Monoallylation Products Research Articles

B/Pd Synergistic Catalysis for the Decarboxylative Allylation of 2-(2-Azaaryl)acetic Acids.

We describe an allylation reaction between 2-(2-azaaryl)acetic acids and allylic electrophiles catalyzed synergistically by a dual system consisting of borinic acid and a Pd complex under mild conditions. The decarboxylative allylation proceeds via a boron-bound enamine intermediate, which then interacts with a π-allylpalladium intermediate from the allylic electrophile. High yields of diallylation products highlight the method's efficiency. Intriguingly, when using 2-(2-pyridyl)acetic acid with a C3 substituent on the pyridyl ring, the reaction exclusively yields monoallylation products.

Ruthenium(ii)-catalysed direct synthesis of mono-allylation products of 1,3-diketones from cinnamyl alcohols

The complex, [Ru(p-cymene)(dppe)Cl]PF6·C7H8 is an efficient catalyst for the direct carbon–carbon bond formation reactions to form enantio- and regioselective mono-allylation products of diketones by cinnamyl alcohol with high yield.

Cobalt‐Catalyzed C—H Allylation of Arenes with Allylic Amines

Main observation and conclusion[Cp*Co(CO)I2] effectively catalyzes pyridyl‐directed C—H allylation of arenes with allylic amines in the presence of AgOAc and CF3COOAg. The reaction features ortho‐position monoallylation of 2‐pyridylarenes, giving the allylated arenes in moderate to high yields. A range of functional groups including OMe, Me, Ph, F, Cl, Br, CF3, C(O)Me, COOEt, and COOH groups are tolerated. Pyrimidyl‐directed C—H allylation of arenes were also performed under the same conditions. Reaction of 2‐phenylpyrimidine, 2‐(4‐methoxyphenyl)pyrimidine, and 2‐(3‐fluorophenyl)pyrimidine leads to a mixture of ortho‐position mono‐ and bisallylation products. Reaction of other 2‐(substituted aryl)pyrimidines resulted in ortho‐position monoallylation products.

ChemInform Abstract: Dual Platinum and Pyrrolidine Catalysis in the Direct Alkylation of Allylic Alcohols: Selective Synthesis of Monoallylation Products.

AbstractThe title reaction proceeds in a highly selective manner furnishing monoallylation products for a broad substrate scope.

Dual Platinum and Pyrrolidine Catalysis in the Direct Alkylation of Allylic Alcohols: Selective Synthesis of Monoallylation Products

AbstractA dual platinum‐ and pyrrolidine‐catalyzed direct allylic alkylation of allylic alcohols with various active methylene compounds to produce products with high monoallylation selectivity was developed. The use of pyrrolidine and acetic acid was essential, not only for preventing undesirable side reactions, but also for obtaining high monoallylation selectivity.

Dual Platinum and Pyrrolidine Catalysis in the Direct Alkylation of Allylic Alcohols: Selective Synthesis of Monoallylation Products

A dual platinum- and pyrrolidine-catalyzed direct allylic alkylation of allylic alcohols with various active methylene compounds to produce products with high monoallylation selectivity was developed. The use of pyrrolidine and acetic acid was essential, not only for preventing undesirable side reactions, but also for obtaining high monoallylation selectivity.

Intermolecular Amination of Allyl Alcohols with Sulfamates: Effective Utilization of Mercuric Catalyst

AbstractHerein, we describe the intermolecular amination of allyl alcohols with sulfamates, which have been underutilized as nitrogen nucleophiles for allylic amination. Methyl sulfamate is a good nucleophile in the presence of mercuric triflate and efficiently generates monoallylation products in excellent yield at room temperature. Furthermore, the solid‐supported mercuric catalyst silaphenyl mercuric triflate also showed remarkable catalytic activity for the allylic amination.

Deacylative allylation of nitroalkanes: unsymmetric bisallylation by a three-component coupling.

Deacylative allylation of nitroalkanes: unsymmetric bisallylation by a three-component coupling.

