Planar chiral 2-(trifluoromethyl)quinoline-fused ferrocenes via palladium(0)-catalyzed C-H functionalization of trifluoroacetimidoyl chlorides

Transition-metal-catalyzed remote C–H functionalization of thioethers

“…In the past ten years, directing group assisted palladium-catalyzed asymmetric C–H bond functionalization has attracted considerable attention. 28 Very recently, Shi and co-workers developed a palladium-catalyzed and thioether-directed atroposelective C–H olefination by employing a novel chiral spiro phosphoric acid ligand SPA ( Scheme 19a ). 29 More than 69 examples of axially chiral styrenes with a conjugated 1,3-diene scaffolds were obtained in good yields (up to 99% yields) with excellent enantioselectivities (up to 99% ee) and complete Z -selectivity control.…”

Synthesis and Applications of Ferrocene‐Fused Nitrogen Heterocycles

“…Building upon previous work by Cramer and Grosheva on the enantioselective synthesis of 1H-isoindoles through Pdcatalyzed CÀ H functionalization using trifluoroacetimidoyl chlorides as electrophilic components, [42] very recently, Liu and co-workers reported the catalytic enantioselective synthesis of planar chiral 2-(trifluoromethyl)quinoline fused ferrocenes through Pd-catalyzed intramolecular CÀ H imidoylation (Scheme 15). [43] Chiral sulfonamide phosphine ligands proved to be critical, providing high yields and enantioselectivities (up to 95 % ee).…”

Controllable access to trifluoromethyl-containing indoles and indolines: palladium-catalyzed regioselective functionalization of unactivated alkenes with trifluoroacetimidoyl chlorides

“… 10 Our group and others have developed a variety of synthetic methods for preparing various trifluoromethyl-containing N-heterocycles by the employment of trifluoroacetimidoyl chlorides as reactive partners. 11 When the halogen atom was located at the ortho position of the aryl moiety of trifluoroacetimidoyl chloride, it will serve as a 4-atom reaction precursor with two electrophilic reactive sites, which can be adopted as useful building blocks to construct trifluoromethyl-substituted N-heterocycles. For instance, Zhu, Chen and co-workers demonstrated a palladium-catalyzed directed C-2 and C-3 dual C–H functionalization of N -(2-pyrimidyl)-indoles with trifluoroacetimidoyl chlorides for accessing fluorinated isocryptolepine analogues.…”