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Reductive Cyclopropanation through Bismuth Photocatalysis.

Shengyang Ni¹, Davide Spinnato¹, Josep Cornella¹

¹Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, Mülheim an der Ruhr, 45470, Germany.

Journal of the American Chemical Society

|August 5, 2024

Summary

This summary is machine-generated.

Researchers developed a novel catalytic method using a low-valent bismuth complex for cyclopropanation reactions under blue LED light. This process involves unique bismuth-based organometallic steps and represents a new reductive photocatalytic approach.

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Area of Science:

Organometallic Chemistry
Photocatalysis
Radical Chemistry

Background:

Cyclopropanation is a vital reaction in organic synthesis.
Developing efficient and sustainable catalytic methods for cyclopropanation remains a key challenge.
Low-valent main group metal complexes are emerging as versatile catalysts.

Purpose of the Study:

To introduce a novel catalytic system for cyclopropanation using a low-valent bismuth complex.
To elucidate the unique organometallic mechanisms involved in the catalytic cycle.
To demonstrate a reductive photocatalytic process driven by blue LED irradiation.

Main Methods:

Development of a low-valent bismuth complex as a catalyst.
Utilizing blue light-emitting diodes (LED) for photocatalysis.
Investigating the reaction mechanism through stoichiometric organometallic experiments.

Main Results:

Successful cyclopropanation of double bonds was achieved under blue LED irradiation.
The catalytic cycle involves unprecedented bismuth-based organometallic steps, including oxidative addition, light-induced homolysis, and reductive termination.
Stoichiometric experiments validated the proposed multi-step reaction mechanism.

Conclusions:

A novel reductive photocatalytic method for cyclopropanation has been established using a low-valent bismuth complex.
The study highlights unique bismuth-centered radical catalysis.
This work expands the scope of photocatalytic transformations mediated by main group elements.