The title compound, C(15)H(15)BrO(2), was synthesized by a Brønsted acid-catalysed domino electrocyclization-halogenation reaction. The five-membered ring is essentially planar (r.m.s. deviation 0.006 Å) and forms a dihedral angle of 72.7 (3)° with the attached phenyl ring. The six-membered heterocycle adopts a half-chair conformation. The crystal packing is stabilized by a C-H⋯O contact.

The CuX (X = I, Br, Cl, CN)-mediated cyclization-halogenation and cyclization-cyanation reactions of beta-hydroxyalkynes and o-alkynylphenol and -aniline derivatives give rise to 3-halo- and 3-cyanofuro[3,2-b]pyrroles, 3-iodo-, 3-bromo-, and 3-cyanobenzofurans, and 3-cyanoindoles, respectively.

Copper-catalyzed ortho-halogenation of C(sp(2))-H bonds directed by a PIP directing group with NXS (X = Cl, Br, I) has been developed. The reaction is scalable and tolerates a broad range of functional groups and heteroarenes, providing an efficient access to halogenated arenes and heteroarenes.

The tetrathiafulvalene-scaffold (TTF) reacts selectively in allylation, acylation, arylation, halogenation, and thiolation reactions via magnesium or zinc derivatives that are obtained by a direct metalation with Mg- and Zn-TMP-bases (TMP = 2,2,6,6-tetramethylpiperidyl). This stepwise functionalization provides access to a range of new mono-, di-, tri-, and tetra-functionalized TTF-derivatives ...

It has been over a half-century since Kornblum demonstrated the conversion of a primary nitroalkane to a carboxylic acid; addition of an amine results in carboxylic acid formation as well. We describe the formation of amides from terminal nitroalkanes in a two-step, one-pot reaction involving tandem halogenation/umpolung amide synthesis (UmAS).

The Cu(I) halide (X = I, Br, Cl) mediated reactions of Cbz-protected cis-2-phenylethenyl-3-hydroxypyrrolidine gave novel 3-halo-2,5-trisubstituted furans in good yields, via a cyclization-halogenation, ring-opening reaction sequence. In contrast, the reactions with CuCN gave mainly the corresponding 3-cyanofuro[3,2-b]pyrrole formed from a cyclization-cyanation reaction.

The intramolecular halogenation of O-methylbenzohydroximoyl halides in the presence of a Ru catalyst and the ligand diphenylacetylene afforded halo substituted aromatic nitriles in a highly regioselective manner. Further, substituted nitriles were converted into substituted tetrazole derivatives in the presence of NaN3 and I2.

A new protocol for the direct two-electron oxidative Umpolung of alkali halide salts is reported. This procedure, relying on the use of a commercially available sulfoxide as the oxidant, allows the electrophilic halogenation of carbonyl compounds as well as halolactonisation reactions to proceed from the corresponding sodium salts, at room temperature and under mild conditions.

Abstract The oxidation resistance of novel γ / ’-strengthened Co-base superalloys is clearly outmatched by their Ni-base counterparts within the high-temperature regime. Therefore, surface modification strategies to foster protective alumina growth seem auspicious. This study elucidates impact fluorination and shot-peening on formation at 900 °C for a quaternary model alloy (Co-Al-W-Ta system) ...