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Upstream product

• 614-47-1 1,3-diphenyl-propen-3-one 
• 3592-47-0 Benzaldehyde-d 
• 32461-19-1 (E)-3-deuterio-1,3-diphenyl prop-2-en-1-one 
• 93698-11-4 3-deuterio-1,3-diphenyl-1-propanone 
• 61637-11-4 (2E)-1-phenyl-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 62668-02-4 (E)-1,3-diphenyl-2-propen-1-ol 
• 24547-50-0 β-d₁-chalcone 
• 134-81-6 benzil 
• 21175-64-4 1,1-dideuteriophenylmethanol 
• 42463-63-8 benzyl alcohol-α,α,hydroxy-d3 
• 65-85-0 benzoic acid 
• 94-41-7 benzalacetophenone 

Relevant academic research and scientific papers

Iridium-mediated β-deuteration of enones

Exposure of captodative enone systems to deuterium in the presence of Crabtree's catalyst (1) results in deuteration at the vinylic site β- to the ketone carbonyl, as well as at any accessible ortho-position. β-exchange is also observed during the reducti

Highly selective continuous-flow synthesis of potentially bioactive deuterated chalcone derivatives

The selective synthesis of various dideuterochalcones as potentially bioactive deuterium-labeled products is presented, by means of the highly controlled partial deuteration of antidiabetic chalcone derivatives. The benefits of continuous-flow processing

Palladium-Mediated Tandem Isomerization-Methylenation of Allyl Alcohols: One-Pot Synthesis of 1,5-Diketones

A novel methodology for the synthesis of 1,5-diketones through a one-pot isomerization-methylenation of a variety of allylic alcohols has been established for the first time. This methodology utilizes commercially available palladium acetate and easily accessible BINOL phosphoric acid. Both isomerization of allylic alcohol and oxidation of methanol occurred through a single catalyst. The practical utility of the methodology has been shown by synthesizing substituted pyridines via sequential addition. Mechanistic investigation reveals the isomerization of allylic alcohols to the corresponding ketone, which ultimately undergoes methylenation, leading to 1,5-diketones, having H2 and H2O as the only byproduct.

Potassium Base-Catalyzed Michael Additions of Allylic Alcohols to α,β-Unsaturated Amides: Scope and Mechanistic Insights

We report herein the first KHMDS-catalyzed Michael additions of allylic alcohols to α,β-unsaturated amides through allylic isomerization. The reaction proceeds smoothly in the presence of only 5 mol% of KHMDS to afford a variety of 1,5-ketoamides in high yields. Mechanistic investigations, including experimental and computational studies, reveal that the KHMDS-catalyzed in-situ generation of the enolate from the allylic alcohol through a tunneling-assisted 1,2-hydride shift is the key to the success of this transformation. (Figure presented.).

A Proton-Responsive Pyridyl(benzamide)-Functionalized NHC Ligand on Ir Complex for Alkylation of Ketones and Secondary Alcohols

A Cp*Ir(III) complex (1) of a newly designed ligand L1 featuring a proton-responsive pyridyl(benzamide) appended on N-heterocyclic carbene (NHC) has been synthesized. The molecular structure of 1 reveals a dearomatized form of the ligand. The protonation of 1 with HBF4 in tetrahydrofuran gives the corresponding aromatized complex [Cp*Ir(L1H)Cl]BF4 (2). Both compounds are characterized spectroscopically and by X-ray crystallography. The protonation of 1 with acid is examined by 1H NMR and UV-vis spectra. The proton-responsive character of 1 is exploited for catalyzing α-alkylation of ketones and β-alkylation of secondary alcohols using primary alcohols as alkylating agents through hydrogen-borrowing methodology. Compound 1 is an effective catalyst for these reactions and exhibits a superior activity in comparison to a structurally similar iridium complex [Cp*Ir(L2)Cl]PF6 (3) lacking a proton-responsive pendant amide moiety. The catalytic alkylation is characterized by a wide substrate scope, low catalyst and base loadings, and a short reaction time. The catalytic efficacy of 1 is also demonstrated for the syntheses of quinoline and lactone derivatives via acceptorless dehydrogenation, and selective alkylation of two steroids, pregnenolone and testosterone. Detailed mechanistic investigations and DFT calculations substantiate the role of the proton-responsive ligand in the hydrogen-borrowing process.

New photocatalytic fixed-point deuteration method for carbon-carbon unsaturated bonds

The invention relates to a new photocatalytic fixed-point deuteration method for carbon-carbon unsaturated bonds. The method is characterized in that an olefin or alkyne compound and a deuterium source undergoes a deuteration reaction under the catalysis of a light source and a photocatalyst to obtain a deuterated product, wherein the deuterium source is deuterated water, deuterated alcohol or deuterated acid, and the reaction temperature is between room temperature and 80 DEG C. The fixed-point deuteration reaction of the olefin or alkyne compound is realized under the photocatalysis action of the photocatalyst with environmentally-friendly and cheap deuterated water or a deuteration reagent as a deuterium source to substitute deuterium gas. Compared with traditional deuteration reactions, the method has a higher selectivity, milder reaction conditions and higher economical suitability, and is suitable for large-scale deuterated chemical substance production.

Diels-Alder route to norbornane derived vicinal phosphane/borane frustrated Lewis pairs for the metal-free catalytic hydrogenation of α, β-unsaturated ketones

The [4+2] cycloaddition reaction of the (dimesitylphosphino)cyclopentadienes 5a,b with N-phenylmaleimide gave the norbornene derivative 9. Its reduction with LiAlH4 produced the N-phenylpyrrolidino-annulated system 10. Treatment with Piers' bor

Transition-Metal-Free Highly Chemoselective and Stereoselective Reduction with Se/DMF/H2O System

A novel metal-free reduction system, in which H2Se (or HSe-) produced in situ from Se/DMF/H2O acts as the active reducing species, has been developed. By using water as an inexpensive, safe, and environmentally friendly surrogate as the hydrogen donor, this new reduction system incorporating Se/DMF/H2O displayed high selectivity and good activity in the reduction of α,β-unsaturated ketones and alkynes. Therefore, this reduction system has great potential to be a general and practical reduction methodology in organic transformation.

Transition-Metal-Free Self-Hydrogen-Transferring Allylic Isomerization

Phenanthroline and tert-butoxide have been established as powerful radical initiators in reactions such as the SRN1-type coupling reactions due to the cooperation of large heteroarenes and a special feature of tert-butoxide. The first phenanthroline-tert-butoxide-catalyzed transition-metal-free allylic isomerization is described. The resulting ketones are key intermediates for indenes. The control experiments rule out the base-promoted allylic anion pathway. The radical pathway is supported by experimental evidence that includes kinetic study, kinetic isotope effect, isotope-labeling experiments, trapping experiments, and EPR experiments.

Ruthenium-catalyzed conjugate hydrogenation of ?±,?2-enones by in situ generated dihydrogen from paraformaldehyde and water

Notwithstanding that the highly selective hydrogenation of ?±,?2-enones to allylic alcohols can be realized by using Noyori's Ru bifunctional system, the selective reduction of the C=C bonds in ?±,?2-enones without touching the C=O bonds still lacks a general, simple, and efficient procedure. Ruthenium-catalyzed conjugate hydrogenation of various ?±,?2-enones to saturated ketones with high selectivity was investigated. The most important feature of this procedure was that hydrogen in situ generated from paraformaldehyde (or formalin) and water was employed as the reductant.