Promotion of S-nitrosation of cysteine by a {Co(NO)2}10 complex

Chiang, Chien‐Wei; Zhang, Kai-Wen; Chen, Jeng-Lung; Hsu, Liang-Ching; Huang, Wei-Hsiang; Chen, Hung-Chi; Lin, T.P.; Sun, C. P.; Yu-ning, Li

doi:10.1039/d3cc02784h

Chem. Commun.

2023

DOI: 10.1039/d3cc02784h

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Promotion of S-nitrosation of cysteine by a {Co(NO)₂}¹⁰ complex

Chien‐Wei Chiang

Kai-Wen Zhang

Jeng-Lung Chen

et al.

Abstract: S-nitrosothiols (SNOs) serve as endogenous carriers and donors of NO within living cells, releasing nitrosonium ion (NO+), NO, or other nitroso derivatives. In this study, we present a bioinspired {Co(NO)2}10...

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Electrochemical/Cobalt Dual Catalysis for Regioselective Tetramerization of Indoles

Liu,

Hung,

Jhang

et al. 2024

Asian J Org Chem

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Indoles are critically important heterocyclic building blocks with broad applications in pharmaceuticals, fragrances, agrochemicals, pigments, and materials. Recent advancements have highlighted bis‐indole derivatives and oligomerized indoles as promising scaffolds for anticancer compounds and materials in organic semiconductors. Despite the challenges in forming C–C bonds in indoles, we developed a novel method combining electrochemical and cobalt complex dual catalysis to achieve regioselective C3‐C3/C2‐C3 coupling. Using 1‐methylindole as a model substrate, we optimized reaction conditions to achieve a 90% yield of the tetramerized product. The method proved effective for various substituted indoles, with satisfactory yields for 6‐position substituents and poorer results for 5‐position due to steric hindrance, as confirmed by DFT calculations. The proposed mechanism involves initial C3‐C3 coupling facilitated by cobalt catalysis, followed by C2‐C3 coupling under electrochemical conditions, providing an efficient and environmentally benign strategy for synthesizing complex indole derivatives.

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Electrochemical/Cobalt Dual Catalysis for Regioselective Tetramerization of Indoles

Liu,

Hung,

Jhang

et al. 2024

Asian J Org Chem

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show abstract

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Promotion of S-nitrosation of cysteine by a {Co(NO)₂}¹⁰ complex

Abstract: S-nitrosothiols (SNOs) serve as endogenous carriers and donors of NO within living cells, releasing nitrosonium ion (NO+), NO, or other nitroso derivatives. In this study, we present a bioinspired {Co(NO)2}10...

Cited by 1 publication

References 20 publications

Electrochemical/Cobalt Dual Catalysis for Regioselective Tetramerization of Indoles

Electrochemical/Cobalt Dual Catalysis for Regioselective Tetramerization of Indoles

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