Related Experiment Video
Updated: Sep 6, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Conformational Flexibility as a Tool for Enabling Site-Selective Functionalization of Unactivated sp C-O Bonds in
Ciro Romano1, Laura Talavera1,2, Enrique Gómez-Bengoa3
1Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain.
Abstract:
A dual catalytic manifold that enables site-selective functionalization of unactivated sp C-O bonds in cyclic acetals with aryl and alkyl halides is reported. The reaction is triggered by an appropriate σ*-p orbital overlap prior to sp C-O cleavage, thus highlighting the importance of conformational flexibility in both reactivity and site selectivity. The protocol is characterized by its excellent chemoselectivity profile, thus offering new vistas for activating strong σ sp C-O linkages.
Related Concept Videos
Acid-Catalyzed Ring-Opening of Epoxides
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Cycloaddition Reactions: Overview
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
