The University of Osaka · Chemistry
Professor Nobuaki Kambe's research lab specializes in the development of innovative transition metal-catalyzed cross-coupling reactions, with a particular focus on activating inert C–H and C–X (X = F, Cl, Br, I, OTs, OMs) bonds in organic synthesis. The lab pioneers methods for functionalizing sp³-hybridized carbon centers, including alkyl halides and fluorides, using novel ligands and catalytic systems such as Cu- and Ni-based catalysts. A key theme is the design of selective transformations—such as sulfenylation, sulfonylation, and C–C bond formation—enabled by directing groups like 8-aminoquinoline, expanding the scope of late-stage functionalization. The lab also explores the use of organometallic reagents, including Grignard and telluride-based reagents, for efficient and chemoselective transformations under mild conditions.
Figures are computed from collected data and may differ slightly.
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.
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