The Reaction of Enamines with Aromatic Diazonium Salts

Crary, James W.; Quayle, Osborne R.; Lester, Chas. T.

doi:10.1021/ja01602a033

Cited by 16 publications

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“…(5) reported the addition of a variety of radicals to silyl enol ethers, leading to a-substituted ketones [eqn. (7)]. 17 On the other hand, a-arylation of ketones through the reaction of alkali metal enolates with aryl radicals has also been known as an SR,l reaction [eqn.…”

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Reaction of silyl enol ethers with arenediazonium salts. Part 1. α-Arylation of ketones

Sakakura¹,

Hara²,

Tanaka³

1994

J. Chem. Soc., Perkin Trans. 1

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m-Arylation of ketones is accomplished b y the use of arenediazonium salts as aryl-cation equivalents. The reaction of silyl enol ethers with arenediazonium tetrafluoroborates proceeds in the presence of palladium(0) catalysts and tetraphenylborate anion to give x-aryl ketones in moderate yields. Alternatively, silyl enol ethers smoothly react with arenediazonium tetrafluoroborates in pyridine even without palladium catalysts and tetraphenylborate anion, affording arylated ketones in good yields. A mechanism involving addition of an aryl radical t o a silyl enol ether is proposed for the latter process.

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“…( 12) is reasonable because the rate of radical addition to an olefin is accelerated when the resulting radical is benzylic; similar substituent effects were also observed for the reactions of eqns. (7) and (9). When R' in eqn.…”

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confidence: 99%

Reaction of silyl enol ethers with arenediazonium salts. Part 1. α-Arylation of ketones

Sakakura¹,

Hara²,

Tanaka³

1994

J. Chem. Soc., Perkin Trans. 1

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The Coupling of Diazonium Salts with Aliphatic Carbon Atoms

Parmerter

2011

Organic Reactions

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A diazonium salt will couple with an aliphatic compound containing an activated carbon‐hydrogen bond. This discussion is limited to those reactions in which both the nitrogen atoms of the diazonium salts are retained in the resulting molecule. The discussion is further limited by the exclusion of coupling reactions, which occur with the elimination of a group from an activated methinyl compound, the Japp‐Klingemann reaction. These reactions are discussed in Chapter 2. Much of the early work with coupling was prompted by the desire to determine whether the products were of the azo or hydrazonestructure. It is difficult to establish the structures in such cases where the tautomeric forms are possible. It is generally considered that the hydrazone is the stable form.

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Electrophilic Amination of Carbanions, Enolates, and Their Surrogates

Ciganek

2009

Organic Reactions

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This chapter deals with the formation of carbon‐nitrogen bonds by reaction of carbon nucleophiles with electrophilic aminating reagents. The former encompass aliphatic and aromatic carbanions, enolates and their surrogates such as enamines, enol esters, and enol ethers, as well as carbanions stabilized by cyano or sulfone groups or by phosphorus. A section entitled Reagents and Mechanisms lists the many aminating reagents available and discusses the mechanisms by which the more important ones react. Among the electrophiles discussed are halo amines, various hydroxylamine derivatives, oxaziridines, imines, oximes, diazonium salts, diazo compounds, azo compounds, and azides. The section on Scope and Limitations is organized by carbon nucleophiles and attempts to suggest the best reagents for each class. A number of electrophilic aminating reagents that have been omitted from the scope of this chapter are briefly discussed, with references to reviews, in the section on Comparison with Other Methods. Tables listing references to the preparation of the various aminating reagents are found in the section on Experimental Conditions. References to the conversion of non‐amine products into amines are also provided there. The literature is covered to the middle of 2007.

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The Reaction of Enamines with Aromatic Diazonium Salts

Cited by 16 publications

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Reaction of silyl enol ethers with arenediazonium salts. Part 1. α-Arylation of ketones

Reaction of silyl enol ethers with arenediazonium salts. Part 1. α-Arylation of ketones

The Coupling of Diazonium Salts with Aliphatic Carbon Atoms

Electrophilic Amination of Carbanions, Enolates, and Their Surrogates

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