A novel amino-thiocarbamate-catalyzed bromolactonization of unsaturated carboxylic acids has been developed. The scope of the reaction is evidenced by 22 examples of γ-lactones with up to 99% yield and 93% ee. The protocol was applied in the enantioselective synthesis of the key intermediates of VLA-4 antagonists.

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Organofluorine compounds have found extensive applications in various areas of science. Consequently, the development of new efficient and selective methods for their synthesis is an important goal in organic chemistry. Here, we present the first Suzuki cross-coupling reaction which utilizes dihalo compounds for the preparation of secondary alkyl fluorides. Namely, an unprecedented use of simple 1-halo-1-fluoroalkanes as electrophiles in C(sp(3))-C(sp(3)) and C(sp(3))-C(sp(2)) cross-couplings allows for the formal site-selective incorporation of F-group in the alkyl chain with no adjacent activating functional groups. Highly effective approach to the electrophilic substrates, 1-halo-1-fluoroalkanes, via iododecarboxylation of the corresponding α-fluorocarboxylic acids is also presented. The conceptually new route to organofluorides was used for the facile preparation of biomedically valuable compounds. In addition, we demonstrated that an asymmetric version of the developed reaction for the stereoconvergent synthesis of chiral secondary alkyl fluorides is feasible.

Porous structure and surface modification have been widely studied in applying metal oxide nanomaterials as Li-ion battery anodes for overcoming problems such as poor conductivity and large volume variation. Here, we demonstrate a direct triple-decomposition process for the in situ synthesis of C/Cu/ZnO porous hybrids. In a typical porous structure, 5-10 nm sized ZnO and Cu nanoparticles aggregate randomly and are modified with carbon layers in thickness of 1 nm. Moreover, the resulted hybrid nanostructures show a high and stable specific capacity of 818 mAh g(-1) at a current rate of 50 mA g(-1) with almost 100% capacity retention for up to 100 cycles when used an anode material for lithium ion batteries. By combination of the structural analyses and electrochemical behaviors, it could be speculated that the porous structure and the modifications of copper nanoparticles and carbon layers are mainly responsible for the dramatically improved electrochemical performance of ZnO anodes.

The incorporation of fluorine atom into a stereogenic center is a highly challenging transformation with current methodologies offering access mainly to chiral α- and β-fluoroalkanes. In this article, the development of a novel general approach to construct β-, γ-, δ-, and ε- fluoroalkanes with good enantioselectivity is described. Different directing groups, such as benzyl, ketone, and sulfonyl, were shown to give good enantioselectivity under Suzuki cross-coupling conditions in the presence of a Ni catalyst and chiral diamine ligand. It includes the first examples of enantioselective synthesis of chiral fluorine-containing centers at as distant as δ or ε positions from the functional groups.