76119-08-9

Upstream product

• 104-54-1 3-Phenylpropenol 
• 870-63-3 prenyl bromide 
• 2327-99-3 1-phenylpropadiene 
• 556-82-1 3-methyl-2-buten-1-ol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 

Downstream Products

• 108970-09-8 (E)-3-Hydroxy-4,4-dimethyl-1-phenyl-1,5-hexadiene 
• 76119-07-8 3-methoxy-4,4-dimethyl-1-phenylhexa-1,5-diene 

Relevant academic research and scientific papers

Pd(O)-PhCOOH catalyzed addition of oxygen pronucleophiles to allenes and internal alkynes

We have developed a catalytic system that enables the addition of alcohols to allenes using a combination of 5 mol% Pd(PPh3)4 and 10 mol% benzoic acid. Likewise, the addition reaction of carboxylic acids to alkynes is described. In all cases the reaction proceeded well, giving the corresponding allylation products in good-to-high yields with high regio- and stereoselectivities.

Radical Borylative Cyclization of 1,6-Dienes: Synthesis of Boron-Substituted Six-Membered Heterocycles and Carbocycles

A radical borylative cyclization reaction of 1,6-dienes was developed to assemble boron-handled six-membered heterocycles and carbocycles. This reaction was initiated by the chemo- and regio-controlled addition of an N-heterocyclic carbene-boryl radical to one of the alkene tethers, followed by an intramolecular 6-exo cyclization to afford a six-membered ring framework. The utility of this method was demonstrated in the synthesis of diverse paroxetine analogues through late-stage derivatization of the boryl functional unit.

Tailoring flavins for visible light photocatalysis: organocatalytic [2+2] cycloadditions mediated by a flavin derivative and visible light

A new application of flavin derivatives in visible light photocatalysis was found. 1-Butyl-7,8-dimethoxy-3-methylalloxazine, when irradiated by visible light, was shown to allow an efficient cyclobutane ring formation via an intramolecular [2+2] cycloaddition of both styrene dienes, considered as electron-rich substrates, and electron-poor bis(arylenones), presumably proceeding via an energy transfer mechanism.

Visible light photocatalysis of [2+2] styrene cycloadditions by energy transfer

Hip to be square: Styrenes participate in [2+2] cycloadditions upon irradiation with visible light in the presence of an iridium(III) polypyridyl complex. In contrast to previous reports of visible light photoredox catalysis, the mechanism of this process involves photosensitization by energy transfer and not electron transfer. Copyright

Base Catalysed Rearrangements involving Ylide Intermediates. Part 4. Sigmatropic Rearrangements of 4-Dimethylaminobutenes and Sigmatropic Rearrangements of 3-Dimethylaminohexa-1,5-dienes

The sighmatropic rearrangement (11) -> (12) of the 9-dimethylamino-9-(1-phenylallyl)fluorene is a stereoselective process (84:16) at 170 deg C.Analogous rearrangements (16) -> (17) of the fluorene derivatives show that the reaction rate is increased by electron donating 9-substituents in the order O- > NMe2 > OMe.Similar substituent effects are observed for the Cope rearrangement (25) -> (26) of hexa-1,5-dienes. 4-Phenyl, 4,4-dimethyl, and 3-dimethylamino substituents are particularly effective in accelerating the rate of the rearrangement (25) -> (26).