A copper-catalysed direct radical alkenylation of various benzyl bromides and α-carbonyl alkyl bromides has been developed. Compared with the recent radical alkenylations which mostly focused on secondary or tertiary alkyl halides, this transformation shows good reactivity to primary alkyl halides and tertiary, secondary alkyl halides were also tolerated. The key initiation step of this transfo...

An efficient synthesis of 2H-thiopyran derivatives via three-component reaction of alkyl propiolate, benzoyl isothiocyanate or its derivatives and alkyl bromides in the presence of triphenylphosphine in water at 80o C without using any catalyst in water is described. The method offers several advantages including high yields of products and an easy work-up procedure.

The first method for achieving alkyl–alkyl Suzuki reactions of unactivated secondary alkyl chlorides has been developed. Carbon–carbon bond formation occurs under mild conditions (at room temperature) with the aid of commercially available catalyst components. This method has proved to be versatile: without modification, it can be applied to Suzuki reactions of secondary and primary alkyl bromi...

Cross-linking of the reverse micelles (RMs) of a triallylammonium surfactant afforded organic nanoparticles with introverted cationic groups. The cross-linked reverse micelles catalyzed size-selective biphasic reaction between sodium azide and alkyl bromides. Size selectivity of up to 9:1 was obtained for alkyl bromides with similar structures. The selectivity was influenced strongly by the siz...

Two series of long chain imidazolium- and pyridinium-based ionic liquids containing an ester functional group in the alkyl side chain, 3-methyl-1-alkyloxycarbonylmethylimidazolium bromides (C(n)EMeImBr) and 1-alkyloxycarbonylmethylpyridinium bromides (C(n)EPyrBr), were synthesized and their thermal stability, aggregation behavior in aqueous medium, and antimicrobial activity investigated. The i...

Hydrocarbons are still the most important precursors of functionalized organic molecules, which has stirred interest in the discovery of new C-H bond functionalization methods. We describe herein a new step-economical approach that enables C-C bonds to be constructed at the terminal position of linear alkanes. First, we show that secondary alkyl bromides can undergo in situ conversion into alky...

Preassociation of the substrate close to photoredox catalyst increases its efficiency, shown using pillarene-bound phenothiazines in reduction alkyl bromides.

A convenient one-pot approach to alkylcyanobiaryls is described. The method is based on biaryl cross-coupling between the sodium salt of the terephthalonitrile dianion and a neutral aromatic nitrile in liquid ammonia, and successive alkylation of the long-lived anionic intermediate with alkyl bromides. The reaction is compatible with benzonitriles that contain methyl, methoxy and phenyl groups,...

A simple protocol for iron-catalyzed cross-coupling of nonactivated secondary alkyl bromides and iodides with alkynyl Grignard reagents at room temperature has been developed. A wide range of secondary alkyl halides and terminal alkynes are tolerated to afford the substituted alkynes in good yields. A slight modification of the reaction protocol also allows for cross-coupling with a variety of ...

Hypervalent alkylsilicates represent new and readily accessible precursors for the generation of alkyl radicals under photoredox conditions. Alkyl radicals generated from such silicates serve as effective hydrogen atom abstractors from thiols, furnishing thiyl radicals. The reactive sulfur species generated in this manner can be funneled into a nickel-mediated cross-coupling cycle employing aro...