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Alkenyl Magnesium Compounds: Generation and Synthetic Application.

Miaomiao Zhu^1,2, Liang Liu¹, 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, P. R. China.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|July 10, 2018

Summary

This review covers three types of reactive alkenyl magnesium compounds, including Grignard reagents, carbenoids, and magnesacarbocycles. These compounds are synthesized via various magnesium exchange and catalytic methods for diverse synthetic applications.

Keywords:

Grignard reagents carbenoids carbocycles magnesium transmetalation

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Area of Science:

Organic Chemistry
Organometallic Chemistry

Background:

Alkenyl magnesium compounds exhibit high reactivity, making them valuable in organic synthesis.
These compounds feature a crucial [Mg-C=C] fragment, enabling diverse chemical transformations.

Purpose of the Study:

To review and categorize three main types of alkenyl magnesium compounds.
To highlight their synthesis methods and subsequent reactions and applications.

Main Methods:

Halogen-magnesium exchange reactions for preparing alkenyl Grignard reagents and alkenyl magnesium carbenoids.
Sulfoxide-magnesium exchange reactions for alkenyl magnesium carbenoids.
Zirconium- or titanium-catalyzed cyclomagnesation and transmetalation for magnesacarbocycles.

Main Results:

Detailed summary of alkenyl Grignard reagents, alkenyl magnesium carbenoids, and magnesacarbocycles.
Exploration of the synthetic pathways and reactivity of these organomagnesium species.
Presentation of various applications stemming from these compounds in organic synthesis.

Conclusions:

Alkenyl magnesium compounds are versatile reagents in modern synthetic chemistry.
The reviewed methods provide efficient access to these reactive intermediates.
Their diverse applications underscore their importance in constructing complex organic molecules.