Related Experiment Video
Updated: Oct 3, 2026

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
Published on: March 20, 2017
Cascade MHAT Radical Cyclopentannulation of Skipped Enyne to Access Highly Functionalized Carbocycles
Santosh J Gharpure1, Simran R Narang1, Rupali S Chavan1
1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
Abstract:
An iron-mediated metal-hydride hydrogen atom transfer (MHAT) radical cyclization cascade has been developed for the efficient construction of highly functionalized carbocyclic frameworks. This versatile [3+2] cyclopentannulation strategy starting from skipped enynes provides rapid access to a broad range of alkylidene cyclopentanes/cyclopentenes. Termination of this cascade with various radical trapping agents allows efficient construction of annulated products via successive C-H/C-C/C-C/C-X bond (X = C, H, S, Se, Te, I) formation. The method allows an expeditious entry into diquinanes, angular triquinanes with 4 quaternary carbons (3 contiguous) and substituted cyclopentadienes, all amenable to complex carbocycle synthesis.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
09:35Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Related Concept Videos
Cycloaddition Reactions: Overview
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group with both...
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Cycloaddition Reactions: MO Requirements for Thermal Activation
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)