RuCl(p-cymene)[(R,R)-Ts-DPEN]

• CAS: 192139-92-7
• Catalog Number: ACM192139927
• Category: Main Products
• Molecular Weight: 636.21
• Molecular Formula: C21H21ClN2O2RuS.C10H14
• Synonyms: Chloro{[(1R,2R)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido}(p-cymene)ruthenium(II)
• Appearance: Orange yellow powder
• Application: This catalyst has shown to effect highly enantioselective hydrogenation of functionalized ketones where the substituents are dialkylamino, hydoxy, siloxy, carbonyl, ester, amide or thioester.
• Storage: 2-8°C

Case Study

Recyclable Asymmetric Transfer Hydrogenation in Water Using RuCl(p-cymene)[(R,R)-Ts-DPEN] via Surfactant-Based Delivery

Öztürk, Bengi Özgün, et al. Reaction Chemistry & Engineering 8.2 (2023): 424-431.

This study demonstrated the application of the chiral ruthenium complex RuCl(p-cymene)[(R,R)-Ts-DPEN] in asymmetric transfer hydrogenation (ATH) of ketones under environmentally friendly aqueous conditions. By leveraging non-ionic surfactants for catalyst dissolution and recycling, this approach enabled efficient and reusable enantioselective catalysis on a micellar scale.
The catalytic system was formulated using RuCl(p-cymene)[(R,R)-Ts-DPEN] as the chiral catalyst, non-ionic surfactants Synperonic F108 and Tween 80 to form nanosized micelles (60-90 nm), water as the sole solvent, and a formate donor as the hydrogen source. Reactions were conducted under air without degassing, using microgram quantities of the ruthenium catalyst. The micellar catalyst system was recovered after each cycle via simple phase separation.
Key Results
· The surfactant-encapsulated catalyst exhibited high activity and enantioselectivity in the ATH of acetophenone derivatives.
· The aqueous micellar system allowed efficient recycling of the catalyst for up to 8 consecutive runs without significant loss of enantioselectivity or reactivity.
· The system showed excellent stability under aerobic aqueous conditions, eliminating the need for inert atmosphere handling.

Scalable Kinetic Resolution of Racemic 4-Formyl[2.2]paracyclophane Using RuCl(p-cymene)[(R,R)-Ts-DPEN] via Asymmetric Transfer Hydrogenation

Delcourt, Marie-Léonie, et al. Advanced Synthesis & Catalysis 358.8 (2016): 1213-1218.

RuCl(p-cymene)[(R,R)-Ts-DPEN] can be employed as an efficient catalyst for the kinetic resolution (KR) of racemic 4-formyl[2.2]paracyclophane by means of asymmetric transfer hydrogenation (ATH).
Conditions using standard ATH for the 4-formyl group (HCOOH/Et3N or KOH/i-PrOH, etc.) racemic product or inseparable by-product, leading to a further optimization. Optimized KR-ATH conditions use RuCl(p-cymene)[(R,R)-Ts-DPEN] (2 mol%) as a catalyst, isopropyl alcohol (i-PrOH) as a reducing agent, anhydrous potassium tert-butoxide (t-BuOK, 10 mol%) as a base and an inert atmosphere at -10°C.
Key Results
· Enantioselectivity: The unreacted aldehyde (Rp)-1 could be resolved to >98% ee at 58% conversion. The reduced alcohol (Sp)-2 could be resolved to 62% ee.
· Isolated Yields: Enantiopure (Rp)-1 and (Sp)-2 were obtained in 39% and 41% isolated yield, respectively, both with >99% ee after purification on a gram-scale.
· Scalability: The gram-level reaction demonstrated the scalability of the process for practical applications.
· Side Reactions Mitigated: Anhydrous t-BuOK was employed to minimize the formation of by-products that were prevalent when using weaker bases like KOH.
· Mechanism Insights: The KR-ATH proceeds via selective reduction of one enantiomer of the racemic aldehyde, leveraging the chiral environment provided by RuCl(p-cymene)[(R,R)-Ts-DPEN]. The bulky tert-butoxide base enhances stereocontrol by minimizing non-selective pathways and stabilizing the transition state.

Custom Q&A

What is the PubChem CID for RuCl[(R,R)-Tsdpen](p-cymene)?

The PubChem CID is 46846568.

What is the molecular formula of RuCl[(R,R)-Tsdpen](p-cymene)?

The molecular formula is C31H35ClN2O2RuS.

What is the molecular weight of RuCl[(R,R)-Tsdpen](p-cymene)?

The molecular weight is 636.2 g/mol.

What are the synonyms for RuCl[(R,R)-Tsdpen](p-cymene)?

The synonyms are RuCl[(R,R)-Tsdpen](p-cymene), R0125, A901940, and various other names.

What are the component compounds of RuCl[(R,R)-Tsdpen](p-cymene)?

The component compounds are Ruthenium (CID 23950), p-CYMENE (CID 7463), Hydrochloric Acid (CID 313), and ((1R,2R)-(-)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine) (CID 2734565).

When was RuCl[(R,R)-Tsdpen](p-cymene) created?

It was created on August 23, 2010.

When was RuCl[(R,R)-Tsdpen](p-cymene) last modified?

It was last modified on December 30, 2023.

What is the IUPAC name of RuCl[(R,R)-Tsdpen](p-cymene)?

The IUPAC name is [(1R,2R)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;1-methyl-4-propan-2-ylbenzene;ruthenium(2+);chloride.

What is the InChIKey of RuCl[(R,R)-Tsdpen](p-cymene)?

The InChIKey is AZFNGPAYDKGCRB-AGEKDOICSA-M.

Is RuCl[(R,R)-Tsdpen](p-cymene) the canonical form of the compound?

Yes, RuCl[(R,R)-Tsdpen](p-cymene) is the canonical form of the compound.

What are the synonyms of RuCl[(R,R)-Tsdpen](p-cymene)?

The synonyms are RuCl[(R,R)-Tsdpen](p-cymene), R0125, A901940, ((R,r)-2-amino-1,2-diphenylethyl)[(4-tolyl)sulfonyl]amido](pcymene)ruthenium(II)chloride, and [(R,R)-N-(2-Amino-1,2-diphenylethyl)-p-toluenesulfonamide]chloro(p-cymene)ruthenium(II).

What is the InChI of RuCl[(R,R)-Tsdpen](p-cymene)?

The InChI is InChI=1S/C21H21N2O2S.C10H14.ClH.Ru/c1-16-12-14-19(15-13-16)26(24,25)23-21(18-10-6-3-7-11-18)20(22)17-8-4-2-5-9-17;1-8(2)10-6-4-9(3)5-7-10;;/h2-15,20-21H,22H2,1H3;4-8H,1-3H3;1H;/q-1;;;+2/p-1/t20-,21-;;;/m1.../s1.

What is the canonical SMILES of RuCl[(R,R)-Tsdpen](p-cymene)?

The canonical SMILES is CC1=CC=C(C=C1)C(C)C.CC1=CC=C(C=C1)S(=O)(=O)[N-]C(C2=CC=CC=C2)C(C3=CC=CC=C3)N.[Cl-].[Ru+2].

What is the hydrogen bond donor count of RuCl[(R,R)-Tsdpen](p-cymene)?

The hydrogen bond donor count is 1.

What is the hydrogen bond acceptor count of RuCl[(R,R)-Tsdpen](p-cymene)?

The hydrogen bond acceptor count is 5.

What is the rotatable bond count of RuCl[(R,R)-Tsdpen](p-cymene)?

The rotatable bond count is 7.