Related Experiment Video
Updated: Sep 29, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Radical boron migration of allylboronic esters
Xiangzhang Tao1, Shengyang Ni1, Lingyu Kong1
1State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University Nanjing 210023 China yiwang@nju.edu.cn.
This study introduces a new photocatalyzed reaction for allylboronic esters, enabling boron atom migration across the carbon skeleton. This process efficiently creates functionalized alkyl boronates with diverse applications.
Area of Science:
- Organic Chemistry
- Organoboron Chemistry
- Photocatalysis
Background:
- Allylboronic esters are versatile synthetic intermediates.
- Controlling boron atom migration is crucial for synthesizing complex organoboron compounds.
Purpose of the Study:
- To develop a novel photocatalyzed method for 1,3-boron migration in allylboronic esters.
- To explore the scope and limitations of this new synthetic transformation.
Main Methods:
- Photocatalysis was employed to initiate the boron migration.
- The reaction mechanism involves consecutive 1,2-boron migrations and a Smiles-type rearrangement.
Main Results:
- A variety of terminally functionalized alkyl boronates were synthesized.
- The reaction tolerates migrating heteronuclei radicals and dearomatization processes.
- This enables the construction of highly functionalized boron-containing frameworks.
Conclusions:
- The reported photocatalyzed 1,3-boron shift offers an efficient route to functionalized alkyl boronates.
- This method expands the synthetic utility of organoboron compounds in organic synthesis.
Related Concept Videos
Radical Substitution: Allylic Bromination
Hydroboration-Oxidation of Alkenes
π Molecular Orbitals of the Allyl Radical
The allyl systems have identical molecular orbitals but differ in the number of π electrons....
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...
Radical Anti-Markovnikov Addition to Alkenes: Overview
Radical Reactivity: Electrophilic Radicals

