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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Acid/Base-Free Acyclic Anionic Oxoborane and Iminoborane Bearing Diboryl Groups
Manling Bao1, Yuyang Dai1, Chunmeng Liu1
1College of Chemistry, Chemical Engineering and Materials Science, School of Radiation Medicine and Protection, Soochow University, Suzhou 215123, P. R. China.
Researchers synthesized novel acid/base-free anionic oxoboranes and neutral iminoboranes. These compounds, isoelectronic to ketones and alkynes, exhibit unique polarized double and triple bonds, expanding the scope of boron chemistry.
Area of Science:
- Organoboron Chemistry
- Inorganic Chemistry
- Synthetic Chemistry
Background:
- Anionic oxoboranes and neutral iminoboranes are isoelectronic analogs of ketones and alkynes, respectively.
- These compounds exhibit unique structures and reactivity, making them attractive research targets.
- Limited availability of acid/base-free examples with diverse characteristics hinders further exploration.
Purpose of the Study:
- To report the first synthesis of acyclic, acid/base-free anionic oxoborane and iminoborane.
- To provide readily accessible examples with diverse electronic and steric properties.
- To characterize the electronic structure and bonding of these novel boron compounds.
Main Methods:
- Synthesis of novel acyclic anionic oxoborane and iminoborane compounds.
- Spectroscopic analysis (e.g., NMR, IR) to confirm structures.
- X-ray crystallography to determine solid-state structures.
- Theoretical calculations (e.g., DFT) to investigate electronic properties and bonding.
Main Results:
- Successful synthesis of acid/base-free acyclic anionic oxoborane (2) and iminoborane (4).
- Characterization reveals a polarized terminal B═O double bond in oxoborane 2.
- Characterization reveals a central B≡N triple bond in iminoborane 4.
- Compounds possess diverse electronic and steric characteristics due to boryl ligands.
Conclusions:
- The study presents the first synthesis of acid/base-free acyclic anionic oxoborane and iminoborane.
- These compounds exhibit unique polarized B═O and B≡N multiple bonds.
- The findings expand the accessibility and diversity of low-coordinate boron compounds for further chemical research.
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