Microwave-assisted benzyl-transfer reactions of commercially available 2-benzyloxy-1-methylpyridinium triflate.

Benzylation of alcohols and other substrates under thermal conditions translates smoothly from conventional heating into MW-assisted organic synthesis (MAOS). Reactions times are decreased from hours to minutes while good to excellent yields are maintained. MW heating should be considered for benzylation of high-value substrates using the title reagent.

Single-Phase Photo-Cross-Linkable Bioinspired Adhesive for Precise Control of Adhesion Strength.

A bioinspired, modular terpolymer adhesive, poly(N-methacryloyl-3,4-dihydroxyl-l-phenylalanine-co-9-(acryloyloxy)butyl anthracene-9-carboxylate-co-acrylic acid), has been synthesized containing three different functionalities: a photo-cross-linking segment, a wet interfacial adhesion segment, and a water-soluble segment. The synthesized adhesive polymer is the first example of a single-phase, photo-cross-linkable adhesive which does not require additional photoinitiator or other cross-linking agents. The terpolymer demonstrates strong adhesion when it swells in water and/or ethanol. The terpolymer is composed of three repeating units: N-methacryloyl-3,4-dihydroxyl-l-phenylalanine (MDOPA), which has been known to generate strong adhesion under wet conditions, poly(acrylic acid), which has been known to increase water solubility of polymers, and a photo-cross-linking segment consisting of an anthracene-based monomer used for enhancement of cohesion properties via UV irradiation (352 nm). A photomediated [4 + 4] cycloaddition reaction of anthracene results in the cross-linking of individual polymer chains after interfacial adhesion between substrates and adhesive polymers. Chemically, the covalent photo-cross-linking was confirmed by UV-vis, 1H NMR, and gel permeation chromatography (GPC). The cross-linking-fortified cohesion of the adhesive polymer network yields strengthened cohesion properties of the bulk material. The photoreaction was conveniently controlled via the duration of UV-irradiation. The adhesion properties of new adhesives were characterized by lap shear strength on transparent Mylar film and glasses after the adhesive was swollen in biologically friendly solvents including water and ethanol. The adhesion strength (J/m2) was enhanced by 850% under 352 nm UV-irradiation. Multiple application variables were tested to determine the optimal conditions, such as solvent, concentration, polymer composition, and substrate. The best adhesion properties were obtained from a 1:1 weight ratio of polymer:solvent in water on a Mylar film surface. As a single-phase system, the synthesized terpolymer is very convenient to use, and its adhesion strength can be easily modified by UV light. Additionally, the terpolymer's high water compatibility makes it ideally suited for application in the biomedical field.

Synthesis of the tricyclic core of aldingenin B by oxidative cyclo-ketalization of an alkyne-diol.

The preparation and selenium-mediated cyclo-ketalization of an alkyne-diol is described as a model study for the synthesis of aldingenin B. The oxidative cyclization is a simplifying transformation for aldingenin B, as it provides a convenient method for generating the tricylic core of the natural product from a functionalized cyclohexane.