Aryl Allylic Alcohols Research Articles

Synthesis of branched and linear aryl allylic alcohols: C[sbnd]H bond allylation of 2-aryl-3H-indoles with vinyl cyclic carbonates

Presented herein is an effective synthesis of branched and linear allyl arenes based on the reactions of 2-aryl-3H-indoles with 5-methylene-1,3-dioxan-2-one or 4-vinyl-1,3-dioxolan-2-one. Mechanistically, the reactions are initiated by Rh(III)-catalyzed aryl C(sp2)–H bond activation/cyclometallation followed by vinyl coordination/migratory insertion and β–O elimination through release of CO2 as the only by-product. By using this newly developed protocol, a group of 2-aryl-3H-indole derivatives bearing the substructure of either branched or linear allylic alcohol were obtained in good efficiency. Notably, the linear allylic alcohols were obtained with excellent E/Z selectivity when unsubstituted vinyl-1,3-dioxolan-2-one was used as the allyl surrogate. With advantages such as easily available starting materials, mild and redox-neutral reaction conditions, good compatibility with a broad range of functional groups, benign solvent and divergent products, this protocol is expected to be used in the synthesis of indole-based functional molecules.

Photoredox/Nickel Dual Catalysis-Enabled Modular Synthesis of Arylallyl Alcohols with Acetylene as the Two-Carbon Synthon

Photoredox/Nickel Dual Catalysis-Enabled Modular Synthesis of Arylallyl Alcohols with Acetylene as the Two-Carbon Synthon

Ni-Catalyzed Allylic Dearomatization Reaction of β-Naphthols with Allylic Alcohols.

Ni-catalyzed intermolecular allylic dearomatization reaction of β-naphthols with allylic alcohols was achieved. By utilizing Ni(cod)2 as a catalyst precursor, DPEphos as a ligand and 4 Å molecular sieves as additives, the dearomatization reaction of β-naphthols with aryl allylic alcohols proceeded smoothly under mild conditions, affording the desired β-naphthalenone products bearing a quaternary carbon center in moderate to good yields with excellent linear selectivity.

Boron‐Catalyzed C−C Functionalization of Allyl Alcohols

AbstractTris(pentafluorophenyl)borane‐catalyzed C−C bond functionalization of arylallyl alcohols using donor‐acceptor carbenes is presented. The allylic hydroxyl group is found to assist the product formation by neighboring group participation providing a clue towards mechanistic understanding. This method can also be employed to effect homologation of allyl alcohols to homoallyl alcohols. Overall, this metal‐free transformation presents a novel disconnection strategy towards carbon‐carbon bond scission and formation.magnified image

Ruthenium-catalyzed synthesis of arylethyl 1,3,5-triazines from arylallyl alcohols and biguanides.

An efficient ruthenium-catalyzed synthesis of alkyl-1,3,5-triazies from arylallyl alcohols and biguanides has been developed. The reaction occurred in moderate to good yields and tolerated heterocyclic or aryl allyl alcohols containing functionalities such as alkanes, ethers, and halogens. The reaction proceeds through a one-pot sequence of transfer hydrogenation and condensation steps.

Gold-Catalyzed [2,3]-Sigmatropic Rearrangement: Reaction of Aryl Allyl Alcohols with Diazo Compounds.

A gold-catalyzed [2,3]-sigmatropic rearrangement reaction has been developed. The intermolecular rearrangement occurs between in situ generated donor-acceptor gold-carbenes and cinnamyl alcohols via tandem oxonium ylide formation. The desired rearranged product has been accomplished selectively over more conventional O-H insertion, cyclopropanation, cycloaddition, and C-H functionalization products under mild, open-air conditions. The scope of the work has been illustrated by synthesizing a new class of substrates that can be used for constructing complex molecular targets.

Palladium-catalyzed synthesis of quinolines from allyl alcohols and anilines

A process for quinoline synthesis through palladium-catalyzed oxidative cyclization of aryl allyl alcohols and anilines is described.

ChemInform Abstract: Visible Light‐Mediated Arylalkylation of Allylic Alcohols Through Concomitant 1,2‐Aryl Migration.

AbstractThe title reaction provides the synthesis of α‐aryl‐β‐alkylated ketones via 1,2‐aryl migration from aryl allylic alcohols.

One-Pot Synthesis of Allylic Sulfones, Ketosulfones, and Triflyl Allylic Alcohols from Domino Reactions of Allylic Alcohols with Sulfinic Acid under Metal-Free Conditions.

A metal-free tandem procedure by using a sulfonylation reaction of aryl allylic alcohols followed by an iodobenzenediacetate (PIDA)-promoted oxidative functionalization has been established. Allylic sulfones, γ-ketosulfones, and triflyl allylic alcohols have been constructed in a single operation. The methodology incorporates the sulfonyl (both aryl and triflyl) functionality with a simple work-up procedure.

Tandem Oxidation/Halogenation of Aryl Allylic Alcohols under Moffatt−Swern Conditions

Aryl allylic alcohols are converted to halogenated unsaturated ketones or allylic halides using excess Moffatt-Swern reagent. Electron-poor aromatic rings favor formation of the halogenated ketone, while electron-donating substituents in the ortho or para positions favor formation of the allylic halide. The oxidation/halogenation reaction performs well with both oxalyl chloride and oxalyl bromide, providing access to the corresponding chlorides or bromides, respectively.

ChemInform Abstract: ARYLALLYL CATIONS AND THEIR STEREOSPECIFIC CYCLIZATION TO BICYCLIC TRIENYLIC CATIONS

AbstractEine Reihe von Arylallylalkoholen (I), (IV) bzw. (VII) wird dargestellt [a) aus entsprechenden aromatischen Aldehyden und Li‐alkenen bzw. b) aus entsprechenden Li‐arenen und Croton‐ bzw. Tiglinaldehyd; meist gute Ausbeuten].

Consanguineous syntheses of polymethyl-substituted 1H-, 3aH-, and 5H-indenes from arylallyl alcohols

Consanguineous syntheses of polymethyl-substituted 1H-, 3aH-, and 5H-indenes from arylallyl alcohols

Arylallyl cations and their stereospecific cyclization to bicyclic trienylic cations

A series of arylallyl alcohols, where aryl = 2,6-dimethylphenyl, mesityl, duryl, or pentamethylphenyl, was prepared. On addition to strong acid, these generate arylallyl cations. In some cases these allyl cations are observable and were characterized as insitu solution species by nmr spectroscopy. In other cases, an immediate cyclization takes place, leading stereospecifically to a series of bicyclic trienyl cations, which were also thoroughly characterized. The stereochemistry of this cyclization reaction, which was initially expected to follow the "rules" for electrocyclic ring closures, was probed in some detail. It is tentatively concluded that the stereochemistry in the products is not that expected from a conrotatory ring closure. Two diarylmethyl cations were also prepared. However, these did not cyclize.