7250-12-6

Upstream product

• 107-18-6 allyl alcohol 
• 1711-06-4 3-Methylbenzoyl chloride 
• 106-95-6 allyl bromide 
• 99-04-7 m-Toluic acid 
• 587-03-1 3-methylbenzyl alcohol 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 99-36-5 1-methoxycarbonyl-3-methylbenzene 

Relevant academic research and scientific papers

Enantioselective Three-Component Fluoroalkylarylation of Unactivated Olefins through Nickel-Catalyzed Cross-Electrophile Coupling

A nickel-catalyzed, enantioselective, three-component fluoroalkylarylation of unactivated alkenes with aryl halides and perfluoroalkyl iodides has been described. This cross-electrophile coupling protocol utilizes a chiral nickel/BiOx system as well as a pendant chelating group to facilitate the challenging three-component, asymmetric difunctionalization of unactivated alkenes, providing direct access to valuable chiral β-fluoroalkyl arylalkanes with high efficiency and excellent enantioselectivity. The mild conditions allow for a broad substrate scope as well as good functional group toleration.

Palladium-catalyzed allylic esterification via C-C bond cleavage of a secondary homoallyl alcohol

Palladium-catalyzed allylic esterifications of secondary homoallyl alcohols with acids via sequential retro-allylation and esterification are demonstrated, affording the corresponding allyl ester in up to 99% yield. The electron effect of the substituent of the secondary alcohol was found to be crucial to the selective C-C bond cleavage.

Efficient and simple approaches towards direct oxidative esterification of alcohols

The present article describes novel oxidative protocols for direct esterification of alcohols. The protocols involve successful demonstrations of both "cross" and "self" esterification of a wide variety of alcohols. The cross-esterification proceeds under a simple transition-metal-free condition, containing catalytic amounts of TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy)/TBAB (tetra-n-butylammonium bromide) in combination with oxone (potassium peroxo monosulfate) as the oxidant, whereas the self-esterification is achieved through simple induction of Fe(OAc)2/dipic (dipic=2,6-pyridinedicarboxylic acid) as the active catalyst under an identical oxidizing environment. One-pot oxidative esterification: A wide variety of alcohols undergo transition-metal-free (in the presence of oxone/2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)/tetra-n-butylammonium bromide (TBAB)) selective "cross" esterification in moderate to excellent yields (see Figure). The "self" esterification process has however been achieved in the presence of Fe(OAc)2/2,6-pyridinedicarboxylic acid (dipic) as the active catalytic species under a similar oxidizing environment.

Rhenium-catalyzed allylation of C-H bonds of benzoic and acrylic acids

We have succeeded in the allylation of aromatic and olefinic C-H bonds of benzoic and acrylic acids using a rhenium catalyst, Re2(CO) 10. In this reaction, isomerization of the introduced allyl group to the 1-propenyl group did not occur.

Surfactant-mediated solvent-free dealkylative cleavage of ethers and esters and trans-alkylation under neutral conditions

A simple, surfactant-mediated, one-pot, solvent-free dealkylative cleavage of aryl ethers and esters followed by subsequent optional trans-alkylation under essentially neutral conditions has been developed.