Cobalt-Catalyzed C-C Bond-Forming Reactions via Chelation-Assisted C-H Activation

Yoshikai, Naohiko

doi:10.5059/yukigoseikyokaishi.72.1198

Cited by 17 publications

(4 citation statements)

References 60 publications

(28 reference statements)

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“…Because the coordination of a directing group to a metal center brings the catalyst into close proximity with the substrate, site selective C–H bond activation proceeds more smoothly. Given the large number of literature reports, directed C–H bond activation studies have focused on either monodentate or bidentate directing groups for assistance. − The ease of metal coordination to a bidentate directing group over a monodentate directing group and the tunable coordinating properties has resulted in an increase in their use. A huge number of studies based on this strategy have appeared in the literature following the discovery of N , N ′-bidentate directing group-assisted C–H bond functionalizations in 2005. − The tuning of suitable bidentate directing groups and the selection of appropriate metal catalysts are important issues for specific types of functionalizations.…”

Section: Introductionmentioning

confidence: 99%

Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds

2020

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During the past decades, synthetic organic chemistry discovered that directing group assisted C−H activation is a key tool for the expedient and siteselective construction of C−C bonds. Among the various directing group strategies, bidentate directing groups are now recognized as one of the most efficient devices for the selective functionalization of certain positions due to fact that its metal center permits fine, tunable, and reversible coordination. The family of bidentate directing groups permit various types of assistance to be achieved, such as N,N-dentate, N,O-dentate, and N,S-dentate auxiliaries, which are categorized based on the coordination site. In this review, we broadly discuss various C− H bond functionalization reactions for the formation of C−C bonds with the aid of bidentate directing groups.

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Section: Introductionmentioning

confidence: 99%

Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds

2020

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“…In organic synthesis, C−H functionalization in the presence of transition metal catalysts has become one of the fundamental methods, and has had a massive impact on synthetic organic chemistry, medicinal chemistry, and material science [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 ]. In this context, cross dehydrogenative coupling (CDC) reactions have gained much interest in the last decade [ 9 , 10 , 11 , 12 , 13 , 14 , 15 ] among all types of C-H functionalization/activation reactions.…”

Section: Introductionmentioning

confidence: 99%

MnO2-Mediated Oxidative Cyclization of “Formal” Schiff’s Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines

et al. 2022

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A different type of MnO2-induced oxidative cyclization of dihydrotriazines has been developed. These dihydrotriazines are considered as a “formal” Schiff’s base. This method provided easy access to naphthofuro-fused triazine via the C-C/C-O oxidative coupling reaction. The reaction sequence comprised the nucleophilic addition of 2-naphthol or phenol to 1,2,4-triazine, followed by oxidative cyclization. The scope and limitations of this novel coupling reaction have been investigated. Further application of the synthesized compound has been demonstrated by synthesizing carbazole-substituted benzofuro-fused triazines. The scalability of the reaction was demonstrated at a 40 mmol load. The mechanistic study strongly suggests that this reaction proceeds through the formation of an O-coordinated manganese complex.

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“…We and other groups , have investigated Cp*Co III catalysts for C–H bond functionalization as an inexpensive alternative to Cp*Rh III catalysts after our first report in 2013 . Glorius and Ackermann independently reported Cp*Co III -catalyzed C–H allylation of indoles, pyrroles, and 2-phenylpyridines using preactivated allyl alcohol derivatives under mild conditions.…”

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confidence: 99%

Cp*Co^III-Catalyzed Dehydrative C–H Allylation of 6-Arylpurines and Aromatic Amides Using Allyl Alcohols in Fluorinated Alcohols

et al. 2016

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Cobalt-Catalyzed C-C Bond-Forming Reactions via Chelation-Assisted C-H Activation

Cited by 17 publications

References 60 publications

Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds

Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds

MnO2-Mediated Oxidative Cyclization of “Formal” Schiff’s Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines

Cp*Co^III-Catalyzed Dehydrative C–H Allylation of 6-Arylpurines and Aromatic Amides Using Allyl Alcohols in Fluorinated Alcohols

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Cobalt-Catalyzed C-C Bond-Forming Reactions via Chelation-Assisted C-H Activation

Cited by 17 publications

References 60 publications

Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds

Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds

MnO2-Mediated Oxidative Cyclization of “Formal” Schiff’s Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines

Cp*CoIII-Catalyzed Dehydrative C–H Allylation of 6-Arylpurines and Aromatic Amides Using Allyl Alcohols in Fluorinated Alcohols

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Cp*Co^III-Catalyzed Dehydrative C–H Allylation of 6-Arylpurines and Aromatic Amides Using Allyl Alcohols in Fluorinated Alcohols