33716-94-8

Upstream product

• 768-03-6 Phenyl vinyl ketone 
• 936-59-4 3-chloropropiophenone 
• 100-52-7 benzaldehyde 
• 3592-47-0 Benzaldehyde-d 
• 1826-67-1 vinyl magnesium bromide 
• 4393-06-0 1-Phenyl-2-propen-1-ol 

Downstream Products

• 43006-74-2 3-deuterio-1-phenylpropan-1-one 
• 76973-09-6 propiophenone-α-d₁ 
• 894805-59-5 C₁₆H₁₅⁽²⁾HO₂ 
• 894805-61-9 C₁₆H₁₄⁽²⁾H₂O₂ 
• 71908-02-6 (2SR,3RS)-3-hydroxy-2-methyl-1,3-diphenylpropan-1-one 
• 71908-03-7 (2SR,3RS)-2-methyl-1,3-diphenyl-3-hydroxypropan-1-one 
• 93-55-0 1-phenyl-propan-1-one 
• 1431732-16-9 C₁₇H₁₇⁽²⁾HO₃ 

Relevant academic research and scientific papers

Rhodium(iii)-catalyzed C-H allylation of indoles with allyl alcohols: Via β-hydroxide elimination

An efficient Rh(iii)-catalyzed dehydrative C-H allylation of indoles with allyl alcohols via β-hydroxide elimination under oxidant-free conditions has been developed. This method features very mild reaction conditions, excellent regioselectivity and stere

Asymmetric Synthesis of γ-Secondary Amino Alcohols via a Borrowing-Hydrogen Cascade

The borrowing-hydrogen (or hydrogen autotransfer) process, where the catalyst dehydrogenates a substrate and formally transfers the H atom to an unsaturated intermediate, is an atom-efficient and environmentally benign transformation. Described here is an example of an asymmetric borrowing-hydrogen cascade for the formal anti-Markovnikov hydroamination of allyl alcohols to synthesize optically enriched γ-secondary amino alcohols. By exploiting the Ru-(S)-iPrPyme catalyst with minimal stereogenicity, a cascade process including dehydrogenation, conjugate addition, and asymmetric reduction was developed. The mild conditions, functional group tolerance, and broad substrate scope (54 examples) demonstrate the synthetic practicality of the catalytic system.

Ruthenium-Catalyzed Redox Isomerizations inside Living Cells

Tailored ruthenium(IV) complexes can catalyze the isomerization of allylic alcohols into saturated carbonyl derivatives under physiologically relevant conditions, and even inside living mammalian cells. The reaction, which involves ruthenium-hydride intermediates, is bioorthogonal and biocompatible, and can be used for the "in cellulo" generation of fluorescent and bioactive probes. Overall, our research reveals a novel metal-based tool for cellular intervention, and comes to further demonstrate the compatibility of organometallic mechanisms with the complex environment of cells.

Building molecular complexity via tandem ru-catalyzed isomerization/C-H activation

A tandem isomerization/C-H activation of a My lie alcohols was performed using a catalytic amount of RuCI2(PPh3)3. A variety of ortho alkylated ketones have been obtained in excellent yields. This tandem process relies on an in situ generation of a carbonyl functional group that directs the ortho C-H bond activation.

Efficient synthesis of β-hydroxy ketones from allylic alcohols by catalytic formation of ruthenium enolates

A study was conducted to demonstrate the synthesis of β-hydroxy ketones from allylic alcohols by catalytic formation of ruthenium enolates. KOtBu was added to a mixture of complex Ru, containing a cyclopentadienyl ligand bearing five phenyl groups. It was demonstrated that ruthenium chloride reacts with KOtBu, forming a ruthenium tert-butoxide complex. It was also demonstrated that the reaction of the tert-butoxide complex with allylic alcohol produced a new alkoxide, as detected by H NMR spectroscopy.

Pentamethylcyclopentadienyl ruthenium: an efficient catalyst for the redox isomerization of functionalized allylic alcohols into carbonyl compounds

The catalytic activity of the ruthenium(II) complex [RuCp*(CH3CN)3][PF6] 1 in the transposition of allylic alcohols into carbonyl compounds, in acetonitrile, is reported. This catalyst has proven to be able to catalyze the transformation of poorly reactive and/or functionalized substrates under smooth conditions.

From allylic alcohols to aldols through a new nickel-mediated tandem reaction: Synthetic and mechanistic studies

Nickel hydride type complexes have been successfully developed as catalysts for the tandem isomerization-aldolization reaction of allylic alcohols with aldehydes. Optimization of the reaction conditions has shown that a cocatalyst, such as MgBr2, has a very positive effect on the kinetics of the reaction and in the yields of aldols. Under such optimized conditions {[NiHCl(dppe)] + MgBr2 at 3-5 mol %)}, this reaction affords the aldols in good to excellent yields. It is a full-atom-economy-type reaction that occurs under mild conditions. Furthermore, it has a broad scope for the allylic alcohols and it is compatible with a wide range of aldehydes, including very bulky derivatives. The reaction is completely regioselective, but it exhibits a low stereoselectivity, except for allylic alcohols with a bulky substituent at the carbinol center. The use of chiral non-racemic catalysts was not successful, affording only racemic compounds. However, it was possible to use asymmetric synthesis for the preparation of optically active aldols. Various mechanistic studies have been performed using, for instance, a deuterated alcohol or a deuterated catalyst. They gave strong support to a mechanism involving first a transition-metal-mediated isomerization of the allylic alcohol into the free enol, followed by the addition of the latter intermediate onto the aldehyde in an "hydroxyl-carbonyl-ene" type reaction. These results confirm that allylic alcohols can be considered as new and useful partners in the development of the aldol reaction.

Rhodium promoted isomerisation of allylic alkoxides: A new method for enolate anion formation

Transition metal mediated isomerisation of allylic alkoxides is presented as a new method for enolate anion generation. The scope and limitations of enolate formation with the catalysts [Rh(dppe)(THF)2]+ClO4- and (Ph3P)3RhCl are explored and the synthetic potential of the methodology demonstrated in the stereoselective formation and reactions of certain ketone and aldehyde enolates.