Homogeneous Cu/TEMPO catalyst systems (TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) have emerged as some of the most versatile and practical catalysts for aerobic alcohol oxidation. Recently, we disclosed a (bpy)Cu(I)/TEMPO/NMI catalyst system (NMI = N-methylimidazole) that exhibits fast rates and high selectivities, even with unactivated aliphatic alcohols. Here, we present a mechanistic inve...

formation of non bonded organic layer around inorganic particles like iron sulfide and zeolites, was hypothesized as starting point for one of the possible mechanisms of the origin of life on earth. in this study, the general circumstances needed for creation of such organic layer was investigated. an aliphatic hydrocarbon (hexane), an aromatic hydrocarbon (toluene), an alcohol (n-octanol) and ...

Acceptor-less alcohol dehydrogenation reaction allows the co-production of added-value carbonyl compounds and H2 from alcohols. Focusing on supported Ru Cu catalysts, we evaluated support effect 2-octanol 1-octanol identified side products as resulting aldolisation coupling. The most active selective catalysts were then tested aliphatic vicinal-diol octan-1,2-diol highest conversion was reached...

We herein report the Rh(iii)-catalyzed C-H bond activation and addition of benzimidates to aldehydes to afford biologically important phthalides in a single step. The imidate is a novel and unexplored directing group that not only enables C-H bond activation and addition to aldehydes, but also serves to capture the reversibly formed alcohol intermediate. The reaction shows broad scope with a hi...

The utility of the tethered aminohydroxylation (TA) has been demonstrated by synthesis of the complex β-amino acid residue of microsclerodermins A and B. The TA provided a regio- and stereoselective functionalization of a complex homoallylic alcohol. The route includes late-stage introduction of the aliphatic side chain via a cuprate addition and cross metathesis, a tactic designed to render th...

A new aliphatic alcohol, (2R,6R)-oct-7-ene-2,6-diol (1), and seven other known compounds (2-8) were isolated from Acorus gramineus rhizomes. The structure of 1 was elucidated by a combination of extensive spectroscopic analyses, including 2D NMR, HR-MS, and the modified Mosher's method. Compounds 3-8 displayed consistent antiproliferative activities against the cell lines tested with IC50 value...

The chromium-catalyzed enantioselective addition of carbo halides to carbonyl compounds is an important transformation in organic synthesis. However, the corresponding catalytic enantioselective arylation of ketones has not been reported to date. Herein, we report the first Cr-catalyzed enantioselective addition of aryl halides to both arylaliphatic and aliphatic ketones with high enantioselect...

The tert-butoxy derivative is one of the most underused alcohol protecting groups. After having developed an easy and useful protocol for its introduction, we offer here a simple procedure for its removal by treatment with anhydrous CeCl3 and NaI in CH3CN. The procedure led to the successful cleavage of aliphatic and aromatic tert-butyl ethers and was compatible with various other functionaliti...

The secondary kinetic isotope effects for the hydride transfer reactions from aliphatic alcohols to two carbocations (NAD(+) models) in acetonitrile were determined. The results suggest that the hydride transfer takes place by tunneling and that the rehybridizations of both donor and acceptor carbons lag behind the H-tunneling. This is quite contrary to the observations in alcohol dehydrogenase...

The title compound, C(5)H(13)NO, is an aliphatic amino-alcohol with both functional groups residing on terminal C atoms. Apart from the hy-droxy group, all non-H atoms are nearly co-planar, the maximum deviation of an atom taking part in the least-squares plane defined by the mentioned non-H atoms being 0.029 (1) Å. In the crystal, O-H⋯N and N-H⋯O hydrogen bonds connect the mol-ecules, forming ...