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Updated: Mar 15, 2026

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Dialkylboron guanidinates: syntheses, structures and carbodiimide de-insertion reactions
Antonio Antiñolo1, Fernando Carrillo-Hermosilla, Rafael Fernández-Galán
1Centro de Innovación en Química Avanzada (ORFEO-CINQA), Departamento de Química Inorgánica, Orgánica y Bioquímica, Facultad de Ciencias y Tecnologías Químicas, Universidad de Castilla-La Mancha, Campus Universitario, E-13071 Ciudad Real, Spain. Antonio.Antinolo@uclm.es.
Novel dialkylboron guanidinate compounds were synthesized and characterized. These compounds exhibit unique coordination and undergo reversible reactions with aminoboranes and carbodiimides, offering insights into boron-nitrogen chemistry.
Area of Science:
- Organometallic Chemistry
- Boron Chemistry
- Coordination Chemistry
Background:
- Guanidinate ligands are versatile in coordinating with metal and main group elements.
- Dialkylboron compounds are important in synthesis and catalysis.
- Understanding the reactivity and stability of boron-guanidinate complexes is crucial.
Purpose of the Study:
- To synthesize and characterize novel symmetrical and asymmetrical dialkylboron guanidinate compounds.
- To investigate the structural features and coordination modes of these new compounds.
- To study the equilibrium and kinetic behavior of these compounds with aminoboranes and carbodiimides.
Main Methods:
- Synthesis via salt metathesis reaction between lithium guanidinates and chloroboranes.
- Structural characterization using X-ray diffraction.
- Equilibrium and kinetic studies to determine thermodynamic and activation parameters.
Main Results:
- Successful synthesis of various symmetrical and asymmetrical dialkylboron guanidinates.
- X-ray diffraction confirmed chelate coordination of guanidinate ligands and additional boron attachments.
- Compounds 1-4 showed slow equilibrium with aminoboranes and carbodiimides at 25 °C, while compounds 5-8 required higher temperatures for similar reactions.
Conclusions:
- The study reports a new class of dialkylboron guanidinate compounds with diverse structures.
- The coordination chemistry and reactivity, including reversible carbodiimide de-insertion, have been elucidated.
- The findings contribute to the understanding of boron-nitrogen bonding and reactivity.
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