Conjugate allylation reactions of alkylidene malononitriles mediated by NHC-ligated palladium catalysts

Conjugate allylation of malononitriles is reported using catalytic N-heterocyclic carbene-ligated palladium complexes. This conjugate allylation reaction yields a variety of monoallylated products. These results contrast the bis-allylation of malononitriles using other palladium-based catalysts. This reaction tolerates a wide variety of functional groups including aryl groups, heteroaromatics, and aliphatic substituents to provide the desired products in good to excellent yields. Derivativation of the monoallylation products to form a triamino pyrimidine is demonstrated.

Direct Use of Allylic Alcohols for Platinum-Catalyzed Monoallylation of Amines

A new direct catalytic amination of allylic alcohols promoted by the combination of platinum and a large bite-angle ligand DPEphos was developed in which the allylic alcohol was effectively converted to a pi-allylplatinum intermediate without the use of an activating reagent. The use of the DPEphos ligand was essential for obtaining high catalyst activity and high monoallylation selectivity of primary amines, allowing the formation of a variety of monoallylation products in good to excellent yield.

Effect of Lithium Chloride on Allylation of Zirconacyclopentadienes.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Effect of lithium chloride on allylation of zirconacyclopentadienes

The effects of lithium chloride on the allylation of zirconacyclopentadienes with allylic halides in the presence of CuCl have been studied. It is found that mono-allylation products are formed predominantly in the absence of lithium chloride, while the presence of lithium chloride leads to the formation of di-allylation products.

Direct Palladium(0)‐Catalyzed Amination of Allylic Alcohols with Aminonaphthalenes.

AbstractFor Abstract see ChemInform Abstract in Full Text.

(π‐Allyl)palladium Complexes Bearing Diphosphinidenecyclobutene Ligands (DPCB): Highly Active Catalysts for Direct Conversion of Allylic Alcohols.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Direct palladium(0)-catalyzed amination of allylic alcohols with aminonaphthalenes

The direct activation of CO bonds in allylic alcohols by palladium complexes has been accelerated by carrying out the reactions in the presence of titanium reagents. The palladium-catalyzed amination of allylic alcohols using aminonaphthalenes gave N-allylic naphthylamines in good yields. The monoallylation products are formed in the main.

(Pi-allyl)palladium complexes bearing diphosphinidenecyclobutene ligands (DPCB): highly active catalysts for direct conversion of allylic alcohols.

The (pi-allyl)palladium complex bearing an sp2-hybridized phosphorus ligand (DPCB-OMe: 1,2-bis(4-methoxyphenyl)-3,4-bis[(2,4,6-tri-tert-butylphenyl)phosphinidene]cyclobutene) efficiently catalyzes direct conversion of allylic alcohols in the absence of activating agents of alcohols such as Lewis acids. N-Allylation of aniline proceeds at room temperature to afford monoallylated anilines in 90-97% yields. C-Allylation of active methylene compounds is also successful at 50 degrees C using a catalytic amount of pyridine as a base, giving monoallylation products in 85-95% yields. The catalytic mechanism involving hydrido- and (pi-allyl)palladium intermediates has been proposed on the basis of stoichiometric examinations using model compounds of presumed intermediates.

ChemInform Abstract: A CONVENIENT ALLYLATION OF ORTHO‐QUINONES. AN EXTENSION ON THE UTILITY OF ALLYLTIN REAGENTS

AbstractDie Naphthochinone (I) reagieren mit den Tributylallylzinnverbindungen (II) zu den 4‐Allyldihydroxynaphthalinen (III), die Benzochinone (IV) zu den Allylbrenzkatechinen (V) in sehr guten Ausbeuten.

A CONVENIENT ALLYLATION OF ORTHO-QUINONES. AN EXTENSION ON THE UTILITY OF ALLYLTIN REAGENTS

Abstract Lewis acid catalyzed allylation of 1,2-naphthoquinones and o-benzoquinones with allyltributyltins gave monoallylation products in reasonable to high yields.