55609-63-7

Upstream product

• 941-69-5 N-phenyl-maleimide 
• 770-09-2 benzyltrimethylsilane 
• 108-88-3 toluene 
• 451-40-1 phenyl benzyl ketone 
• 23215-60-3 2-benzyl-2-phenylbenzothiazoline 
• 103-82-2 phenylacetic acid 
• 201230-82-2 carbon monoxide 
• 10147-11-2 propargyl benzene 
• 62-53-3 aniline 
• 36092-42-9 2-benzylsuccinic acid 

Relevant academic research and scientific papers

Metal-free desilylative C-C bond formation by visible-light photoredox catalysis

A newly developed methodology for the use of organosilanes as radical precursors under metal-free and visible-light conditions is presented. The strong oxidant character of the 9-mesityl-10-methylacridinium salt in its excited state enables the transforma

Benzothiazolines as radical transfer reagents: Hydroalkylation and hydroacylation of alkenes by radical generation under photoirradiation conditions

Novel radical transfer reagents under photoirradiation conditions were developed by the use of benzothiazoline derivatives. These reagents enabled both hydroalkylation and hydroacylation of alkenes under neutral conditions at ambient temperature without a

Smooth Photocatalyzed Benzylation of Electrophilic Olefins via Decarboxylation of Arylacetic Acids

Arylacetic acids were used as sources of benzyl radicals under tetrabutylammonium decatungstate photocatalyzed conditions for the benzylation of electron-poor olefins. The reaction proceeds smoothly in a mixed aqueous medium (MeCN/H2O 2/1) in t

Palladium-catalyzed aminocarbonylation of alkynes to succinimides

Succinimide derivatives are useful building blocks for the synthesis of natural products and drugs. We describe an efficient route to succinimide derivatives comprising Pd(xantphos)Cl2-catalyzed aminocarbonylation of alkynes with aromatic or aliphatic amines in the presence of p-TsOH. The utility of this route is demonstrated with the synthesis of a large number of succinimide compounds including an important photochromic molecule.

Titania-promoted carboxylic acid alkylations of alkenes and cascade addition-cyclizations

Photochemical reactions employing TiO2 and carboxylic acids under dry anaerobic conditions led to several types of C-C bond-forming processes with electron-deficient alkenes. The efficiency of alkylation varied appreciably with substituents in the carboxylic acids. The reactions of aryloxyacetic acids with maleimides resulted in a cascade process in which a pyrrolochromene derivative accompanied the alkylated succinimide. The selectivity for one or other of these products could be tuned to some extent by employing the photoredox catalyst under different conditions. Aryloxyacetic acids adapted for intramolecular ring closures by inclusion of 2-alkenyl, 2-aryl, or 2-oximinyl functionality reacted rather poorly. Profiles of reactant consumption and product formation for these systems were obtained by an in situ NMR monitoring technique. An array of different catalyst forms were tested for efficiency and ease of use. The proposed mechanism, involving hole capture at the TiO2 surface by the carboxylates followed by CO2 loss, was supported by EPR spectroscopic evidence of the intermediates. Deuterium labeling indicated that the titania likely donates protons from surface hydroxyl groups as well as supplying electrons and holes, thus acting as both a catalyst and a reaction partner.

Decatungstate photocatalyzed benzylation of alkenes with alkylaromatics

The direct benzylation of electrophilic al-kenes with alkylbenzenes has been achieved by decatungstate photocatalysis in a high ionic strength medium (5:1 acetonitrile/water mixed solvents, 0.5 M lithium perchlorate). The reaction has been extended to ring-substituted (Cl, F, CN) toluenes and further alkylbenzenes. Intramolecular selectivity (p-cymene, 4-methylanisole) and deuteration effects support the atom transfer character of the process that, however, requires a sufficient stabilization of the intermediate polar exciplex to occur. The reactivity of the deca-tungstate anion is compared with that of aromatic ketones, the benchmark of photochemical hydrogen/ electron transfer processes.

Decatungstate as photoredox catalyst: Benzylation of electron-poor olefins

Excited tetrabutylammonium decatungstate (TBADT), known to activate a variety of compounds via hydrogen atom transfer (HAT), has now been applied as a photoredox catalyst for the effective oxidative cleavage of benzyl silanes and radical benzylation of reducible olefins occurring in isolated yields from poor to excellent.