Organic Electrosynthesis: Applications in Complex Molecule Synthesis

Shatskiy, Andrey; Lundberg, Helena; Kärkäs, Markus D.

doi:10.1002/celc.201900435

Cited by 160 publications

(105 citation statements)

References 298 publications

(181 reference statements)

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“…Application of organo-electrosynthesis in complex molecule synthesis has recently been reviewed by Lundberg and Kärkäs [106]. In the following section of this review, we describe potential practical applications of asymmetric electroorganic reactions in the synthesis of different complex and biologically relevant compounds as well as natural products.…”

Section: Reviewmentioning

confidence: 99%

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

Ghosh

Shinde

Rueping

2019

Beilstein J. Org. Chem.

149

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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.

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Section: Reviewmentioning

confidence: 99%

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

Ghosh

Shinde

Rueping

2019

Beilstein J. Org. Chem.

149

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“…Reductive dehalogenation is a classic transformation in electrosynthesis [113] that includes stereoselective examples using cobalt catalysis [99,100]. The principle is relevant for transition metal-catalyzed reductive cross-electrophile couplings [114][115][116], and an enantioselective coupling of alkenyl and benzyl halides using a chiral Ni catalyst was demonstrated by Reisman and co-workers under electrochemical conditions [117].…”

Section: Cross-electrophile Couplingsmentioning

confidence: 99%

Recent Advances in Asymmetric Catalytic Electrosynthesis

Margarita

Lundberg

2020

Catalysts

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The renewed interest in electrosynthesis demonstrated by organic chemists in the last years has allowed for rapid development of new methodologies. In this review, advances in enantioselective electrosynthesis that rely on catalytic amounts of organic or metal-based chiral mediators are highlighted with focus on the most recent developments up to July 2020. Examples of C-H functionalization, alkene functionalization, carboxylation and cross-electrophile couplings are discussed, along with their related mechanistic aspects.

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“…Therefore, it is not surprising that electrochemistry has become extremely relevant. The recently emerged organic electrosynthesis is being adopted in both academia and industry as the twenty-first century's synthetic technique [48][49][50][51][52][53][54][55][56][57][58][59].…”

Section: Introductionmentioning

confidence: 99%

Electrosynthesis of 3,3′,5,5’-Tetramethyl-2,2′-biphenol in Flow

et al. 2020

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Abstract3,3′,5,5’-Tetramethyl-2,2′-biphenol is well known as an outstanding building block for ligands in transition-metal catalysis and is therefore of particular industrial interest. The electro-organic method is a powerful, sustainable, and efficient alternative to conventional synthetic approaches to obtain symmetric and non-symmetric biphenols. Here, we report the successive scale-up of the dehydrogenative anodic homocoupling of 2,4-dimethylphenol (4) from laboratory scale to the technically relevant scale in highly modular narrow gap flow electrolysis cells. The electrosynthesis was optimized in a manner that allows it to be easily adopted to different scales such as laboratory, semitechnical and technical scale. This includes not only the synthesis itself and its optimization but also a work-up strategy of the desired biphenols for larger scale. Furthermore, the challenges such as side reactions, heat development and gas evolution that arose during optimization are also discussed in detail. We have succeeded in obtaining yields of up to 62% of the desired biphenol.

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Organic Electrosynthesis: Applications in Complex Molecule Synthesis

Cited by 160 publications

References 298 publications

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

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

Recent Advances in Asymmetric Catalytic Electrosynthesis

Electrosynthesis of 3,3′,5,5’-Tetramethyl-2,2′-biphenol in Flow

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