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Investigating radical cation chain processes in the electrocatalytic Diels-Alder reaction.

ABSTRACT: Single electron transfer (SET)-triggered radical ion-based reactions have proven to be powerful options in synthetic organic chemistry. Although unique chain processes have been proposed in various photo- and electrochemical radical ion-based transformations, the turnover number, also referred to as catalytic efficiency, remains unclear in most cases. Herein, we disclose our investigations of radical cation chain processes in the electrocatalytic Diels-Alder reaction, leading to a scalable synthesis. A gram-scale synthesis was achieved with high current efficiency of up to 8000%. The reaction monitoring profiles showed sigmoidal curves with induction periods, suggesting the involvement of intermediate(s) in the rate determining step.

SUBMITTER: Imada Y

PROVIDER: S-EPMC5870144 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Investigating radical cation chain processes in the electrocatalytic Diels-Alder reaction.

Imada Yasushi Y Okada Yohei Y Chiba Kazuhiro K

Beilstein journal of organic chemistry 20180316

Single electron transfer (SET)-triggered radical ion-based reactions have proven to be powerful options in synthetic organic chemistry. Although unique chain processes have been proposed in various photo- and electrochemical radical ion-based transformations, the turnover number, also referred to as catalytic efficiency, remains unclear in most cases. Herein, we disclose our investigations of radical cation chain processes in the electrocatalytic Diels-Alder reaction, leading to a scalable synth ...[more]

PMID: 29623126

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