Related Experiment Video
Updated: Apr 25, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Boronyl Radical-Catalyzed Intermolecular (4 + 2) Cycloaddition of Cyclobutanes and Alkenes: Synthesis of
Min Zhao1, Zhengwei Ding2, Saima Perveen3
1Frontier Institute of Science and Technology and Interdisciplinary Research Centre of Frontier Science and Technology, Xi'an Jiaotong University, Xi'an, Shaanxi 710049, China.
Abstract:
The cyclohexane skeleton is ubiquitous in small-molecule drugs and bioactive natural products. However, there remains a lack of synthetic methods for polysubstituted cyclohexanes that simultaneously satisfy the requirements of readily available starting materials, high atom economy, and low-cost catalysts, which to a certain extent limits the application of this type of skeleton in the field of drug research and development. Herein, we report the first example of a boron radical-catalyzed intermolecular (4 + 2) cycloaddition reaction between cyclobutanes and alkenes, a strategy that provides an efficient and general method for the synthesis of polysubstituted cyclohexanes. This reaction exhibits broad substrate scope, being compatible with monosubstituted, 1,1-disubstituted, and trisubstituted alkenes and can selectively construct tri-, tetra-, and pentasubstituted cyclohexane derivatives in moderate-to-excellent yields.
More Related Videos
09:35Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
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
Hydroboration-Oxidation of Alkenes
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.
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.
Cycloaddition Reactions: MO Requirements for Thermal Activation
Cycloaddition Reactions: Overview
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...