Zhang, Xue; Ling, Liang; Luo, Meiming; Zeng, Xiaoming published the artcile< Accessing Difluoromethylated and Trifluoromethylated cis-Cycloalkanes and Saturated Heterocycles: Preferential Hydrogen Addition to the Substitution Sites for Dearomatization>, Name: 3-(Trifluoromethyl)pyridine, the main research area is difluoromethyl cis cycloalkane saturated heterocycle diastereoselective preparation; arene heteroarene cycloalkyl amino carbene rhodium catalyst dearomative reduction; trifluoromethyl cis cycloalkane saturated heterocycle diastereoselective preparation; heteroarene arene cycloalkyl amino carbene rhodium catalyst dearomative reduction; N-heterocyclic carbenes; fluorine; hydrogenation; reduction; rhodium.
A straightforward process in which a cyclic (alkyl)(amino)carbene/Rh catalyst system facilitates preferential addition of hydrogen to substitution sites of difluoromethylated and trifluoromethylated arenes and heteroarenes, leading to dearomative reduction was reported. This strategy enabled diastereoselective synthesis of cis-difluoromethylated and cis-trifluoromethylated cycloalkanes such as I [R = 2-COMe, 4-pyrazolyl, 3-OTBS, etc.; R1 = CF2H, CF3] and saturated heterocycles, e.g. II, and even allowed formation of all-cis multi-trifluoromethylated cyclic products with a defined equatorial orientation of the di- and trifluoromethyl groups. Deuterium-labeling studies indicated that hydrogen preferentially attacked substitution sites of planar arenes, resulting in dearomatization, possibly with heterogeneous Rh as reactive species, followed by either reversible or irreversible hydrogen addition to nonsubstitution sites.
Angewandte Chemie, International Edition published new progress about Aromatic compounds Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 3796-23-4 belongs to class pyridine-derivatives, and the molecular formula is C6H4F3N, Name: 3-(Trifluoromethyl)pyridine.