Related Experiment Video
Updated: Sep 2, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Catalytic asymmetric propargylic substitution enabled by remote leaving groups
Jia-Jun Qiao1, Yi-Ming Ma1, Zhi-Tao He1,2,3,4
1State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai, 200032, China. hezt@sioc.ac.cn.
Abstract:
Propargylic substitution is a basic transformation model in organic synthesis, which requires the adoption of alkyne substrates bearing a vicinal leaving group. Recently, the exploration of remote-leaving-group-promoted propargylic substitution pioneered by Fang, He and Xu, has gained much attention and provided new possibilities for this classical area. With this design, a series of related studies have been reported and enabled the enantioselective construction of diverse privileged skeletons. This review article provides a detailed summary of the origin, development, mechanisms, limitations and future directions of this nonclassical propargylation model.
Related Concept Videos
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between the...
Radical Substitution: Allylic Bromination
Leaving Groups
In general, in a nucleophilic substitution reaction, a nucleophile displaces a functional group, called the leaving group, from the substrate to give a substituted product. A leaving group departs the substrate molecule through heterolytic cleavage, taking the pair of electrons with it to become a relatively stable weak base in the form of an anion or a neutral molecule.
In a nucleophilic...
Preparation of Alcohols via Substitution Reactions
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
Regioselectivity of Electrophilic Additions-Peroxide Effect
Nucleophilic Aromatic Substitution: Elimination–Addition

