A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions.

Munmun Ghosh,Valmik S Shinde,Magnus Rueping

doi:10.3762/bjoc.15.264

Munmun Ghosh, Valmik S Shinde + Show 1 more

Open Access

https://doi.org/10.3762/bjoc.15.264

Copy DOI

Abstract

The direct exploitation of ‘electrons’ as reagents in synthetic organic transformations is on the verge of a renaissance by virtue of its greenness, sustainability, atom economy, step economy and inherent safety. Achieving stereocontrol in such organic electrochemical reactions remains a major synthetic challenge and hence demands great expertise. This review provides a comprehensive discussion of the details of stereoselective organic electrochemical reactions along with the synthetic accomplishments achieved with these methods.

Highlights

Electric current-assisted exchange of electrons between an electrode and an organic substrate, resulting in desired redox transformation of the substrate via the intermediacy of a highly reactive electrogenerated reagent, is generally termed ‘organic electrochemical reactions’
We aim to focus on methods for achieving stereocontrol in synthetic organic electrochemistry via a systematic description of the reported literature on chiral inductors, followed by their applications in the synthesis of natural products and bioactive compounds including late-stage functionalizations
Having described the research that has been conducted to achieve suitable ‘electrical’ replacements of conventional ‘chemical’ organic transformations, it is clear that the establishment of stereoselective variants of these synthetic operations remains challenging, making the use of electrochemistry to achieve stereoselective transformations an often unsolved problem

Summary

Introduction

Electric current-assisted exchange of electrons between an electrode and an organic substrate, resulting in desired redox transformation of the substrate via the intermediacy of a highly reactive electrogenerated reagent (radical, ion or ionic radical), is generally termed ‘organic electrochemical reactions’. Amidst tremendous effort by synthetic organic chemists towards reaching targets selectively from readily available starting materials using low cost, nontoxic reagents and solvents while maintaining high atom and step economy and minimizing waste production with respect to safety standards, electroorganic chemistry (EOC) stands out as a potential greener and sustainable alternative to traditional redox protocols [1,2,3,4]. Starting from its inception in 1800, EOC has undergone a series of advances with respect to the design of electrochemical cells; the nature of the electrode materials; the applied current or potential; the available redox mediators, electroauxiliaries, supporting electrolyte, types of catalysts; and many other controlling factors [5,6,7].

Objectives

Findings

Conclusion