Related Experiment Video
Updated: Aug 26, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Convenient access to alkenylated indolo[2,1-a]isoquinolines via palladium-catalyzed cascade Heck cyclization/carbene
Xingyu Yuan1, Yamin Dong1, Yuhang Wang1
1Inner Mongolia Key Laboratory of Synthesis and Application of Organic Functional Molecules, Department of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, 010021, China. shufengchen@imu.edu.cn.
Abstract:
A palladium-catalyzed cascade reaction of N-acryloyl indoles with hydrazones has been developed for the synthesis of alkenylated indolo[2,1-a]isoquinolines. This transformation proceeds through an intramolecular Heck cyclization followed by carbene capture, migratory insertion, and β-hydride elimination. Broad substrate compatibility was demonstrated for both hydrazones and N-acryloyl indoles, affording the desired products in moderate to excellent yields.
More Related Videos
Related Concept Videos
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

