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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

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Published on: August 16, 2018

Decarboxylative alkenylation.

Jacob T Edwards¹, Rohan R Merchant¹, Kyle S McClymont¹

¹Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

|April 21, 2017

Summary

This summary is machine-generated.

This study introduces a novel method for synthesizing olefins of any pattern or geometry from readily available alkyl carboxylic acids. This approach utilizes catalytic carbon dioxide extrusion and organozinc coupling, simplifying olefin synthesis and natural product preparation.

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Area of Science:

Organic Chemistry
Synthetic Methodology
Catalysis

Background:

Olefin chemistry is crucial for organic matter manipulation but relies on outdated synthetic methods.
Existing olefin synthesis techniques, including metathesis, are often limited or were developed decades ago.
Alkyl carboxylic acids are abundant and versatile chemical building blocks.

Purpose of the Study:

To develop a simple and broadly applicable method for synthesizing olefins with diverse substitution patterns and geometries.
To leverage the activating principles of amide-bond synthesis for carboxylic acid functionalization.
To provide an economical and scalable route for olefin preparation from carboxylic acids.

Main Methods:

Utilized nickel- or iron-based catalysis to activate alkyl carboxylic acids.
Employed principles from amide-bond synthesis to facilitate carbon dioxide extrusion.
Coupled the activated carboxylic acid derivative with organozinc reagents to form olefins.

Main Results:

Successfully synthesized over 60 diverse olefins across various substrate classes.
Demonstrated the method's ability to control olefin geometry and substitution patterns.
Streamlined retrosynthetic analysis, exemplified by the synthesis of 16 natural products from 10 families.

Conclusions:

Presented a new, efficient, and versatile method for olefin synthesis directly from alkyl carboxylic acids.
The catalytic process offers an economical and scalable alternative to existing olefin synthesis strategies.
This methodology significantly simplifies the preparation of complex molecules, including natural products.