Catalytic Enantioselective Synthesis Enabled by Electrochemistry

Ana Maria Faisca Phillips; Armando J. L. Pombeiro

doi:10.1055/a-2011-7073

Synthesis, Table of Contents

Synthesis 2023; 55(18): 2926-2942
DOI: 10.1055/a-2011-7073

short review

Special Issue Electrochemical Organic Synthesis

Catalytic Enantioselective Synthesis Enabled by Electrochemistry

Ana Maria Faisca Phillips ∗

^aCoordination Chemistry and Catalysis Group, Centro de Química Estrutural, Institute of Molecular Sciences, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais 1, 1049-001 Lisboa, Portugal URL: https://fenix.tecnico.ulisboa.pt/homepage/ist10897

,

Armando J. L. Pombeiro∗

^aCoordination Chemistry and Catalysis Group, Centro de Química Estrutural, Institute of Molecular Sciences, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais 1, 1049-001 Lisboa, Portugal URL: https://fenix.tecnico.ulisboa.pt/homepage/ist10897

^bРeoples’ Friendship University of Russia (RUDN University), Research Institute of Chemistry, Moscow, Russian Federation

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Abstract

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Abstract

Catalytic enantioselective electrochemical synthesis has emerged in recent years as an efficient, clean, sustainable way to obtain chiral, non-racemic molecules. The difficulties in finding reaction conditions that are compatible with the delicate functional groups of many chiral ligands and organocatalysts has hampered the developments in this field. However, the fact that very minute differences in potential can be selected, allows for fine-tuning, so that very high chemoselectivities can be achieved, which is attracting much attention. Although still few in number compared to other areas of knowledge, the existing methods allow a variety of bond-forming reactions to be performed, and very high yields and ees can be achieved. The present review surveys the literature published in the last four years.

1 Introduction

2 Transition-Metal-Catalyzed Reactions

2.1 Alkylation by C–H Bond Functionalization: C(sp³)–C(sp³) Bond Formation

2.2 C(sp³)–C(sp²) Bond Formation

2.2.1 Alkene Functionalization by Cross-Coupling Reactions

2.2.2 Arylation by Cross-Coupling Reactions

2.3 Alkynylation: C(sp³)–C(sp) Bond Formation

2.4 Cross-Coupling Reactions for the Synthesis of Axially Chiral Biaryls

2.5 Cyanofunctionalization

2.6 Miscellaneous

3 Organocatalysis

4 Conclusions

Key words

electrosynthesis - asymmetric synthesis - chirality - anodic oxidation - cathodic reduction - electrolysis - homogeneous catalysis - radicals

Full Text

References

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