Ruthenium(II) Complexes of Monodonor Ligands:  Efficient Reagents for Asymmetric Ketone Hydrogenation

Abstract

[Chemical reaction: See text] A series of BINOL-derived ligands have been prepared and incorporated into ruthenium(II) complexes containing a diamine ligand. The complexes have proven to be excellent catalysts for the asymmetric hydrogenation of ketones, giving reduction products with enantiomeric excesses of up to 99%.

A Fluorescent Chemosensor for Transition‐Metal Ions Based on Optically Active Polybinaphthyl and 2,2′‐Bipyridine

“…R-M-2 was synthesized from (R)-BINOL by a six-step reaction (Scheme 2). [48][49][50][51][52][53][54][55][56] R-3 was synthesized by the same procedure as R-M-2. (R)-6,6 0 -dibromo-2,2 0 -binaphthol and (R)-6,6 0 -dibromo-2,2 0 -bis(methoxymethoxy)-1,1 0 -binaphthyl were prepared and purified according to the literature.…”

“…(R)-6,6 0 -dibromo-2,2 0 -binaphthol and (R)-6,6 0 -dibromo-2,2 0 -bis(methoxymethoxy)-1,1 0 -binaphthyl were prepared and purified according to the literature. [48][49][50][51][52] Optically-active BINOL has often been used as the starting material for the preparation of conjugated polymers that have a main-chain chiral configuration. The skeletal structure of BINOL can be selectively halogenated at the 3,3 0 -or 6,6 0 -positions of 1,1 0 -binaphthyl.…”

“…[57][58][59] Previously, it was found that BINOL could be specifically brominated at the 6,6 0 -positions to give the corresponding chiral product 6,6 0 -dibromo-2,2 0 -binaphthol with 2.0 equiv of bromine. [48][49][50][51][52] According to reports by Li and Pu, [48,60,61] 4,4 0 ,6,6 0 -tetrabromo-2,2 0 -binaphthol could be directly synthesized with an excess amount of bromine. The bromination substitution, however, could take place at the 4,4 0 -positions while the 6,6 0 -positions of BINOL were occupied by chlorine atoms and the BINOL's hydroxyl groups were etherized by ethyl groups.…”

Tunable properties based on regioselectivity of 1,2,3-triazole units in axially chiral 2,2′-linked 1,1′-binaphthyl-based copolymers for ions and acid responsiveness

“…[16,17] Due to the challenging functionalization of the BINap units, [18] most of the previous reports were focused on their incorporation through positions 3 and 3´ or 6 and 6´. [19][20][21][22] Optically active conjugated polymers with a BINap unit in the polymeric backbone linked through the 2 and 2´ positions are rare, [23] however, chiroptical signal is expected to be more sensitive for changes after interaction with externally stimulus because of proximity of dihedral axis of the binaphthyl units.…”

The Use of Copper and Vanadium Mineral Ores in Catalyzed Mechanochemical Carbon–Carbon Bond Formations

“…Practical hurdles such as the scarce solubility of minerals in commonly used reaction media may be responsible for the slow adoption of mineral-catalyzed organic transformations. Seeing the potential and the opportunities of recently implemented mechanochemical techniques to synthesize minerals [6][7][8][9] and to facilitate the development of a myriad of reactions in organic chemistry, [10][11][12][13][14][15] we started wondering about developing mechanochemical mineral-catalyzed transformations.…”