147673-00-5

Upstream product

• 121169-17-3 3-iodo-4-(methoxymethoxy)benzaldehyde 
• 78-80-8 2-methylbut-1-en-3-yne 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 123-08-0 4-hydroxy-benzaldehyde 
• 60032-63-5 4-hydroxy-3-iodo-benzaldehyde 
• 173029-70-4 3-(3-Hydroxy-3-methylbut-3-ynyl)-4-(methoxymethoxy)benzaldehyde 

Downstream Products

• 22944-03-2 Siccayne 
• 121007-19-0 4-hydroxy-3-(3′-methylbut-3′-en-1′-ynyl)-benzoic acid 
• 121007-17-8 4-hydroxy-3-(3-methylbut-3-en-1-yn-1-yl)benzaldehyde 

Relevant academic research and scientific papers

New Synthetic Applications of Water-Soluble Acetate Pd/TPPTS Catalyst Generated in Situ. Evidence for a True Pd(0) Species Intermediate

Studies on the sp-sp intermolecular coupling reactions with the palladium water-soluble catalyst prepared in situ from palladium(II) acetate and sulfonated triphenylphosphine P(C6H4-m-SO3Na)3 (TPPTS) in a homogeneous acetonitrile-water system, without Cu(I) promotor, afford diynes with moderate yields (45-65percent).Under the same conditions, the sp2-sp coupling of 2-iodophenols or 2-iodoanilines and terminal alkynes followed by intramolecular cyclization gives indolic and furanic products in good yields (60-99percent).Under these aqueous conditions, an efficient and short synthesis of eutypine illustrated the synthetic potentiality of the coupling.Furthermore, through a series of kinetic and 31P NMR experiments, we have demonstrated that a mixture of Pd(OAc)2 and TPPTS affords spontaneously a palladium(0) complex, through formation of bivalent complex Pd(OAc)2(TPPTS)2.A detailed mechanism of the reaction has been investigated thoroughly and the pertinent rate constants measured.The resulting palladium(0) complex reacts with phenyl iodide via an oxidative addition.This complex is considerably less reactive than the corresponding complex generated from PPh3, probably due to steric effects.

The Synthesis of Natural Acetylenic Compounds from Eutypa lata (Pers:F.) TUL.

The synthesis of a series of novel acetylenic compounds 1-7, isolated recently from the fungus Eutypa lata, is described.The crucial step is the coupling reaction between protected aryl halogenide and the acetylenic chain as a cuprous acetylide (Scheme I).A more efficient method using bis(triphenylphosphine)palladium dichloride () as catalyst was also carried out with success.