Functionalized-arene ruthenium half-sandwich compounds as enantioselective hydrogen transfer catalysts. Crystal structures of [RuCl{TsNCH(R)CH(R)NH2}(η6-C6H5OCH2CH2OH)] (R=H or Ph)

A Convenient One-Pot Synthesis of a Functionalized-Arene Ruthenium Half-Sandwich Compound [RuCl2(η6-C6H5OCH2CH2OH)]2

Development of chiral ligands is the most fundamental task in metal-catalyzed asymmetric synthesis. In the last 60 years, various kinds of ligands have been sophisticatedly developed. However, it remains a long-standing challenge to develop practically useful chiral η6-arene ligands, thereby seriously hampered the asymmetric synthesis promoted by arene-metal catalysts. Herein, we report the design and synthesis of a class of readily tunable, C2 symmetric chiral arene ligands derived from [2.2]paracyclophane. Its ruthenium(II) complexes have been prepared and successfully applied in the enantioselective C-H activation to afford a series of axially chiral isoquinolones (up to 99% yield and 96% ee). This study not only lays chemists' longstanding doubts about whether it is possible to use chiral arene ligand to stereocontrol ruthenium(II)-catalyzed asymmetric C-H activation, but also opens up a new avenue to achieve asymmetric C-H activation.

/pdf/chiral-arene-ligand-as-stereocontroller-for-asymmetric-c-h-18ra159u.pdf

Chiral Arene Ligand as Stereocontroller for Asymmetric C-H Activation.

p-Cymene ruthenium(II) complex is one of the most widely used catalysts in C-H activation. However, enantioselective C-H activation promoted by arene ruthenium(II) complexes has not been realized until recently. The revealed strategies include use of intramolecular nitrene C-H insertion, chiral transient directing group, chiral carboxylic acid, relay catalysis, and chiral arene ligands. In this minireview, these advances are summarized and discussed in hope of spurring further developments.

Enantioselective C-H bond Functionalizations Involving Arene Ruthenium(II)-Catalysis.

Dangling or tethering the side chain: (η6-(R)-3-phenylbutanol)Ru(II) complexes: Chiral arene ruthenium complexes: Part 5.

Chiral or achiral (arene)(COD)Ru complexes can be made by replacing the η6-ligands of (η4-1,5-COD)(η6-1,3,5-cyclooctatriene)Ru (1) or (η4-1,5-COD)(η6-naphthalene)Ru (2) by a suitable arene. This well known reaction has been extended to mono- and dibromoarenes and we report a novel route to substituted (arene)(COD)Ru species, utilizing (bromoarene)-(COD)Ru as starting materials. These facilitate a rapid bromine-lithium exchange reaction with nBuLi at low temperatures and the lithiated species react readily with alkyl chloroformates as electrophiles. By using chiral electrophiles [alkyl = (-)-menthyl] enantiomerically pure or diastereomeric complexes containing CO2R* groups are formed, depending on the symmetry of the original complex. A diastereomeric 1:1 mixture was separated by recrystallization. All (arene)-(COD)Ru complexes tested so far are useful as catalysts for the hydrogenation of simple alkenes at room temperature.

A Specific Route to Enantiomerically Pure Asymmetric (η6-Arene)(η4-1,5-cyclooctadiene)Ru(0) Complexes

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A Specific Route to Enantiomerically Pure Asymmetric (η6-Arene)(η4-1,5-cyclooctadiene)Ru(0) Complexes