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Structural Isomerism

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Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
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Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Published on: February 6, 2019

Organocopper(III) Spiro Complexes: Synthesis, Structural Characterization, and Redox Transformation.

Liang Liu¹, Miaomiao Zhu^1,2, Hai-Tao Yu²

¹Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University , Beijing 100871, China.

Journal of the American Chemical Society

|September 22, 2017

Summary

This study provides the first concrete evidence for copper(III) intermediates in C-C bond formation. Novel copper(III) spiro complexes were synthesized and demonstrated intramolecular reductive elimination, confirming their role in catalysis.

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Area of Science:

Organometallic Chemistry
Catalysis
Synthetic Chemistry

Background:

Reductive elimination of copper(III) intermediates is crucial for C-C and C-heteroatom bond formation.
Direct evidence for these Cu(III) intermediates is lacking due to their instability.

Purpose of the Study:

To synthesize and structurally characterize novel organocopper(III) spiro complexes.
To provide concrete evidence for the involvement of Cu(III) intermediates in reductive elimination reactions.

Main Methods:

Synthesis of novel organocopper(I) and organocopper(III) spiro complexes.
Single-crystal X-ray structural analysis to determine geometries.
Redox titrations to observe interconversion between Cu(I) and Cu(III) states.

Main Results:

Novel organocopper(III) and organocopper(I) spiro complexes were successfully synthesized and structurally characterized.
X-ray analysis revealed distinct geometries: distorted square-planar for Cu(III) and tetrahedral for Cu(I).
Experimental observation of redox transformation between Cu(I) and Cu(III) spiro complexes.

Conclusions:

The synthesized organocopper(III) spiro compounds provide the first concrete evidence for Cu(III) intermediates.
These Cu(III) complexes undergo intramolecular reductive elimination to form C-C bonds.
This work validates the proposed mechanism in copper-catalyzed bond formation reactions.