150357-72-5

Upstream product

• 120-57-0 piperonal 
• 39598-55-5 (bromomethylene)triphenylphosphorane 
• 2373-80-0 3,4-(methylenedioxy)cinnamic acid 

Downstream Products

• 57134-53-9 3,4-methylenedioxyphenylethyne 
• 1381775-67-2 2-((E)-2-(benzo[d][1,3]dioxol-5-yl)vinylthio)-5-(trifluoromethyl)phenol 
• 1381775-66-1 2-((E)-2-(benzo[d][1,3]dioxol-5-yl)vinylthio)-5-fluorophenol 
• 1381775-71-8 2-((E)-2-(benzo[d][1,3]dioxol-5-yl)vinylthio)-4,5-dichlorophenol 
• 1621107-18-3 ethyl 2-((1R,2S,3R)-3-(benzo[d][1,3]dioxol-5-yl)-2-nitro-5-oxocyclohexyl)acetate 
• 868559-02-8 2-iodo-1-[3,4-methylenedioxyphenyl]ethylene 
• 26356-44-5 5-((9H-fluoren-9-ylidene)methyl)benzo[d][1,3]dioxole 
• 74809-47-5 (Z)-2-(4,5-methylenedioxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethene 
• 74809-46-4 (E)-5-(3,4,5-trimethoxystyryl)benzo[d][1,3]dioxole 
• 135283-62-4 (+/-)-(3R*,3aS*,7aS*)-N-Benzyl-3-(1,3-benzodioxol-5-yl)-4-oxooctahydroindole 
• 135191-29-6 (+/-)-cis-2-N-Benzyl-6a<(E)-2-(1,3-benzodioxol-5-yl)ethenyl>-1-oxa-3-azabicyclo<3.3.0>octane 

Relevant academic research and scientific papers

Gold- or Silver-Catalyzed Syntheses of Pyrones and Pyridine Derivatives: Mechanistic and Synthetic Aspects

3-Oxo-5-alkynoic acid esters, on treatment with a carbophilic catalyst, undergo 6-endo-dig cyclization reactions to furnish either 2-pyrones or 4-pyrones in high yields. The regiochemical course can be dialed in by the proper choice of the alcohol part of the ester and the π-acid. This transformation is compatible with a variety of acid-sensitive groups as witnessed by a number of exigent applications to the total synthesis of natural products, including pseudopyronine A, hispidine, phellinin A, the radininol family, neurymenolide, violapyrone, wailupemycin and an unnamed brominated 4-pyrone of marine origin. Although the reaction proceeds well in neutral medium, the rate is largely increased when HOAc is used as solvent or co-solvent, which is thought to favor the protodeauration of the reactive alkenyl-gold intermediates as the likely rate-determining step of the catalytic cycle. Such intermediates are prone to undergo diauration as an off-cycle event that sequesters the catalyst; this notion is consistent with literature data and supported by the isolation of the gem-diaurated complexes 12 and 15. Furthermore, silver catalysis allowed access to be gained to 2-alkoxypyridine and 2-alkoxyisoquinoline derivatives starting from readily available imidate precursors.

Palladium(0)-catalyzed cross-coupling of 1,1-diboronates with vinyl bromides and 1,1-dibromoalkenes

Palladium-catalyzed cross-coupling reactions of 1,1-diboronates with vinyl bromides and dibromoalkenes were found to afford 1,4-dienes and allenes, respectively. These reactions utilize the high reactivities of both 1,1-diboronates and allylboron intermediates generated in the initial coupling.

Regioselective copper(I)-catalyzed C-H hydroxylation/C-S coupling: Expedient construction of 2-(styrylthio)phenols

Regioselective copper(I)-catalyzed C-H hydroxylation/C-S coupling of aryl thiols with vinyl halides was developed. Starting from substituted aryl thiols and vinyl halides, various 2-(styrylthio)phenol derivatives were efficiently prepared. The application of the synthetic methodology to generate the bioactive organic intermediate was also exemplified.

A convenient synthesis of 1-bromoolefins and acetylenes by a chain extension of aldehydes

Aldehydes are easily converted to 1-bromoolefins or terminal acetylenes by the use of Wittig reaction of bromomethylenetriphenylphosphorane which is prepared from bromomethyltriphenylphosphonium bromide with potassium tert-butoxide.