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Coordination Number and Geometry

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For transition metal complexes, the coordination number determines the geometry around the central metal ion. Table 1 compares coordination numbers to molecular geometry. The most common structures of the complexes in coordination compounds are octahedral, tetrahedral, and square planar.

Ethers to Alkyl Halides: Acidic Cleavage

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C–C Bond Cleavage: Retro-Aldol Reaction

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The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
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Coordination Compounds and Nomenclature

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In most main group element compounds, the valence electrons of the isolated atoms combine to form chemical bonds that satisfy the octet rule. For instance, the four valence electrons of carbon overlap with electrons from four hydrogen atoms to form CH4. The one valence electron leaves sodium and adds to the seven valence electrons of chlorine to form the ionic formula unit NaCl (Figure 1a). Transition metals do not normally bond in this fashion. They primarily form coordinate covalent bonds, a...

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Valence Bond Theory

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Coordination compounds and complexes exhibit different colors, geometries, and magnetic behavior, depending on the metal atom/ion and ligands from which they are composed. In an attempt to explain the bonding and structure of coordination complexes, Linus Pauling proposed the valence bond theory, or VBT, using the concepts of hybridization and the overlapping of the atomic orbitals. According to VBT, the central metal atom or ion (Lewis acid) hybridizes to provide empty orbitals of suitable...

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C-Halide bond cleavage by a two-coordinate iron(i) complex.

C G Werncke¹, J Pfeiffer¹, I Müller¹

¹Philipps-University Marburg, Hans-Meerwein-Straße 4, D-35032 Marburg, Germany. gunnar.werncke@chemie.uni-marburg.de.

Dalton Transactions (Cambridge, England : 2003)

|January 15, 2019

Summary

This summary is machine-generated.

This study reveals that a specific iron(I) complex efficiently breaks carbon-halide bonds, including challenging C-F bonds, in Kumada-type cross-coupling reactions. Mechanistic insights suggest a one-electron process involving organoradicals.

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Area of Science:

Organometallic Chemistry
Catalysis
Synthetic Organic Chemistry

Background:

Iron(I) species are implicated as crucial intermediates in Kumada-type C-C cross-coupling catalysis.
The reactivity of well-defined, isolable iron(I) complexes with organohalides remains largely unexplored.

Purpose of the Study:

To investigate the reactivity of a specific two-coordinate iron(I) complex, K{18c6}[Fe(N(SiMe3)2)2], towards various organohalides.
To elucidate the mechanism of carbon-halide bond cleavage mediated by this iron(I) complex.

Main Methods:

Synthesis and characterization of the two-coordinate iron(I) complex.
Reactions with diverse organohalides (including aryl and alkyl halides, and fluoroarenes).
Mechanistic studies involving spectroscopic and computational analyses.

Main Results:

The iron(I) complex demonstrated rapid cleavage of various carbon-halide bonds, notably including robust C-F bonds.
Mechanistic investigations supported a stepwise one-electron transfer pathway.
The formation of intermediate organoradicals was indicated.

Conclusions:

The studied iron(I) complex is highly effective in activating C-X bonds, expanding the scope of iron-catalyzed cross-coupling.
The findings provide valuable insights into the role of iron(I) in organohalide activation and radical generation.
This work paves the way for developing novel iron-based catalytic systems for challenging coupling reactions.