REDUCTION OF ORGANIC COMPOUNDS WITH LOW-VALENT NIOBIUM (NbCl5/NaAlH4)

Sato, Mitsuyoshi; Oshima, Koichiro

doi:10.1246/cl.1982.157

Cited by 47 publications

(14 citation statements)

References 13 publications

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“…o ‐Aryl‐ and o ‐alkenyltrifluorotoluenes afforded fluorene and indene derivatives in good yields (Scheme ). In contrast to the chemistry of Nb III and Nb V species, the chemistry of Nb 0 species is still underdeveloped 18. We also describe new reactions of the Nb 0 species.…”

Section: Introductionmentioning

confidence: 99%

CC Coupling Reactions of Superstrong CF₃ Groups with C(sp²)–H Bonds: Reactivity and Synthetic Utility of Zero‐Valent Niobium Catalyst

Fuchibe

Mitomi

Suzuki

et al. 2008

Chemistry An Asian Journal

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It was found that zero-valent niobium is an efficient catalyst for the intramolecular C-C coupling reactions of o-aryl and o-alkenyl alpha,alpha,alpha-trifluorotoluene derivatives. The superstrong C-F bonds of CF3 groups and neighboring C(sp2)-H bonds were doubly activated, and fluorenes and indenes were obtained in good yields. The niobium fluorocarbenoid species is proposed to be the key intermediate.

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Section: Introductionmentioning

confidence: 99%

CC Coupling Reactions of Superstrong CF₃ Groups with C(sp²)–H Bonds: Reactivity and Synthetic Utility of Zero‐Valent Niobium Catalyst

Fuchibe

Mitomi

Suzuki

et al. 2008

Chemistry An Asian Journal

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“…The conversion rate improved dramatically when sodium aluminum hydride was used, giving 2 c and 3 in yields of 27 % and 46 %, respectively (Table 1, entry 2; 30 mol % niobium(V) chloride) 14. 15 In contrast, alkoxy‐substituted aluminum hydride reagents were unreactive, resulting in the recovery of starting material 1 c (Table 1, entries 3 and 4) even when an equimolar amount of niobium(V) chloride was used 16…”

Section: Methodsmentioning

confidence: 99%

Expedient Synthesis of N‐Fused Indoles: A CF Activation and CH Insertion Approach

et al. 2009

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“…Later Sato and Oshima reported that a reagent derived from NbCl 5 and NaAlH 4 dimerizes carbonyl compounds and alcohols into deoxygenated coupling products (Scheme 4). 15 Reactions of allylic and benzylic alcohols gave 54-90% yields of dimers. Regioisomeric mixtures were observed with unsymmetrical allylic alcohols such as 4-methyl-3penten-2-ol and cyclohexenylmethanol.…”

Section: Scheme 3 Reductive Coupling Of Alcohols With Ticl 3 -Lialhmentioning

confidence: 99%

Deoxygenative Transition-Metal-Promoted Reductive Coupling and Cross-Coupling of Alcohols and Epoxides

Bandari¹,

Nicholas²

2020

Synthesis

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The prospective utilization of abundant, CO2-neutral, renewable feedstocks is driving the discovery and development of new reactions that refunctionalize oxygen-rich substrates such as alcohols and polyols through C–O bond activation. In this review, we highlight the development of transition-metal-promoted reactions of renewable alcohols and epoxides that result in carbon–carbon bond-formation. These include reductive self-coupling reactions and cross-coupling reactions of alcohols with alkenes and arene derivatives. Early approaches to reductive couplings employed stoichiometric amounts of low-valent transition-metal reagents to form the corresponding hydrocarbon dimers. More recently, the use of redox-active transition-metal catalysts together with a reductant has enhanced the practical applications and scope of the reductive coupling of alcohols. Inclusion of other reaction partners with alcohols such as unsaturated hydrocarbons and main-group organometallics has further expanded the diversity of carbon skeletons accessible and the potential for applications in chemical synthesis. Catalytic reductive coupling and cross-coupling reactions of epoxides are also highlighted. Mechanistic insights into the means of C–O activation and C–C bond formation, where available, are also highlighted.1 Introduction2 Stoichiometric Reductive Coupling of Alcohols3 Catalytic Reductive Coupling of Alcohols3.1 Heterogeneous Catalysis3.2 Homogeneous Catalysis4 Reductive Cross-Coupling of Alcohols4.1 Reductive Alkylation4.2 Reductive Addition to Olefins5 Epoxide Reductive Coupling Reactions6 Conclusions and Future Directions

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REDUCTION OF ORGANIC COMPOUNDS WITH LOW-VALENT NIOBIUM (NbCl5/NaAlH4)

Abstract: Carbonyl compounds have been deoxygenatively dimerized to alkenes with the title reagent. Deoxygenation of epoxides to alkenes, reductive coupling of allylic and benzylic alcohols to hydrocarbons, and reduction of alkynes to alkenes are also described.

Cited by 47 publications

References 13 publications

CC Coupling Reactions of Superstrong CF₃ Groups with C(sp²)–H Bonds: Reactivity and Synthetic Utility of Zero‐Valent Niobium Catalyst

CC Coupling Reactions of Superstrong CF₃ Groups with C(sp²)–H Bonds: Reactivity and Synthetic Utility of Zero‐Valent Niobium Catalyst

Expedient Synthesis of N‐Fused Indoles: A CF Activation and CH Insertion Approach

Deoxygenative Transition-Metal-Promoted Reductive Coupling and Cross-Coupling of Alcohols and Epoxides

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REDUCTION OF ORGANIC COMPOUNDS WITH LOW-VALENT NIOBIUM (NbCl5/NaAlH4)

Abstract: Carbonyl compounds have been deoxygenatively dimerized to alkenes with the title reagent. Deoxygenation of epoxides to alkenes, reductive coupling of allylic and benzylic alcohols to hydrocarbons, and reduction of alkynes to alkenes are also described.

Cited by 47 publications

References 13 publications

CC Coupling Reactions of Superstrong CF3 Groups with C(sp2)–H Bonds: Reactivity and Synthetic Utility of Zero‐Valent Niobium Catalyst

CC Coupling Reactions of Superstrong CF3 Groups with C(sp2)–H Bonds: Reactivity and Synthetic Utility of Zero‐Valent Niobium Catalyst

Expedient Synthesis of N‐Fused Indoles: A CF Activation and CH Insertion Approach

Deoxygenative Transition-Metal-Promoted Reductive Coupling and Cross-Coupling of Alcohols and Epoxides

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CC Coupling Reactions of Superstrong CF₃ Groups with C(sp²)–H Bonds: Reactivity and Synthetic Utility of Zero‐Valent Niobium Catalyst

CC Coupling Reactions of Superstrong CF₃ Groups with C(sp²)–H Bonds: Reactivity and Synthetic Utility of Zero‐Valent Niobium Catalyst