Related Experiment Video
Updated: Aug 11, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Steric and electronic effects of arsa-Buchwald ligands on Suzuki-Miyaura coupling reaction
Akifumi Sumida1, Kenta Ogawa1, Hiroaki Imoto1
1Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Goshokaido-cho, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan. himoto@kit.ac.jp.
Abstract:
The Suzuki-Miyaura coupling (SMC) reaction is one of the most commonly used cross-coupling reactions. Bulky biaryldialkyl monophosphine ligands, i.e., Buchwald ligands, are beneficial for the SMC reaction. We recently developed a synthetic procedure for arsa-Buchwald ligands, arsenic analogs of Buchwald ligands, and found that these ligands are effective for sterically hindered substrates because of facilitating the transmetalation step owing to the longer arsenic-palladium bond. However, the relationship between the structure and steric/electronic properties of the arsa-Buchwald ligands has not yet been studied in detail. In this study, a series of arsa-Buchwald ligands with various alkyl substituents were synthesized. The cyclopentyl group afforded the highest catalytic activity for the SMC reaction, particularly with sterically hindered substrates. Furthermore, the steric/electronic properties of the arsa-Buchwald ligands were computationally analyzed.
More Related Videos
19:58Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
12:08Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
Published on: June 24, 2022
Related Concept Videos
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...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Directing and Steric Effects in Disubstituted Benzene Derivatives
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
¹H NMR: Long-Range Coupling
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...