Reduction of Aryl Mesylates Catalyzed by Nickel Complexes

Sasaki, Kenji; Kubo, Tatsuya; Sakai, Mutsuji; Kuroda, Yasuhisa

doi:10.1246/cl.1997.617

Cited by 20 publications

(12 citation statements)

References 7 publications

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“…Further optimization of the reaction conditions provided access aryl mesylates as available substrates 403. While dppp in methanol was effective for reduction of tosylates, dppb showed better reactivity for mesylates in methanol/DMF (30%) mixture.…”

Section: Nickel-catalyzed Reactions Of Aryl and Vinyl Sulfonates Amentioning

confidence: 99%

Nickel-Catalyzed Cross-Couplings Involving Carbon−Oxygen Bonds

et al. 2010

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Section: Nickel-catalyzed Reactions Of Aryl and Vinyl Sulfonates Amentioning

confidence: 99%

Nickel-Catalyzed Cross-Couplings Involving Carbon−Oxygen Bonds

et al. 2010

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“…For example, in 1991, Sasaki’s group documented a very early example of reduction of aryl triflates catalyzed by NiBr 2 (PPh 3 ) 2 /dppp with Zn dust as the reductant in methanol . Six years later, in 1997, the same group achieved the reduction of aryl mesylates via changing the dppp ligand to dppb . In 1992, Tada’s group reported a nice example of reduction of aryl tosylates via a NiCl 2 –NaBH 4 catalytic system; however, NiCl 2 was utilized in a stoichiometric amount .…”

Section: Phenol C–o Functionalizationsmentioning

confidence: 98%

“…122 Six years later, in 1997, the same group achieved the reduction of aryl mesylates via changing the dppp ligand to dppb. 123 In 1992, Tada's group reported a nice example of reduction of aryl tosylates via a NiCl 2 −NaBH 4 catalytic system; however, NiCl 2 was utilized in a stoichiometric amount. 124 Later, in 1994, Tı ́maŕ's group employed Raney Ni as the catalyst with H 2 as the reductant to realize the reduction of aryl tosylates and mesylates.…”

Section: C−h Bond Formation (Hydrogenolysis Of C−o)mentioning

confidence: 99%

Transformations of Less-Activated Phenols and Phenol Derivatives via C–O Cleavage

2020

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Employing phenols and phenol derivatives as electrophiles for cross-coupling reactions has numerous advantages over commonly used aryl halides in terms of environmental-friendliness and sustainability. In the early stage of discovering such transformations, most efforts have been devoted to utilizing highly activated sulfonate types of phenol derivatives (e.g., OTf, OTs, etc.), which have similar reactivities to the corresponding aryl halides. However, a continuing scientific challenge is how to achieve the direct C–O functionalizations of relatively less-activated phenol derivatives more efficiently. In this review, we will focus on the recent updates on the C–O functionalizations of less-activated phenol derivatives, from aryl carboxylates (e.g., pivalates, acetates, etc.), aryl carbamates and carbonates, to aryl ethers (anisoles, diaryl ethers, aryl pyridyl ethers, aryl silyl ethers), to phenolate salts, and ultimately to simply unprotected phenols, sorted by the types of bond formations. Both transition-metal-catalyzed and transition-metal-free protocols will be covered and discussed in detail. Instead, the C–O functionalizations of aryl sulfonates will not be covered extensively unless they are closely related, due to their high reactivity. Since aryl ethers and phenols represent the main linkages or units in lignin biomass, the successes of such transformations will potentially make major contributions to the direct lignin biomass upgrading and depolymerization.

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“…[23] Later, the use of Raney nickel as a catalyst for the transfer hydrogenation of aryl and vinyl perfluoroalkyl sulfonates was compared with palladium and PtO 2 catalysts, and a very high potential for deoxygenation by using this catalyst was found. Sasaki et al showed the deoxygenation of aryl triflates [25] and mesylates [26] with NiBr 2 (PPh 3 ) 3 /dppp as the catalyst, zinc as the reductant, and methanol as the hydrogen donor. Sasaki et al showed the deoxygenation of aryl triflates [25] and mesylates [26] with NiBr 2 (PPh 3 ) 3 /dppp as the catalyst, zinc as the reductant, and methanol as the hydrogen donor.…”

Section: Nickel-catalyzed Deoxygenationsmentioning

confidence: 99%

Reductive Deoxygenation of Alcohols: Catalytic Methods Beyond Barton–McCombie Deoxygenation

2013

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Deoxygenation is an extensively studied field in organic chemistry, and over the last decades many methods such as the Barton–McCombie deoxygenation reaction or deoxygenation with alkali metals in liquid ammonia have been established. Within this microreview, we discuss different strategies for the chemoselective catalytic deoxygenation of alcohols with special attention to their scope and limitations. The deoxygenation of derivatives of alcohols and their direct deoxygenation as step‐economic alternative are covered with current examples. Catalytic methods can serve as convenient and economic alternatives for established methods in the reduction of carbon–oxygen single bonds.

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Reduction of Aryl Mesylates Catalyzed by Nickel Complexes

Abstract: Aryl mesylates were found to be deoxygenatively reduced into the corresponding aromatic hydrocarbons by using nickel(0)-dppb/PPh3 catalyst with zinc powder and an alcohol as a hydrogen donor.

Cited by 20 publications

References 7 publications

Nickel-Catalyzed Cross-Couplings Involving Carbon−Oxygen Bonds

Nickel-Catalyzed Cross-Couplings Involving Carbon−Oxygen Bonds

Transformations of Less-Activated Phenols and Phenol Derivatives via C–O Cleavage

Reductive Deoxygenation of Alcohols: Catalytic Methods Beyond Barton–McCombie Deoxygenation

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