Palladium catalyzed transfer of allylic groups

Atkins, Kenneth E.; Walker, W. E.; Manyik, Robert M.

doi:10.1016/s0040-4039(01)98599-5

Cited by 196 publications

(45 citation statements)

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“…[24] In 1970, Atkins et al disclosed the formation of C-N bonds in the reactions between diethylamine and allyl alcohol or but-2-ene-1,4-diol in the presence of Pd(acac) 2 / PPh 3 as the catalytic system and in the absence of solvent [Equations (5) and (6)]. [25] However, the teams of Bäckvall [26] and Mortreux [27] were unable to reproduce the allylation of diethylamine under such conditions [Equation (7)]. Furthermore, Bergbreiter et al obtained only a 5 % yield for the allylation of piperidine with allyl alcohol in the presence of a heterogeneous polystyrene-bound palladium catalyst at 100°C under neat conditions.…”

Section: -Catalyzed Allylations In the Absence Of Activatormentioning

confidence: 99%

Procedures for and Possible Mechanisms of Pd‐Catalyzed Allylations of Primary and Secondary Amines with Allylic Alcohols

Мuzart

2007

Eur J Org Chem

166

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This review describes the different Pd‐catalyzed methods that afford allylic amines from intermolecular reactions between allylic alcohols and amines and, with personal comments, the mechanisms that have been proposed. Allylic amines are an important class of compounds, while a wide structural variety of allylic alcohols are commercially available and are abundant in nature. The advantages of the use of allylic alcohols over that of their derivatives such as allylic esters or carbonates are the high atom efficiency and the formation only of water as the by‐product. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Section: -Catalyzed Allylations In the Absence Of Activatormentioning

confidence: 99%

Procedures for and Possible Mechanisms of Pd‐Catalyzed Allylations of Primary and Secondary Amines with Allylic Alcohols

Мuzart

2007

Eur J Org Chem

166

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“…22, No. 9,1990 tion to give the acetic acid salt of 5 (50°C, 0.3 mmHg). Acetic acid was removed by treating the CH2 Cl2 solution of the salt with aq.…”

Section: A Typical Procedures For the Reaction Ofla With Nn -Dimethylmentioning

confidence: 99%

“…le with piperazine resulted in recovering the starting materials, though allylic alcohol has been known to function as the substrates for the palladium catalyzed amination. 9 The molecular weight of the product polyamine was not high owing probably to the precipitation of the polymer during the reaction. The reaction in CHC1 3 , in which the polymer was soluble, was very slow.…”

Section: The Reaction Oflb With Nn'-ditosylethylene(or Trime Thylenementioning

confidence: 99%

“…22, No. 9,1990 amine or an acyclic secondary amine in the place of piperazine, cyclic oligomers were produced along with linear oligomers. The 1 H NMR spectrum of the reaction mixture of la with n-butylamine showed three peaks at i5 3.24, 3.15, and 2.89, which were assignable to methylene protons between the nitrogen atom and the C = C double bond.…”

mentioning

confidence: 99%

“…22, No. 9,1990 type reaction. 10 Accordingly, 8 is favorable for the oxidative addition at the less hindered vinylic carbon.…”

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confidence: 99%

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Polycondensation Catalyzed by Palladium Complex III. Syntheses of Linear Polyamines and Cyclic Oligoamines via π-Allyl Palladium Intermediates

Suzuki

Lim

Oguni

et al. 1990

Polym J

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ABSTRACT:A new polymerization reaction with a Pd (0) catalyst has been explored, in which polyamines (linear and cyclic) having amino groups in the main chains are produced. Two components of monomeric compounds are employed; the one is a bifunctional allylic compound and the other is amine. As the amine components, tosylated amines are employed, too, to produce the corresponding tosylated derivatives of polyamine. A kind of polycondensation proceeded via a n-allyl palladium intermediate. The monomer structure and the character of the catalyst influence the proportion between linear and cyclic products.KEY WORDS Polyamine / Cyclic Oligoamine / Polycondensation / Palladium Catalyst/ n-Allyl Palladium Complex/ It is very interesting to contemplate useful synthetic reactions from the viewpoint of polymer synthesis. Our attention has been directed to palladium catalyzed synthetic reactions which have actively been explored in these two decades. 1 Then, we have recently reported a novel polycondensation by using the Heck reaction 2 and a quite new type of ring-opening polymerization which proceeds via a n-allyl palladium complex. 3 This paper deals with a new polycondensation via a n-allyl palladium intermediate to produce polyamines having amino groups in the main chains, cyclic oligoamines, and their Ntosylated derivatives.Polymeric amines have actively been studied due to their characteristic properties and potentials of various applications. 4 As to the synthetic methods for polyamines, there have been several reports. 4 The ordinary method is the reaction between a dihalo compound and

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Allyl Alcohol and Monoallyl Derivatives

Nagato¹

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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The technology of introducing a new functional group to the double bond of allyl alcohol was developed in the mid‐1980s. Allyl alcohol is accordingly used as an intermediate compound for synthesizing raw materials such as epichlorohydrin and 1,4‐butanediol, and this development is bringing about expansion of the range of uses of allyl alcohol. Allyl alcohol is a colorless liquid having a pungent odor; its vapor may cause severe irritation and injury to eyes, nose, throat, and lungs. It is also corrosive. Allyl alcohol is freely miscible with water and miscible with many polar organic solvents and aromatic hydrocarbons. It forms an azeotropic mixture with water and a ternary azeotropic mixture with water and organic solvents. Hydroformylation of allyl alcohol is a synthetic route for producing 1,4‐butanediol, a raw material for poly(butylene terephthalate), an engineering plastic. The \documentclass{article}\usepackage{amssymb}\pagestyle{empty}\begin{document}${{\rm{C}}{\raise1pt\hbox{$\Relbar \kern-4pt{\Relbar}$}}{\rm{C}}}$\end{document} double bond of allyl alcohol undergoes epoxidation by peroxide, yielding glycidol, applied in manufacturing glycidol as an intermediate for industrial production of glycerol. There are two processes for industrial production of allyl alcohol being used industrially at present: isomerization of propylene oxide, and a new process developed by Showa Denko K.K. The monoallyl derivative allyl chloride (AC) is a transparent, mobile, and irritative liquid produced by chlorination of propylene at high temperature. It is used mostly as an intermediate compound for producing epichlorohydrin. Allyl acetate is produced mostly for manufacturing allyl alcohol. Allyl methacrylate (AMA) is used mostly as a raw material for silane coupling agents. Allyl glycidyl ether is used mainly as a raw material for silane coupling agents and epichlorohydrin rubber. Dimethylallylamine is used in the production of insecticides and pesticides. Most allyl compounds are toxic and many are irritants. Precautions should be taken at all times to ensure safe handling.

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Palladium catalyzed transfer of allylic groups

Cited by 196 publications

References 0 publications

Procedures for and Possible Mechanisms of Pd‐Catalyzed Allylations of Primary and Secondary Amines with Allylic Alcohols

Procedures for and Possible Mechanisms of Pd‐Catalyzed Allylations of Primary and Secondary Amines with Allylic Alcohols

Polycondensation Catalyzed by Palladium Complex III. Syntheses of Linear Polyamines and Cyclic Oligoamines via π-Allyl Palladium Intermediates

Allyl Alcohol and Monoallyl Derivatives

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