Related Experiment Video
Updated: May 23, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Oxidation-induced nucleophilic substitution at the electron-rich B(12) vertex in [CB11H12]- under catalyst-free
Wanqi Sun1, Yujie Jin1,2, Yongtao Wang1,2
1Department of Chemistry, Zhejiang University 866 Yuhangtang Rd Hangzhou 310058 China wyongtao@zju.edu.cn lihr@zju.edu.cn.
Abstract:
Highly regioselective B(12) substitutions of the monocarborane anion [CB11H12]- has been a challenge. Here, we synthesized a stable B-O-N zwitterionic compound with an impressive yield (isolated yield up to 98%) and excellent regioselectivity at the B(12) position under catalyst-free conditions. The kinetics, substituent effect, and capture experiments are paired with theoretical calculations, showing that the reaction mechanism is oxidation-induced nucleophilic substitution. The hydride anion at the B(12) position is abstracted by an oxoammonium oxidant with lower cleavage energy of 4.2 kcal mol-1 than B(7-11) positions, thereby changing the electronegativity upon the conversion of [CB11H12]- to neutral [CB11H11], in turn giving very high regioselectivity for nucleophilic substitution. This work presents an effective method for synthesizing B(12) oxygen derivatives of the [CB11H12]- anion.
More Related Videos
Related Concept Videos
Carbocations
Nucleophilic Aromatic Substitution: Elimination–Addition
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...
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Hydroboration-Oxidation of Alkenes
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

