58102-69-5

Upstream product

• 54636-56-5 (E)-1-(3-bromoprop-1-en-1-yl)-4-methylbenzene 
• 108-95-2 phenol 
• 624-31-7 4-tolyl iodide 
• 1746-13-0 allyl phenyl ether 
• 106-38-7 para-bromotoluene 
• 122058-30-4 p-methylcinnamyl alcohol 
• 90090-41-8 N-methoxy-4-methylbenzenesulfonamide 

Downstream Products

• 58102-87-7 2-<1-(p-Tolyl)allyl>-phenol 

Relevant academic research and scientific papers

Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide

A novel Pd-catalyzed protocol for the desulfitative Heck-type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtain aryl alkenes. Different substituents on the aromatic ring of N-methoxysulfonamides were also found to be compatible with the reaction conditions. Expectedly, the reaction proceeds through CuCl2-promoted generation of the nitrogen radical and subsequent desulfonylation under thermal conditions to afford the aryl radical for the Pd-catalyzed coupling reaction. N-Methoxysulfonamide was further exploited for the synthesis of symmetrical biaryls in the presence of CuCl2. This journal is

Selective Synthesis of Z-Cinnamyl Ethers and Cinnamyl Alcohols through Visible Light-Promoted Photocatalytic E to Z Isomerization

A photocatalytic E to Z isomerization of alkenes using an iridium photosensitizer under mild reaction conditions is disclosed. This method provides scalable and efficient access to Z-cinnamyl ether and allylic alcohol derivatives in high yields with excellent stereoselectivity. Importantly, this method also provides a powerful strategy for the selective synthesis of Z-magnolol and honokiol derivatives possessing potential biological activity.

An efficient palladium-catalyzed synthesis of cinnamyl ethers from aromatic halides, phenols, and allylic chloride

A one-pot, two-step catalytic protocol for the preparation of cinnamyl ethers from simple and readily available aryl halides, phenols and allyl chloride is reported for the first time. This simple and highly efficient palladium nanoparticles catalytic system shows good regio- and stereoselectivities and affords the desired products in good to high yields (49-85%) from aryl iodides. Furthermore, less reactive aryl bromides can also give the cinnamyl ethers in moderate yields (24-72%).

Catalytic enantioselective aziridoarylation of aryl cinnamyl ethers toward synthesis of trans-3-amino-4-arylchromans

Catalytic enantioselective one-pot aziridoarylation reaction of aryl cinnamyl ethers has been demonstrated in detail. Combination of suitable copper catalyst and chiral bis-oxazoline ligand was found to be very efficient for asymmetric aziridination followed by intramolecular arylation (Friedel-Crafts) reaction to provide a general and direct method for the synthesis of trans-3-amino-4-arylchromans with high regio-, diastereo- (dr > 99:1), and enantioselectivity (up to 95% ee) with moderate yield. trans-3-Amino-4- arylchroman is an advanced intermediate for the synthesis of chromenoisoquinoline compounds such as doxanthrine, a potent and selective full agonist for the dopamine-D1 receptor.

Palladium-catalyzed Mizoroki-Heck reaction of allyl aryl ethers with aryl iodides using phosphine-free hydrazone ligands

Palladium-catalyzed Mizoroki-Heck reaction of allyl aryl ethers with aryl iodides gave aryl cinnamyl ethers using a catalytic amount of Pd(OAc)2 in DMF at 50 °C with phosphine-free hydrazone as a ligand in good yields.