The University of Osaka · 화학
Nobuaki Kambe 교수의 연구실은 주로 탄소-할로젠 결합의 고도로 선택적인 변환과 새로운 교차커플링 반응을 중심으로 한 유기합성화학을 연구하고 있습니다. 특히 알킬 할라이드 및 C-F 결합을 효율적으로 기능화하여 C-C, C-X(여기서 X는 S, Se, Te 등) 결합을 형성하는 데에 초점을 맞추고 있으며, 구리 및 니켈 촉매를 활용한 고도로 선택적인 허브리드 반응 개발에 기여하고 있습니다. 이는 약물화학 및 고분자 화학 분야에서 응용 가능한 유용한 전구체를 제공합니다.
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Cross-coupling reactions have become indispensable tools for creating carbon-carbon (or heteroatom) bonds in organic synthesis. Like in other important transition metal catalyzed reactions, such as metathesis, addition, and polymerization, unsaturated compounds are usually employed as substrates for cross-coupling reactions. However during the past decade, a great deal of effort has been devoted to the use of alkyl halides as saturated compounds in cross-coupling reactions, which has resulted in
Gelungene Verbindung: Die Cu-katalysierte Kreuzkupplung zwischen primären Alkylhalogeniden und primären, sekundären und tertiären Alkyl- sowie Phenyl-Grignard-Reagentien verläuft in THF unter Rückfluss in Gegenwart von 1-Phenylpropin effizient (siehe Schema). Die Reaktion gelingt auch mit Alkylmesylaten (OMs) und -tosylaten (OTs). Die Alkyl-X-Reaktivitäten gegenüber dem Grignard-Reagens nehmen in der Reihenfolge X=Cl<F<OMs<OTs<Br zu. Supporting information for this article is available on the WW
Compounds of the type Rli , with R PhC°C, PhCH 2 Ph, CH 2 CHCH 2 , alkyl, Me 3 SiCH 2 , PhCH 2 OCH 2 , etc., can be generated in an indirect way by the route shown below. In a one‐pot procedure, the tellurides are formed directly from alkyl halides and tellurolates RTeLi. The procedure particularly valuable when conventional lithium‐halogen exchange is not possible. equation image
A simple method for the conversion of (sp(3))C-F bonds of alkyl fluorides to (sp(3))C-X (X = Cl, C, H, O, S, Se, Te, N) bonds has been achieved by the use of a hexane solution of organoaluminum reagents having Al-X bonds.
The direct sulfenylation and sulfonylation of (sp(2))C-H bonds of benzamide derivatives were achieved using a Ni catalyst with the aid of an 8-aminoquinoline moiety as a bidentate directing group. These protocols represent a convenient route for the formation of valuable diaryl sulfides and sulfones in moderate to excellent yields.
A facile method for the conversion of C-F bonds of benzotrifluorides to C-C bonds has been developed using aluminium reagents in the absence of catalysts.
A new method for the regioselective three-component cross-coupling of alkyl halides, alkynes, or enynes with organomagnesium or organozinc reagents in the presence of a nickel catalyst and a dppb ligand has been developed.
The cross-coupling of Grignard reagents with alkyl bromides and tosylates has been achieved by the use of eta(3)-allylnickel and eta(3)-allylpalladium complexes as catalysts.
