Efficient synthesis of secondary alkyl fluorides via Suzuki cross-coupling reaction of 1-halo-1-fluoroalkanes.

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.

CuO nanoparticles catalyzed C-N, C-O, and C-S cross-coupling reactions: scope and mechanism.

CuO nanoparticles have been studied for C-N, C-O, and C-S bond formations via cross-coupling reactions of nitrogen, oxygen, and sulfur nucleophiles with aryl halides. Amides, amines, imidazoles, phenols, alcohols and thiols undergo reactions with aryl iodides in the presence of a base such as KOH, Cs(2)CO(3), and K(2)CO(3) at moderate temperature. The procedure is simple, general, ligand-free, and efficient to afford the cross-coupled products in high yield.

A novel tandem sequence to pyrrole syntheses by 5-endo-dig cyclization of 1,3-enynes with amines.

The synthesis of pentasubstituted pyrroles has been described using molecular iodine from 1,3-enynes and amines via a sequential tandem aza-Michael addition, iodocyclization, and oxidative aromatization. The protocol is simple and efficient to afford the target products at ambient conditions.

Synthesis, structure, and application of self-assembled copper(II) aqua complex by H-bonding for acceleration of the nitroaldol reaction on water.

Simple addition: Copper(II) aqua complex 1 can be prepared in a one-pot synthesis and is self-assembled by H-bond interactions. Complex 1 is shown to accelerate the nitroaldol reaction on water, which is a heterogeneous process, requiring no additive or base, and 1 can be recycled without loss of activity. Copper(II) aqua complex 1 has been prepared in a one-pot synthesis. The single crystal X-ray analysis showed that the complex is self-assembled through aqua ligands by H-bond interactions and the copper(II) atoms are pentacoordinated with square pyramidal geometry. Complex 1 has been studied for the acceleration of the nitroalodol reaction on water. It is a clean technological process and the catalyst can be recycled without loss of activity.