Nickel-Catalyzed Reductive Conjugate Addition of Primary Alkyl Bromides to Enones To Form Silyl Enol Ethers

Huihui, Kierra M. M.; Shrestha, Ruja; Weix, Daniel J.

doi:10.1021/acs.orglett.6b03509

Cited by 29 publications

(16 citation statements)

References 54 publications

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“…Although 81% yield is obtained in the dimerization of benzyl bromide using 4,4 ,4 -tritertbutyl-2,2 :6 ,2 -terpyridine, substituting it by compound 1 resulted in a very low yield under the same conditions (Scheme 2, Table 1). This can be explained by the effects of the substituents onto the terpyridine, which can have important effects onto the outcome of reactions [20]. For instance, the nature of the substituents can influence the redox properties of the complex formed between the ligand and the metal [18] thus modifying the course of the reaction.…”

Section: Resultsmentioning

confidence: 99%

4′-(5-Methylfuran-2-yl)-2,2′:6′,2″-terpyridine: A New Ligand Obtained from a Biomass-Derived Aldehyde with Potential Application in Metal-Catalyzed Reactions

Husson

Guyard

2018

Molbank

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The new ligand 4′-(5-methylfuran-2-yl)-2,2′:6′,2″-terpyridine (1) was prepared in one step from 2-acetylpyridine and 5-methylfurfural. The latter is an aldehyde that can be readily obtained from biomass. The new terpyridine molecule was characterized by 1H and 13C-NMR spectroscopy as well as by elemental analyses and HR-MS. Owing to its chelating properties, this new terpyridine molecule was tested as a ligand in a metal-catalyzed reaction: The Ni-catalyzed dimerization of benzyl bromide.

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Section: Resultsmentioning

confidence: 99%

4′-(5-Methylfuran-2-yl)-2,2′:6′,2″-terpyridine: A New Ligand Obtained from a Biomass-Derived Aldehyde with Potential Application in Metal-Catalyzed Reactions

Husson

Guyard

2018

Molbank

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“…As a result, three pyridines adopt perfect coplanar conformation, allowing a good conjugation between the aromatic rings and metal cation. This feature makes tpy a potential "non-innocent" ligand, with the capability to stabilize the low valency metal, including nickel [14][15][16][17][18][19][20][21][22][23], iron [24,25], cobalt [26][27][28][29] and manganese [30,31] etc. Interesting catalytic reactivity has been obtained with these tpy-metal complexes targeting some challenging transformations, such as C-C unsaturated bond hydrofunctionalization and C-C bond formation.…”

Section: Introductionmentioning

confidence: 99%

Terpyridine-metal complexes: Applications in catalysis and supramolecular chemistry

Wei

Shi

et al. 2019

Coordination Chemistry Reviews

194

121

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As an NNN-tridentate ligand, the 2,2':6',2"-terpyridine plays an important role in coordination chemistry. With three coordination sites and low LUMO, terpyridine and its derivatives are one of the typical Pincer ligand and/or non-innocent ligands in transition metal catalysis. Interesting catalytic reactivities have been obtained with these tpy-metal complexes targeting some challenging transformations, such as CC bond formation and hydrofunctionalization. On the other hand, terpyridine ligands can form "closed-shell" octahedral complexes, which provide a linear and stable linkage in supramolecular chemistry. Numerous supramolecular architectures have been achieved using modified terpyridine ligands including Sierpiński triangles, hexagonal gasket and supramolecular rosettes. This review presents a summary of recent progress regarding transition metal-terpyridine complexes with the focus on their applications in catalysis and supramolecular structure construction. Facile synthesis of terpyridine derivatives is also described. We hope this article can serve to provide some general perspectives of the terpyridine ligand and their applications in coordination chemistry.

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“…We next explored the alkyl iodide scope using Boc-protected dehydroalanine as olefin acceptor, providing convenient access to unnatural amino acids (24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35). Also in this case, a wide variety of organyl groups bearing common functionalities such as free alcohol, alkyl chloride, silane and terminal alkyne were compatible, reflecting the mildness of the reaction conditions.…”

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confidence: 99%

Aminoalkyl radicals as halogen-atom transfer agents for activation of alkyl and aryl halides

Constantin

Zanini

Regni

et al. 2020

Science

422

282

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Organic halides are important building blocks in synthesis, but their use in (photo)redox chemistry is limited by their low reduction potentials. Halogen-atom transfer remains the most reliable approach to exploit these substrates in radical processes despite its requirement for hazardous reagents and initiators such as tributyltin hydride. In this study, we demonstrate that α-aminoalkyl radicals, easily accessible from simple amines, promote the homolytic activation of carbon-halogen bonds with a reactivity profile mirroring that of classical tin radicals. This strategy conveniently engages alkyl and aryl halides in a wide range of redox transformations to construct sp3-sp3, sp3-sp2, and sp2-sp2 carbon-carbon bonds under mild conditions with high chemoselectivity.

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Nickel-Catalyzed Reductive Conjugate Addition of Primary Alkyl Bromides to Enones To Form Silyl Enol Ethers

Cited by 29 publications

References 54 publications

4′-(5-Methylfuran-2-yl)-2,2′:6′,2″-terpyridine: A New Ligand Obtained from a Biomass-Derived Aldehyde with Potential Application in Metal-Catalyzed Reactions

4′-(5-Methylfuran-2-yl)-2,2′:6′,2″-terpyridine: A New Ligand Obtained from a Biomass-Derived Aldehyde with Potential Application in Metal-Catalyzed Reactions

Terpyridine-metal complexes: Applications in catalysis and supramolecular chemistry

Aminoalkyl radicals as halogen-atom transfer agents for activation of alkyl and aryl halides

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