Related Experiment Video
Updated: Aug 6, 2026

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)
Published on: January 17, 2020
Mechanistic Insights into Curvature and Coordination-Governed Site-Selectivity in the Multistep Diels-Alder
Wenbo Zhang1,2, Changwei Wang2, Kun Yuan1
1College of Chemical Engineering and Technology, Key Laboratory for New Molecule Materials Design and Function of Gansu Universities, Key Laboratory of Advanced Optoelectronic Functional Materials of Gansu Province, Tianshui Normal University, Tianshui741001, China.
Abstract:
A comprehensive density functional theory study of the Diels-Alder (DA) cycloaddition between cyclopentadiene (Cp) and borospherene B40 is presented, in which the origin of site-selectivity and the feasibility of multistep functionalization are elucidated. By combining a curvature-based descriptor (θp), frontier molecular orbital analysis, and Fukui function calculations, the B[IV,IV] bond is identified as the preferred reactive site. Kinetic and thermodynamic analyses confirm that this site exhibits the lowest activation barrier and the most favorable reaction energy. Activation strain model and energy decomposition analysis further reveal that its superior reactivity arises from an optimal balance between strain and interaction energies. Successive cycloadditions are shown to readily proceed to a tetra-adduct stage. Beyond small-molecule functionalization, B40 is demonstrated to undergo DA-based copolymerization with a bis-anthracene derivative, yielding linear polymers with intrinsic carrier separation. These findings establish borospherene as a versatile platform for selective functionalization and the design of functional materials.
More Related Videos
09:35Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
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 stereochemistry.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Cycloaddition Reactions: Overview
Diels–Alder Reaction: Characteristics of Dienes
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...