Oxidation of alcohols by transition metal complexes part V. Selective catalytic monoalkylation of arylacetonitriles by alcohols

Grigg, Ronald; Mitchell, T. R. B.; Sutthivaiyakit, Somyote; Tongpenyai, N.

doi:10.1016/s0040-4039(01)82078-5

Cited by 121 publications

(66 citation statements)

References 8 publications

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“…[15] However, methods that utilize methanol as an alkylating reagent with C–C bond formation (reported on PhCH 2 CN[2e, 16]) or as a substrate for formal C–H functionalization (such as the work by Krische et al[17]) are extremely rare and represent an important area in need of development.…”

mentioning

confidence: 99%

Rhodium‐Catalyzed Ketone Methylation Using Methanol Under Mild Conditions: Formation of α‐Branched Products

et al. 2013

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The rhodium-catalyzed methylation of ketones has been accomplished using methanol as the methylating agent and the hydrogen-borrowing method. The sequence is notable for the relatively low temperatures that are required and for the ability of the reaction system to form α-branched products with ease. Doubly alkylated ketones can be prepared from methyl ketones and two different alcohols by using a sequential one-pot iridium- and rhodium-catalyzed process.

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confidence: 99%

Rhodium‐Catalyzed Ketone Methylation Using Methanol Under Mild Conditions: Formation of α‐Branched Products

et al. 2013

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“…A wide variety of arylacetonitriles efficiently reacted with 8a, affording the α-ethylated nitriles in excellent yields without the formation of dialkylated products (entries 1-6). A 20 mmol scale reaction of 7a with 8a afforded 9a in 82% yield with a high TOF of 14 h -1 and a high TON of 412, which are considerably higher than those of a previously reported homogeneous Ru catalyst combined with the stoichiometric amount of Na 2 CO 3 (TOF, 0.77 h -1 ; TON, 18) [41]. The α-ethylation of a sterically hindered 1naphthylacetonitrile (7e) proceeded successfully to form 2-(1-naphthyl)-butyronitrile in high yield (9e).…”

Section: -2-2 Synthesis Of α-Alkylated Nitriles From Nitriles and Amentioning

confidence: 63%

Design of Ruthenium Catalysts Bound to Inorganic Crystalline Materials for Environmentally-Benign Organic Synthesis

Ebitani

Mizugaki²,

Mori³

et al. 2006

COC

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This article reviews a novel approach to design heterogeneous Ru catalysts using hydroxyapatites and hydrotalcites, and their excellent catalytic performances for aerobic alcohol oxidations, carbon-carbon bond formations, and one-pot syntheses. The catalytic systems using the above heterogeneous Ru catalysts offer significant benefits in achieving simple and clean organic syntheses. Furthermore, the present preparation method for the immobilization of metal species is much simpler than previous synthetic methods of the solid-supported transition metal catalysts, which can allow a strong protocol to create various nanostructured and functionalized heterogeneous metal catalysts. R 1 , R 2 = H, alkyl, aryl 242

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“…In 1981, Grigg and coworkers reported a ruthenium-catalysed a-alkylation of nitriles by alcohols. [58] More recently they have reported an improved alkylation of nitriles using [Cp*IrCl 2 ] 2 , allowing the mono-alkylation of arylacetonitriles with a wide range of aromatic, heteroaromatic and aliphatic alcohols. Alkylation of bis-and tris-primary alcohols also proceeded efficiently.…”

Section: à C Bond Formation From Alcoholsmentioning

confidence: 99%

Borrowing Hydrogen in the Activation of Alcohols

2007

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Alcohols can be temporarily converted into carbonyl compounds by the metal-catalysed removal of hydrogen. The carbonyl compounds are reactive in a wider range of transformations than the precursor alcohols and can react in situ to give imines, alkenes, and a-functionalised carbonyl compounds. The metal catalyst, which had borrowed the hydrogen, then returns it to the transformed carbonyl compound, leading to an overall process in which alcohols can be converted into amines, compounds containing C À C bonds and b-functionalised alcohols.

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Oxidation of alcohols by transition metal complexes part V. Selective catalytic monoalkylation of arylacetonitriles by alcohols

Cited by 121 publications

References 8 publications

Rhodium‐Catalyzed Ketone Methylation Using Methanol Under Mild Conditions: Formation of α‐Branched Products

Rhodium‐Catalyzed Ketone Methylation Using Methanol Under Mild Conditions: Formation of α‐Branched Products

Design of Ruthenium Catalysts Bound to Inorganic Crystalline Materials for Environmentally-Benign Organic Synthesis

Borrowing Hydrogen in the Activation of Alcohols

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