113122-86-4

Upstream product

• 29626-90-2 1-chloro-2-phenylethyl phenyl sulfoxide 
• 100-46-9 benzylamine 
• 7681-84-7 tetrahydrofuran-2-carbaldehyde 
• 66310-10-9 N-benzyl-2,4,6-triphenylpyridinium tetrafluoroborate 
• 109-99-9 tetrahydrofuran 
• 103-80-0 phenylacetyl chloride 
• 113122-76-2 2-[3-(3-Benzenesulfinyl-3-benzyl-oxiranyl)-propoxy]-tetrahydro-pyran 

Downstream Products

• 1283119-68-5 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-6-(tetrahydrofuran-2-yl)-3,4-dihydropyrimidin-2(1H)-one 

Relevant academic research and scientific papers

Photocatalytic α-Acylation of Ethers

Direct coupling of ethers and acyl halides was promoted by a binary catalytic system comprising an Ir-based photocatalyst and a Ni complex under blue-light irradiation. Photocatalysts with high triplet energy directed the catalysis, and the reaction likely proceeded by triplet-triplet energy transfer from the excited photocatalysts. Chlorine radicals generated from an excited Ni complex bearing a Ni-Cl bond would be responsible for generating α-oxy radicals leading to the α-acylated ethers.

C-H Alkylation of Aldehydes by Merging TBADT Hydrogen Atom Transfer with Nickel Catalysis

Catalyst controlled site-selective C-H functionalization is a challenging but powerful tool in organic synthesis. Polarity-matched and sterically controlled hydrogen atom transfer (HAT) provides an excellent opportunity for site-selective functionalization. As such, the dual Ni/photoredox system was successfully employed to generate acyl radicals from aldehydes via selective formyl C-H activation and subsequently cross-coupled to generate ketones, a ubiquitous structural motif present in the vast majority of natural and bioactive molecules. However, only a handful of examples that are constrained to the use of aryl halides are developed. Given the wide availability of amines, we developed a cross-coupling reaction via C-N bond cleavage using the economic nickel and TBADT catalyst for the first time. A range of alkyl and aryl aldehydes were cross-coupled with benzylic and allylic pyridinium salts to afford ketones with a broad spectrum of functional group tolerance. High regioselectivity toward formyl C-H bonds even in the presence of α-methylene carbonyl or α-amino/oxy methylene was obtained.

A Novel Synthesis of 2-Acyl Cyclic Ethers and 3-Keto Cyclic Ethers Including Spiro Cyclic Ethers via Intramolecular Ring-Opening of α,β-Epoxy Sulfoxides with Hydroxyl Group

The α,β-epoxy sulfoxides 1 and 2 bearing a ω-oxyalkyl group were synthesized from ω-oxyalkyl carbonyl compounds and 1-chloroalkyl phenyl sulfoxide.The intramolecular ring opening of the oxirane ring of these α,β-epoxy sulfoxides, through an attack of the terminal hydroxyl group, gave 2-acyl cyclic ethers or 3-keto cyclic ethers, including spiro-type cyclic ethers.This procudure is applicable to the preparation of five- and six-membered cyclic ethers.

INTRAMOLECULAR RING CLOSURE OF α,β-EPOXY SULFOXIDES WITH HYDROXYL GROUP: A NOVEL SYNTHESIS OF 2-ACYL CYCLIC ETHERS AND 3-KETO CYCLIC ETHERS

Exo-trigonal-type intramolecular ring closure of the α,β-epoxy sulfoxides with hydroxyl group gave 2-acyl cyclic ethers (5, 6, and 13 membered rings) in good yields.In contrast to this, endo-trigonal-type ring closure of the α,β-epoxy sulfoxides was rather difficult.