A palladium-catalyzed atom transfer cyclization of unactivated alkyl iodide has been developed. A radical chain mechanism has been proposed for this transformation, which might not involve an alkylpalladium intermediate.

The asymmetric unit of the title compound, C(19)H(19)NP(+)·I(-), contains two tetra-alkyl-phospho-nium cations and two I(-) anions. The P atoms are four-coordinated in distorted tetra-hedral configurations by three phenyl and one methyl C atoms. There are weak intra- and inter-molecular N-H⋯I contacts.

A mechanistic study of arylations of aliphatic alcohols and hydroxide with diaryliodonium salts, to give alkyl aryl ethers and diaryl ethers, has been performed using experimental techniques and DFT calculations. Aryne intermediates have been trapped, and additives to avoid by-product formation originating from arynes have been found. An alcohol oxidation pathway was observed in parallel to ary...

Allenes can be synthesized via the direct SN2' addition of hydride to propargylic alcohols. Previous examples of this approach, however, have involved harsh reaction conditions and have suffered from incomplete transfer of central chirality to axial chirality. Here we show that Cp2Zr(H)Cl can react with the zinc or magnesium alkoxides of propargylic alcohols to generate allenes in good yield an...

A mild method for the regioselective synthesis of propargyl ethers by the coupling of propargyl alcohols with a range of other alcohols is described. The method employs an air- and moisture-tolerant rhenium-oxo complex ((dppm)ReOCl3) as a catalyst for the formation of sp3-carbon-oxygen bonds without the need for prior activation of the propargyl alcohol or deprotonation of the alcohol nucleophi...

We report the regiospecific, rhodium-catalyzed borylation of saturated terminal C-H bonds in molecules with existing functionality. Moderate to good yields were obtained with the organic substrate in excess and as limiting reagent. The borylations of trialkylamines, protected alcohols, protected ketones, and fluoroalkanes occurred regiospecifically at the methyl group that is least sterically h...

Sulfonated hydrothermal carbons show high activity for esterification of palmitic acid with alcohols. However, the catalyst is significantly deactivated upon recovery. Leaching of sulfonated species does not account for this deactivation, which is observed even by pretreatment only with the alcohol under reflux. Solid state NMR shows the presence of chemically bound alkyl groups coming from the...

Homoallenic alcohols are prepared from propargyl vinyl ethers using a trinuclear gold(I)-oxo complex, [(Ph3PAu)3O]BF4, as a catalyst for propargyl Claisen rearrangement at room temperature. The gold(I)-catalyzed reaction is effective for a diverse collection of propargyl vinyl ethers, including substrates containing aryl and alkyl groups at the propargylic position, and hydrogen, aryl, and alky...