Maloney, T. Parker; Dohoda, Alexander F.; Zhu, Alec C.; Michael, Forrest E. published an article in 2022. The article was titled 《Stereoretentive and regioselective selenium-catalyzed intermolecular propargylic C-H amination of alkynes》, and you may find the article in Chemical Science.Formula: C7H9NO2S The information in the text is summarized as follows:
Herein, an intermol. propargylic C-H amination of alkynes was reported. This reaction was operationally convenient and required no transition metal catalysts or additives. Terminal, silyl, and internal alkynes bearing a wide range of functional groups can be aminated in high yields. The regioselectivity of amination for unsym. internal alkynes was strongly influenced by substitution pattern (tertiary > secondary > primary) and by relatively remote heteroat. substituents. The amination of alkynes bearing α-stereocenters occurring with retention of configuration at the newly-formed C-N bond was demonstrated. Competition experiments between alkynes, kinetic isotope effects, and DFT calculations were performed to confirm the mechanistic hypothesis that initial ene reaction of a selenium bis(imide) species is the rate- and product-determining step. This ene reaction has a transition state that results in substantial partial pos. charge development at the carbon atom closer to the amination position. Inductive and/or hyperconjugative stabilization or destabilization of this pos. charge explains the observed regioselectivities. In the experimental materials used by the author, we found 4-Methylbenzenesulfonamide(cas: 70-55-3Formula: C7H9NO2S)
4-Methylbenzenesulfonamide(cas: 70-55-3) belongs to anime. Primary amines having a tertiary alkyl group (R3CNH2) are difficult to prepare with most methods but are made industrially by the Ritter reaction. In this method a tertiary alcohol reacts with hydrogen cyanide (HCN) in the presence of a concentrated strong acid; a formamide, RNH―CHO, is formed first, which then undergoes hydrolysis.Formula: C7H9NO2S
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics