98528-33-7

Upstream product

• 93406-12-3 N-benzoyl-4-phenylbutylamine 
• 93816-73-0 N-(4-Phenyl-3-butenyl)benzamide 
• 3389-54-6 n-benzoylpyrrolidine 
• 591-50-4 iodobenzene 

Relevant academic research and scientific papers

Visible light bromide catalysis for oxazoline, pyrrolidine, and dihydrooxazine synthesesviaCsp3-H functionalizations

A catalytic benzylic Csp3-H functionalization protocol is described here. This visible light-mediated process is centered on the utilization of a bromide catalyst and oxidant to generate a nitrogen (N)-centered radical for a site-selective hydrogen atom transfer (HAT) process. This strategy enabled the unconventional syntheses of a number of N-heterocycles dependent on the amide identity. We also discovered a nucleophilicity-dependent kinetic resolution for stereochemical differentiation of Csp3-H bonds that enabled the stereoselective synthesis ofcis- andtrans-oxazolines.

Remote Radical Desaturation of Unactivated C?H Bonds in Amides

Desaturation of inert aliphatic C?H bonds in alkanes to form the corresponding alkenes is challenging. In this communication, a new and practical strategy for remote site-selective desaturation of amides via radical chemistry is reported. The readily installed N-allylsulfonylamide moiety serves as an N radical precursor. Intramolecular 1,5-hydrogen atom transfer from an inert C?H bond to the N-radical generates a translocated C-radical which is subsequently oxidized and deprotonated to give the corresponding alkene. The commercially available methanesulfonyl chloride is used as reagent and a Cu/Ag-couple as oxidant. The remote desaturation is realized on different types of unactivated sp3-C?H bonds. The potential synthetic utility of this method is further demonstrated by the dehydrogenation of natural product derivatives and drugs.

Electrochemical-Oxidation-Induced Site-Selective Intramolecular C(sp3)-H Amination

The cross-coupling of C(sp3)-H and N-H represents one of the most straightforward approaches to construct saturated nitrogen-containing compounds. The additional oxidants or halogenated reagents are generally required in such processes. Herein,

Calcium(II)-Catalyzed Intra- and Intermolecular Hydroamidation of Unactivated Alkenes in Hexafluoroisopropanol

A combination of a calcium(II) triflimide salt and hexafluoroisopropanol (HFIP) was found to be a highly efficient promoter system for the intra- and intermolecular hydroamidation of unactivated alkenes. Unlike other methods, a vast array of functional groups is tolerated at the nitrogen and alkene moieties. The reaction produces the corresponding nitrogen-containing compounds in excellent yields and good diastereoselectivities. The use of HFIP as solvent proved crucial for the proper carrying out of this transformation. Its role, as well as that of calcium and its NTf2 ligand, was rationalized by DFT computations. These calculations show how the [(NTf2)Ca(HFIP)n]+ complex can activate the amide via a basic site of the NTf2 ligand and the alkene with one acidic HFIP proton. The acidity of HFIP is exacerbated by the coordination to the calcium center, the more so as n increases.

Selective and catalytic arylation of N-phenylpyrrolidine: sp3 C-H bond functionalization in the absence of a directing group

We herein describe our studies on arylation of N-phenylpyrrolidine, which led to the development of a new transformation for the direct and selective arylation of sp3 C-H bonds in the absence of a directing group. In this method, Ru(H)2(CO)(PCy3)3 4 was used as the catalyst, and preliminary mechanistic studies suggested that Ru(Ph)(I)(CO)(PCy3)2 5 is the key intermediate of the catalytic cycle. A large kinetic isotope effect (kH/kD = 5.4) was observed, which supports the proposal that C-H bond metalation is the slow step. Preliminary examination of the substrate scope showed that in addition to N-phenylpyrrolidine, N-methyl- and N-benzylpyrrolidine, as well as N-benzoylpyrrolidine, were arylated under the reaction conditions. Copyright

Anchimeric assistance in hydrogen-atom transfer to bromine

The free-radical benzylic brominations of series of phenylalanine derivatives and O-phenylalkyi benzoates and N-phenylalkylamides with N-bromosuccinimide exhibit anchimeric assistance by neighbouring ester and amido groups. Rate enhancement occurs through