Journal ArticleDOI
Nickel-catalyzed cross-coupling between functionalized primary or secondary alkylzinc halides and primary alkyl halides
Anne Eeg Jensen,Paul Knochel +1 more
TLDR
In the presence of Bu(4)NI (3 equiv) and 4-fluorostyrene (20 mol %), unreactive primary and secondary alkylzinc iodides undergo nickel-catalyzed cross-couplings with various primaryAlkyl iodides or bromides allowing the synthesis of aminated products.Abstract:
In the presence of Bu4NI (3 equiv) and 4-fluorostyrene (20 mol %), unreactive primary and secondary alkylzinc iodides undergo nickel-catalyzed cross-couplings with various primary alkyl iodides or bromides. More reactive secondary dialkylzincs and the mixed zinc organometallics RZnTMSM undergo the cross-coupling reaction in the absence of Bu4NI. The bicyclic secondary diorganozinc 6 prepared via boron−zinc exchange reacts with high retention of configuration. Free NH-groups are tolerated in the cross-coupling allowing the synthesis of aminated products.read more
Citations
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Journal ArticleDOI
Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.
Journal ArticleDOI
Palladium Complexes of N-Heterocyclic Carbenes as Catalysts for Cross-Coupling Reactions—A Synthetic Chemist's Perspective
TL;DR: The basics of Pd-NHC chemistry are discussed to understand the peculiarities of these catalysts and a critical discussion on their application in C-C and C-N cross-coupling as well as carbopalladation reactions is given.
Journal ArticleDOI
Catalysts for Cross‐Coupling Reactions with Non‐activated Alkyl Halides
Anja C. Frisch,Matthias Beller +1 more
TL;DR: This Minireview highlights selected examples of metal-catalyzed coupling methods and is intended to encourage chemists to exploit the potential of these approaches in organic synthesis.
Journal ArticleDOI
Nickel-catalyzed cross coupling of non-activated alkyl halides: a mechanistic perspective
TL;DR: The recent development of nickel-catalyzed coupling of non-activated alkyl halides is reviewed and the current understanding of the mechanism of these coupling reactions is highlighted.
Journal ArticleDOI
Chiral olefins as steering ligands in asymmetric catalysis.
TL;DR: This work highlights the increasing number of chiral chelating olefin ligands as well as their application in a variety of metal-catalyzed transformations.
References
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Journal ArticleDOI
Nickel and palladium complex catalyzed cross-coupling reactions of organometallic reagents with organic halides
TL;DR: The discovery in 1972 by two research groups that dihalodiphosphinenickel(II) complexes exhibit extremely high catalytic activity for selective cross-coupling of Grignard reagents with sp2-carbon halides has aroused wide-spread interest in application in organic synthesis of this type and related reactions involving other organometallics than Grignards and not only nickel but also palladium complexes as catalysts as mentioned in this paper.
Journal ArticleDOI
Palladacycles: Efficient New Catalysts for the Heck Vinylation of Aryl Halides
Wolfgang A. Herrmann,Christoph Brossmer,Claus-Peter Reisinger,Thomas Riermeier,Karl Öfele,Matthias Beller +5 more
TL;DR: Cyclopalladated complexes of the general formula [Pd2(μ-L)2(PC)2] (L = bridging ligand, e.g. OAc, Cl, Br, I; PC = cyclometallated P donor) are highly efficient catalysts for the Heck vinylation of aryl halides.
Journal ArticleDOI
Nickel-Catalyzed Cyclizations, Couplings, and Cycloadditions Involving Three Reactive Components
TL;DR: This account outlines work primarily from the author's laboratory on the development of nickel-catalyzed multicomponent coupling processes, an overview of new synthetic methods, a discussion of potential mechanisms, and a description of applications in complex-molecule synthesis are provided.
Journal ArticleDOI
Fluoride-Mediated Boronic Acid Coupling Reactions
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