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...

A set of reaction conditions has been established to facilitate the non-precious copper-catalyzed enantioselective hydrosilylation of a number of structurally diverse β-, γ- or ε-halo-substituted alkyl aryl ketones and α-, β- or γ-halo-substituted alkyl heteroaryl ketones under air to afford a broad spectrum of halo alcohols in high yields and good to excellent enantioselectivities (up to 99% e...

ABSTRACT Ru-catalyzed synthesis of mixed alkyl-alkyl acetals via addition of primary alcohols to allyl ethers has been extended to include long-chain and/or functionalized substrates. The catalytic systems for these reactions were generated from RuCl2(PPh3)3 and [RuCl2(1,5-COD)]x and phosphines [PPh3 or P(p-chlorophenyl)3] or SbPh3. Of particular importance is the almost quantitative eliminatio...

The anti-mycobacterial activities of nine series of dicarboxyl and tricarboxyl dendritic amphiphiles with one alkyl, two alkyl, and cholestanyl tails against Mycobacterium abscessus, Mycobacterium avium, Mycobacterium chelonae, Mycobacterium marinum and Mycobacterium smegmatis have been measured. The dendritic amphiphiles overcame the limited aqueous solubility of natural long-chain fatty acids...

It was observed that a PhSiH2I-mediated protocol using PhSiH3 and cat. I2 caused the deiodination of 2-(iodomethyl)-2-phenyltetrahydrofuran. Stemming from the investigation of the mechanism, we found that the PhSiH3-I2 system selectively promotes diverse cascade transformations from cyclic ethers to acyclic alkyl iodides, and the PhSiH3-N-iodosuccinimide (NIS) system also promotes cascade trans...

The synthesis of chiral tetrahydrofurans and pyrrolidines starting from 1,2-diols or β-amino alcohols, respectively, by visible-light-mediated deoxygenation is described. Easily accessible monoallylated/propargylated substrates were activated either as inexpensive ethyl oxalates or as recyclable 3,5-bis(trifluoromethyl)benzoates to generate alkyl radicals suitable for 5-exo-trig/5-exo-dig cycli...

Iridium-catalyzed selective α-dimethylation and α-methylation of ketones or phenylacetonitriles, using methanol as the methylating agent, were achieved. In addition, three-component cross α-methyl-alkylation was successfully performed using methyl ketones with methanol and primary alcohols with long-chain alkyl groups. This method provides a very convenient direct route to α-methylated ketones,...

A series of Ru(II) (η(6)-arene) complexes with 1,2,3-triazolylidene ligands comprising different aryl and alkyl wingtip groups have been prepared and characterized by NMR spectroscopy, microanalysis, and in one case by X-ray diffraction. All complexes are active catalyst precursors for the oxidation of alcohols to the corresponding aldehydes/ketones without the need of an oxidant or base as add...