Flow Chemistry of Metal Carbenoid Species towards Selective Organic Synthesis

Abstract

This review deals with C1 carbenoid chemistry, with a focus on lithium carbenoid species generated in flash flow systems. Strict control of the temperature, residence time, and mixing efficiency has led to various transformation reactions involving epoxidation, cyclopropanation, and homologation, among others. The use of other metal species, including trifluoromethylpotassium (CF₃K) and magnesium/ zinc carbenoids, in flow systems is also introduced.

1 Introduction

1.1 Lithium Carbenoids in C1 Chemistry

1.2 Flow Chemistry for C1 Lithium Carbenoids

2 Flow Reactions Involving Carbenoid Species

2.1 Deprotonative Generation of Lithium Carbenoid Species

2.2 Generation of Lithium Carbenoid Species via Halogen–Lithium Exchange

2.3 Generation of Lithium Carbenoid Species via Reductive Lithiation

2.4 Generation of Lithium Carbenoid Species via Alkyllithiation

2.5 Generation of Trifluoromethylpotassium Species in Flow

2.6 Generation of Other Metal Carbenoid Species

3 Conclusion

Key words

flow chemistry - carbenoids - C1 chemistry - flash chemistry - organometallic reagents

Publication History

Received: 27 February 2024

Accepted after revision: 09 April 2024

Accepted Manuscript online:
09 April 2024

Article published online:
24 April 2024

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