30765-84-5

Upstream product

• 68-34-8 phenyl toluenesulfonamide 
• 106-95-6 allyl bromide 
• 4165-79-1 1,1-diphenyl-3-buten-1-ol 
• 62-53-3 aniline 
• 98-59-9 p-toluenesulfonyl chloride 
• 101283-69-6 4-methyl-N-phenyl-N-(prop-2-yn-1-yl)benzenesulfonamide 
• 589-09-3 N-allyl-N-phenylamine 
• 107-05-1 3-chloroprop-1-ene 

Downstream Products

• 87929-23-5 2-Chloromethyl-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]thiazine 
• 37877-46-6 N-propyl-toluene-4-sulfonanilide 
• 589-09-3 N-allyl-N-phenylamine 
• 2454-29-7 N-(2,3-Dichloro-propyl)-4-methyl-N-phenyl-benzenesulfonamide 

Relevant academic research and scientific papers

Ligand-Controlled Regiodivergence for Catalytic Stereoselective Semireduction of Allenamides

Ligand-controlled regiodivergence has been developed for catalytic semireduction of allenamides with excellent chemo- and stereocontrol. This system also provides an example of catalytic regiodivergent semireduction of allenes for the first time. The divergence of the semireduction is enabled by ligand switch with the same palladium pre-catalyst under operationally simple and mild conditions. Monodentate ligand XPhos exclusively promotes selective 1,2-semireduction to afford allylic amides, while bidentate ligand BINAP completely switched the regioselectivity to 2,3-semireduction, producing (E)-enamide derivatives.

Palladium(II)-catalyzed aerobic intramolecular allylic C[sbnd]H activation for the synthesis of indolines

A method for the preparation of indolines via palladium-catalyzed aerobic intramolecular allylic C[sbnd]H activation was developed. Oxygen was successfully used as oxidant with catalytic amount of 1,4-benzoquinone. 16 examples were reported, the majority of substrates gave moderate to good yields.

Palladium-Catalyzed cascade sp2 c?H bond functionalizations allowing one-Pot access to 4?Aryl-1,2,3,4-tetrahydroquinolines from n?Allyl?N?arylsulfonamides

We have developed a palladium-catalyzed cascade reaction allowing an efficient synthesis of 4-aryl-1,2,3,4-tetrahydroquinolines from N-allyl-N-arylsulfonamides and benzenesulfonyl chlorides. In this transformation, two C(sp2)?C(sp3) bonds were formed via activation of C(sp2)?H bonds. The reaction proceeds using the easily accessible catalyst PdCl2, with Li2CO3 as inexpensive base and CuBr as additive, and tolerates a wide variety of substituents on both reaction partners.

Ligand Control of E/Z Selectivity in Nickel-Catalyzed Transfer Hydrogenative Alkyne Semireduction

A nickel-catalyzed transfer hydrogenative alkyne semireduction protocol that can be applied to both internal and terminal alkynes using formic acid and Zn as the terminal reductants has been developed. In the case of internal alkynes, the (E)- or (Z)-olefin isomer can be accessed selectively under the same reaction conditions by judicious inclusion of a triphos ligand.

Palladium-Catalyzed Allylic Amination of Homoallylic Alcohols with Amines via Carbon-Carbon Bond Cleavage

An efficient approach for palladium(II) acetate catalyzed allylic amination of homoallylic alcohols with various amines via sequential retro-allylation and amination was developed, which afforded the corresponding allylic amines in up to 98% yield.

Synthesis of highly substituted dibenzoazocine derivatives by the aza-Claisen rearrangement and intramolecular Heck reaction via 8-exo-trig mode of cyclization

The synthesis of highly substituted dibenzo-azocine systems is still lacking. An efficient synthetic protocol utilizing the sequential aromatic aza-Claisen rearrangement followed by the implementation of the intramolecular Heck reaction as a key step has been developed for the synthesis of various dibenzo-azocine derivatives of biological relevance.

Palladium-catalyzed aminoallylation of activated olefins with allylic halides and phthalimide

The three-component aminoallylation reaction of the activated olefins 2 with the phthalimide 1a and allyl chloride proceeded very smoothly in the presence of Pd2dba3·CHCl3 (5 mol %)/P(4-FC6H4)3 (40 mol %) and Cs2CO3 (3 equiv against 2) in dichloromethane at room temperature to give the corresponding aminoallylated products, N-pent-4-enylphthalimides 3, in 58-99% yields. The reaction of oxazolidinone 1b also proceeded very smoothly to give N-(2,2-dicyano-1-phenylpent-4-enyl)-oxazolidinone in a quantitative yield; however, the Tsuji-Trost-type allylation products 4 were obtained in the case of dibenzylamine, N-tosylaniline, and pyrrolidin-2-one. Further, 2 underwent cycloaddition with N-tosylvinylaziridine 9a in the presence of Pd2dba3·CHCl3 (5 mol %)/P(4-FC6H4)3 (40 mol %) in THF at room temperature, giving the corresponding pyrrolidines 11 in 69-99% yields.