82895-37-2

Upstream product

• 2637-34-5 2-Sulfanylpyridine 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 13327-62-3 2-mercaptopyridine sodium salt 
• 2637-34-5 pyridine-2-thione 
• 106625-69-8 ethyl (E)-3-phenyl-2-propenyl carbonate 
• 87802-71-9 (E)-methyl cinnamyl carbonate 

Downstream Products

• 97522-62-8 C₁₅H₁₁NOS 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 

Relevant academic research and scientific papers

Palladium(0)-catalyzed alkylation of thiols

Palladium(0)-catalyzed alkylation of various allylic carbonates by aromatic thiols allowed the easy preparation of various allylic aryl sulphides in quite good yields. The reaction was regioselective with substitution at the less hindered side of the π-allyl system whatever the temperature of the reaction, and was diastereoselective with net retention of configuration.

Palladium-catalyzed allylation of pyrimidine-2,4-diones (uracils) and of 6-membered heterocyclic ambident sulfur nucleophiles

Pd(O)-Catalyzed allylation of six-membered ambident heterocycles bearing NH-CO, NH-CS and CH2-CO moieties obey the regioselectivity rules: C>O; N>O; S>N; NH-CO>NH-CS. Uracil and 5-methyluracil (thymine) do not show regioselectivity (N-1 = N-3) whereas 6-methyluracil is regioselectively allylated at N-3 (N-3>N-1).

Stereochemistry of direct olefin formation from carbonyl compounds and lithiated heterocyclic sulfones

The conditions for the title reaction were studied for the 2-benzothiazole and 2-pyridine series and for some examples in the 2-pyrimidine series.The olefin preparations were generally observed to be more efficient for 2-BT-sulfone systems.From the data of the hundred cases studied, it can be concluded that (E)-olefins are obtained: (i) from saturated BT-sulfones and aromatic aldehydes; and (ii) from benzylic BT-sulfones and branched saturated aldehydes (isobutyraldehyde, pivalaldehyde) or α,β-ethylenic or aromatic aldehydes. (Z)-olefins arise: (i) fom propargylic BT-sulfones and saturated or aromatic aldehydes; and (ii) from allylic or benzylic Pyr-sulfones and saturated aldehydes.Possible mechanisms for this new olefination procedure were examined. - heteroaromatic sulfones, organolithium derivatives, intramolecular ipso reactions, stereochemistry, elimination, olefination.

Synthesis of allyl aryl sulphides by palladium(0)-mediated alkylation of thiols

Various allylic aryl sulphides are readily prepared in high yields by the palladium(0)-catalyzed S-alkylation of allylic carbonates by various aromatic thiols.

A NEW SYNTHESIS OF 1,3-DIENES FROM ALLYL SULFIDES AND ALLYL SULFONES USING TRI-n-BUTYLSTANNYLMETHYL IODIDE

Allyl 2-pyridyl sulfide 6 or allyl phenyl sulfone 7 on treatment with n-butyllithium in tetrahydrofuran followed by tri-n-butylstannylmethyl iodide (4) afforded directly the 1,3-diene 8 in good yield.