C(sp(3)) Cross-Coupling; nickel catalyst; cobalt catalyst; alkyl tosylate; alkyl halide; SUBEROYLANILIDE HYDROXAMIC ACID; GRIGNARD-REAGENTS; METHYL TRANSFER; BROMIDES; SULFONYLATION; FLUORIDES; ALCOHOLS; FUNCTIONALIZATION; COMPLEX; DIOLS;
D O I：
10.1021/acscatal.9b03352
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：
The C(sp(3))-C(sp3) Cross-Coupling of alkyl halides with alkyl tosylates has been developed by employing a combination of nickel and nucleophilic cobalt catalysts in the presence of a manganese reductant. This method provides a straightforward route to a diverse set of not only secondary-primary but also primary-primary C(sp(3))-C(sp(3)) linkages under mild conditions without using alkyl-metallic reagents. Mechanistic studies suggest the formation of alkyl radicals from both alkyl halides and alkyl tosylates. Additionally, cross-coupling could be applied to the short-step synthesis of a histone deacetylase inhibitor, Vorinostat.
引用
收藏
页码：9285 / 9291
页数：13
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