Two C(sp<sup>3</sup>)–F Bond Activation in a CF<sub>3</sub>Group:<i>ipso</i>-Defluorinative Amination Triggered 1,3-Diamination of (Trifluoromethyl)alkenes with Indoles, Carbazoles, Pyrroles, and Sulfonamides
Hao Zeng, Yingying Cai, Huanfeng Jiang, Chuanle Zhu
Abstract
A novel strategy enabled cleavage of two C(sp3)–F bonds in a CF3 group is reported. Triggered by ipso-defluorinative amination, this 1,3-diamination of (trifluoromethyl)alkenes with indoles, carbazoles, pyrroles, and sulfonamides gave acyclic 1,3-diamine products bearing a monofluoroalkene moiety in high yields with good to excellent Z/E selectivities. Preliminary mechanistic studies enable the isolation of the reaction intermediate and indicate that a unique sequential ipso-/γ-selective defluorinative amination pathway is involved in this transformation.
Topics & Concepts
ChemistryAminationTrifluoromethylMoietyBond cleavageMedicinal chemistryFunctional groupCombinatorial chemistryOrganic chemistryCatalysisStereochemistryPolymerAlkylFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsCatalytic C–H Functionalization Methods