119784-73-5

Upstream product

• 4392-24-9 Cinnamyl bromide 
• 108-59-8 malonic acid dimethyl ester 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 21040-45-9 Cinnamyl acetate 
• 18424-76-5 dimethyl malonate sodium salt 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 55698-46-9 cinnamyltrimethylammonium iodide 
• 119784-85-9 1-phenyl-5-[[(2E)-3-phenyl-2-propen-1-yl]thio]-1H-tetrazole 

Relevant academic research and scientific papers

Chirality Transfer in Palladium Catalyzed Reactions of Allylammonium Salts

Optically active 1-isobutyl-2(Z)-butenyltrimethylammonium iodide (10) underwent allylation with dimethyl sodiomalonate in the presence of a palladium(0) catalyst.The reaction proceeded predominantly with 1,3 transposition and with inversion of configuration, due probably to a prior isomerization from anti to syn-?-allylpalladium intermediate (1415).The stereochemistry observed in the reaction with phenylzinc chloride was opposite to that with the soft nucleophile.

Integrated electrochemical-chemical oxidation mediated by alkoxysulfonium Ions

Generation of carbocations by the "cation pool" method followed by reaction with dimethyl sulfoxide (DMSO) gave the corresponding alkoxysulfonium ions. Alkoxysulfonium ions could also be generated by in situ DMSO trapping of electrochemically generated carbocations. The resulting alkoxysulfonium ions were transformed into carbonyl compounds by treatment with triethylamine. The present integrated electrochemical-chemical oxidation can be applied to the oxidation of diarylmethanes to diaryl ketones, toluenes to benzaldehydes, and aryl-substituted alkenes to 1,2-diketones. Moreover, the oxidation of unsaturated compounds bearing a nucleophilic group in an appropriate position gives cyclized carbonyl compounds.

N-Heterocyclic carbenes as ligands in palladium-catalyzed Tsuji-Trost allylic substitution

A Pd(0)-catalyzed allylic substitution (i.e., Tsuji-Trost reaction) using N-heterocyclic carbene as a ligand was investigated. It has been proven that an imidazolium salt 2d having bulky aromatic rings attached to the nitrogens in its imidazol-2-ylidene skeleton is suitable as a ligand precursor and that a Pd2dba3-imidazolium salt 2d-Cs2CO3 system is highly efficient for producing a Pd-NHC catalyst in this reaction. Allylic substitution using a Pd-NHC complex differed from that using a Pd-phosphine complex as follows: (1) the reaction using a Pd-NHC complex required elevated temperature (50 °C or reflux in THF), (2) allylic carbonates were inert to a Pd-NHC complex, and (3) nitrogen nucleophiles such as sulfonamide and amine did not react with allylic acetate. It was also found that allylic substitution with a soft nucleophile using a Pd-NHC catalyst proceeds via overall retention of configuration to give the product in a stereospecific manner, the stereochemical reaction course obviously being the same as that of the reaction using a Pd-phosphine complex.

Pd-catalyzed allylic substitution using nucleophilic N-heterocyclic carbene as a ligand

(Matrix presented) A nucleophilic N-heterocyclic carbene has been successfully used in a Pd(0)-catalyzed allylic substitution for the first time. It was found that allylic substitution with a soft nucleophile using a Pd-carbene catalyst proceeds via retention of configuration, the stereochemical reaction pathway being the same as that of the reaction using a Pd-phosphine complex.

SINGLE-STEP PREPARATION OF ALLYLIC SULFIDES HAVING 1-PHENYLTETRAZOLE-5-THIO GROUP FROM ALLYLIC ALCOHOLS USING S,S'-BIS(1-PHENYL-1H-TETRAZOL-5-YL) DITHIOCARBONATE AND REACTIONS INVOLVING THE ALLYLIC SULFIDES

The reaction of allylic alcohols and S,S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate (1) gave allylic sulfides having 1-phenyltetrazole-5-thio group in a single step.Furthermore, these allylic sulfides could be applied to carbon-carbon bond and carbon-sulfur bond formations by using Grignard reagents or carbanions in the presence of catalytic amount of copper(I) bromide or palladium (0), respectively.