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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

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Introduction
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C-C σ-Bond Oxidative Addition and Hydrofunctionalization by a Macrocycle-Supported Diiron Complex.

Tianchang Liu¹, Ryan P Murphy¹, Patrick J Carroll¹

¹Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States.

Journal of the American Chemical Society

|July 26, 2022

Summary

This study demonstrates novel unassisted oxidative addition reactions for C-C bond activation using a diiron complex. These findings enable efficient C-C bond functionalization through catalytic cycles.

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Area of Science:

Organometallic Chemistry
Catalysis
Synthetic Chemistry

Background:

C-C bond activation is crucial for organic synthesis.
Developing new catalytic methods for C-C bond functionalization remains a significant challenge.

Purpose of the Study:

To report the first examples of unassisted C(sp)-C(sp2) and C(sp)-C(sp3) bond oxidative addition reactions.
To explore the catalytic cycles for C-C sigma bond functionalization.

Main Methods:

Utilizing a diiron complex, (3PDI2)Fe2(μ-N2)(PPh3)2 ([Fe2N]), for oxidative addition reactions.
Reacting [Fe2N] with various diphenylacetylenes and phenylalkyne derivatives.
Investigating subsequent hydrofunctionalization reactions with H2 or HBpin.

Main Results:

Achieved unassisted C(sp)-C(sp2) bond oxidative addition with diphenylacetylenes.
Observed selective C(sp)-C(sp2) or C(sp)-C(sp3) bond activation with phenylalkynes based on steric hindrance.
Demonstrated catalytic hydrofunctionalization (hydrogenation and hydroboration) of C-C sigma bonds, regenerating the diiron complex.

Conclusions:

The diiron complex facilitates unprecedented C-C bond oxidative addition reactions.
This work provides a new catalytic pathway for C-C sigma bond functionalization, offering thermodynamically favorable products.