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Reductive C-C Coupling from α,β-Unsaturated Nitriles by Intercepting Keteniminates.

Lillian V A Hale¹, N Marianne Sikes¹, Nathaniel K Szymczak¹

¹Department of Chemistry, University of Michigan, 930 N. University, Ann Arbor, MI, 48109, USA.

Angewandte Chemie (International Ed. in English)

|April 25, 2019

Summary

This study introduces a new atom-economic method using hydrogen transfer catalysis to create and use nitrile anion equivalents. This approach enables efficient reductive C-C coupling reactions with α,β-unsaturated nitriles.

Keywords:

hydrogenative acylation keteniminates reductive C−C coupling ruthenium α,β-unsaturated nitriles

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Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Hydrogen transfer catalysis offers an atom-economic approach to chemical synthesis.
Nitrile anion equivalents are valuable synthetic intermediates.
Developing new catalytic methods for C-C bond formation is crucial in organic synthesis.

Purpose of the Study:

To develop an atom-economic strategy for generating and intercepting nitrile anion equivalents.
To explore the use of hydrogen transfer catalysis with α,β-unsaturated nitriles.
To achieve reductive C-C coupling reactions via keteniminate intermediates.

Main Methods:

Utilizing a pincer-based Ruthenium-hydride (Ru-H) complex for catalytic hydride transfer.
Employing α,β-unsaturated nitriles as substrates.
Performing in situ generation of keteniminate intermediates under catalytic hydrogenation conditions.
Electrophilic trapping of keteniminates with anhydrides.

Main Results:

Selective 1,4-hydride transfer to α,β-unsaturated nitriles, forming structurally characterized κ-N-coordinated keteniminates.
Successful in situ generation and electrophilic addition to keteniminates.
High yields of α-cyanoacetates obtained through reductive C-C coupling.

Conclusions:

This work establishes a novel application of hydrogen transfer catalysis for α,β-unsaturated nitriles.
The developed strategy provides an efficient route to α-cyanoacetates via keteniminate intermediates.
The methodology represents a significant advancement in catalytic reductive C-C coupling reactions.