Copper-Catalyzed Intramolecular Olefinic C(sp²)–H Amidation for the Synthesis of <i>γ</i>-Alkylidene-<i>γ</i>-lactams

Herein, we report the copper-catalyzed dehydrogenative C(sp2)–N bond formation of 4-pentenamides via nitrogen-centered radicals. This reaction provides a straightforward and efficient preparation method for γ-alkylidene-γ-lactams. Notably, we could controllably synthesize α,β-unsaturated- or α,β-saturated-γ-alkylidene-γ-lactams depending on the reaction conditions

Copper-Catalyzed sp³ C–H Aminative Cyclization of 2‑Alkyl‑<i>N</i>‑arylbenzamides: An Approach for the Synthesis of <i>N</i>‑Aryl-isoindolinones

The synthesis of isoindolinones via copper-catalyzed sp³ C–H functionalization of 2-alkyl-<i>N</i>-substituted benzamides is described. This process does not require the preparation of halogenated substitutes, expensive transition metals, or toxic Sn or CO gas. This method provides an efficient approach to generate various functionalized isoindolinones

Deprotonative Silylation of Aromatic C–H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride

A method for the deprotonative silylation of aromatic C–H bonds has been developed using trifluoromethyltrimethylsilane (CF₃SiMe₃, Ruppert–Prakash reagent) and a catalytic amount of fluoride. In this reaction, CF₃SiMe₃ is considered to act as a base and a silicon electrophile. This process is highly tolerant to various functional groups on heteroarenes and benzenes. Furthermore, this method can be applied to the synthesis of trimethylsilyl group-containing analogs of TAC-101, which is a bioactive synthetic retinoid with selective affinity for retinoic acid receptor α (RAR-α) binding. We also report further transformations of the silylated products into useful derivatives