33651-05-7

Upstream product

• 1074-12-0 phenylglyoxal hydrate 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 2235-83-8 5-phenyl-2-pentanone 
• 1009-14-9 phenyl butyl ketone 
• 536-74-3 phenylacetylene 
• 68091-91-8 (Z)-(1-bromopenta-1,4-dienyl)benzene 
• 52917-14-3 (Z)-1-Chlor-1-phenyl-1,4-pentadien 
• 142896-16-0 (E)-1-Phenyl-3-(tri-n-butylstannyl)-2-propen-1-one 
• 75-36-5 acetyl chloride 
• 61752-66-7 (E)-1-phenyl-2-penten-1-one 

Relevant academic research and scientific papers

Aerobic Oxidative Dehydrogenation of Ketones to 1,4-Enediones

An efficient and unprecedented strategy for the synthesis of 1,4-enediones from saturated ketones has been developed via palladium-catalyzed oxidative dehydrogenation. The protocol employs molecular oxygen as the sole oxidant and represents an atom- and step-economic process. The approach showed broad substrate scope, good functional group tolerance, and complete E-stereoselectivity. The reaction mechanism has been investigated through deuterium-labeling experiments and intermediate experiments.

Catalyst-Controlled, Enantioselective, and Diastereodivergent Conjugate Addition of Aldehydes to Electron-Deficient Olefins

A chiral-amine-catalyzed enantioselective and diastereodivergent method for aldehyde addition to electron-deficient olefins is presented. Hydrogen bonding was used as a control element to achieve unusual anti selectivity, which was further elucidated through mechanistic and computational studies.

A mild, catalytic, and highly selective method for the oxidation of α,β-enones to 1,4-enediones

A new and simple method is described for the one-step oxidation of α,β-enones to 1,4-enediones in good yields (generally 80-90%) using t-butylhydroperoxide as stoichiometric oxidant and 20% Pd(OH)2 on carbon (5 mol %) as catalyst in CH2Cl2 solution. The same reagents have been used to convert ethylene ketals of α,β-enones to the corresponding monoethylene ketals of 1,4-enediones. Seven representative examples are presented in Table 1. All of the available evidence on these oxidations points to a radical-chain mechanism initiated by the tert-butylperoxy radical (see Scheme 1). γ-tert-Butylperoxy ethers are formed as major products in the oxidation of α,β-enones possessing only a single γ-hydrogen. Copyright

Multifunctional palladium catalysis. 2. Tandem haloallylation followed by Wacker-Tsuji oxidation or Sonogashira cross-coupling

(equationpresented) Multifunctional palladium catalysis is utilized in the one-pot stereocontrolled synthesis of tetrasubstituted methyl ketones and enynes. The homogeneous palladium dihalide catalyst utilized for the bromo-/chloroallylation of alkynes is

Lithiated 3-Tosylpropanal and 4-Tosyl-2-butanone Dimethyl Acetals as β-Acylvinyl Anion Equivalents for the Synthesis of Unsaturated 1,4-Dicarbonyl Compound and α,β-Butenolides

The lithiation of 1,1-dimethoxy-3-tosyllpropane (7a) and 2,2-dimethoxy-4-tosylbutane (7b) followed by reaction with acyl chlorides affords, after p-toluenesulfinic acid elimination, ene-1,4-dicarbonyl compounds in a stereoselective manner.In the case of compound 7a, derived from acrolein, sequential monolithiation and reaction with carbonyl compounds give cyclic acetals, which after oxidation and elimination of p-toluenesulfinic acid are transformed into α,β-butenolides.

Palladium-Catalyzed Reductive Coupling of Acid Chlorides with β-Stannyl Enones: Synthesis of 1,4-Diketones and Mechanistic Aspects

The palladium-catalyzed coupling of acid chlorides with (E)-1,2-bis(tri-n-butylstannyl)ethene or β-stannyl enones gives butane-1,4-diones directly by reduction of the intermediate enedicarbonyl intermediate.The double bond conjugated with a single carbonyl group was not significantly reduced.The generality of the method is illustrated by two syntheses of the 1,4-diketone ipomeanine.By performing the reaction at lower temperatures, α,β-unsaturated 1,4-diketones can also be prepared.The reduction of the intermediate α,β-unsaturated 1,4-diketones probably proceeds by insertion of a palladium hydride, formed in situ by reaction of a Pd(II) complex with Bu3SnCl, followed by hydrolysis of the intermediate palladium enolate.

Synthesis of 1,4-Diketones by Palladium-Catalyzed Reductive Coupling of Acid Chlorides with (E)-1,2-Bis(tri-n-butylstannyl)ethene or β-Stannyl Enones

The palladium-catalyzed coupling of acid chlorides with (E)-1,2-bis(tri-n-butylstannyl)ethene or β-stannyl enones gives butane-1,4-diones directly by reduction of the intermediate enedicarbonyl derivative by a palladium hydride derived from n-Bu3SnCl.

Stereospecific Epoxidation of cis-2-Butene-1,4-diones to cis-2,3-Epoxybutane-1,4-diones with Oxodiperoxomolybdenum (VI), MoO5*H2O*HMPA

The epoxidation of cis-2-butene-1,4-diones 4 with (aqua)(hexamethylphosphoramide)oxodiperoxomolybdenum (VI), MoO5*H2O*HMPA, occured stereospecifically to give the cis-epoxides 5, whose stereochemistry was assigned on the basis of chemical evidence and a comparision of their spectral data with those of the corresponding trans-epoxides 6, which were prepared by the epoxidation of the trans-olefins 3 with alkaline hydrogen peroxide.