Related Experiment Video
Updated: Jul 11, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Photosensitized [2 + 2]-Cycloadditions of Dioxaborole: Reactivity Enabled by Boron Ring Constraint Strategy
1Department of Chemistry, Indiana University, 800 E. Kirkwood Ave., Bloomington, Indiana 47405, United States.
Abstract:
A strategy to achieve photosensitized [2 + 2] cycloadditions by means of temporary ring constraint is reported. Specifically, a dioxaborole is prepared that undergoes [2 + 2] cycloadditions with a wide variety of alkenes. This strategy overcomes some challenges with the cycloaddition of acyclic substrates. The products can be easily transformed into cyclobutyl diols or 1,4-dicarbonyl compounds; the latter represents a formal alkene vicinal diacylation. The synthetic utility of this method is shown in the synthesis of valuable heterocycles and biatriosporin D.
Related Concept Videos
Cycloaddition Reactions: MO Requirements for Thermal Activation
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Hydroboration-Oxidation of Alkenes
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
