Mechanochemical Synthesis of Iodine-Substituted Bicyclo[1.1.1]pentanes Via a Piezoelectric Catalytic System
Pan Gao1, Kexin Zhai1, Xiangchuan Xiu1
1College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou225002, China.
Abstract:
Iodo-substituted bicyclo[1.1.1]pentanes (iodo-BCPs) are valuable synthetic linchpins for the preparation of diverse BCP-containing bioisosteres. However, existing methods often require photocatalysts, specialized equipment, or large amounts of organic solvents. Herein, we report the first piezocatalytic mechanochemical radical iodination of [1.1.1]propellane (TCP) using recyclable tetragonal tet-BaTiO3 under ball-milling conditions. Mechanical energy promotes single-electron transfer, enabling efficient strain-release functionalization of TCP with pyridyl, benzyl, and α-carbonyl iodides. The protocol proceeds without photocatalysts and exhibits broad substrate scope. Mechanistic studies support a piezocatalytically initiated radical pathway. This sustainable method provides straightforward access to synthetically versatile iodo-BCPs for medicinal chemistry applications.
More Related Videos
09:09A Facile Synthetic Method to Obtain Bismuth Oxyiodide Microspheres Highly Functional for the Photocatalytic Processes of Water Depuration
Published on: March 29, 2019
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Thermal and Photochemical Electrocyclic Reactions: Overview
Pericyclic Reactions: Introduction
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic rearrangements are...
Cationic Chain-Growth Polymerization: Mechanism
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
