Electrochemical oxidation of 3-substituted indoles

Sperry, Jonathan; Lindsay, Ashley C.; Giraldo, Jesús; Seo, Rumi; Kilmartin, Paul A.

doi:10.1039/d3ob00831b

Cited by 4 publications

References 49 publications

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Combining the Nonnatural Activity of Lipase and Electrocatalysis in One Pot: Sustainable and Regioselective Synthesis of C‐3 Alkylated Oxindoles

Singh,

Tyagi

2024

ChemCatChem

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Herein, we report an environment‐friendly protocol by integrating the non‐natural catalytic activity of lipase with electrocatalysis for synthesizing C‐3 alkylated oxindoles, which are part of many natural products and pharmaceuticals. Greatfyingly, Candida antarctica lipase B (CALB) is found to be highly active and regioselective for catalyzing the non‐natural C‐3 alkylation reaction at indole when combined with an electrochemical C‐2 oxidation process in the same vessels. Further, the generality and feasibility of the developed protocol are shown by employing several functional groups on the indole moiety and obtaining the desired products in moderate to good yield. Besides, the control experiments are set up along with the molecular docking studies to substantiate the role of the active site of Candida antarctica lipase B (CALB) in carrying out the regioselective C‐3 alkylation reaction. In addition, control experiments and cyclic voltammetry are performed to get insight into the electrochemical C‐2 oxidation process, and as a result, a plausible mechanism for the integrated process is presented.

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Combining the Nonnatural Activity of Lipase and Electrocatalysis in One Pot: Sustainable and Regioselective Synthesis of C‐3 Alkylated Oxindoles

Singh,

Tyagi

2024

ChemCatChem

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Hypervalent Iodine‐Mediated C3‐Trifluoropropionyloxylation of N‐Substituted Indoles

Tian,

Zhou,

Wang

et al. 2024

ChemistrySelect

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A metal‐free hypervalent iodine‐mediated C3‐trifluoropropionyloxylation of N‐substituted indoles was developed. (Bis‐trifluoropropanoate)iodobenzene was used as both the oxidant and fluorine source. The reaction was sensitive to the N‐protecting groups of the indoles. N‐acylated indoles provided 3‐trifluoropropionyloxylated indoles, while 3‐trifluoropropionyloxylated oxindoles were generated from indoles bearing N‐alkyl groups.

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Five-membered ring systems: Pyrroles and benzo analogs

Shan,

Lopchuk

2024

Progress in Heterocyclic Chemistry

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Electrochemical oxidation of 3-substituted indoles

Abstract: 2-Oxindoles are an abundant heteroaromatic motif in natural products and pharmaceuticals. An appealing method for accessing 2-oxindoles is by oxidation of the corresponding indole, a transformation currently executed using stoichiometric...

Cited by 4 publications

References 49 publications

Combining the Nonnatural Activity of Lipase and Electrocatalysis in One Pot: Sustainable and Regioselective Synthesis of C‐3 Alkylated Oxindoles

Combining the Nonnatural Activity of Lipase and Electrocatalysis in One Pot: Sustainable and Regioselective Synthesis of C‐3 Alkylated Oxindoles

Hypervalent Iodine‐Mediated C3‐Trifluoropropionyloxylation of N‐Substituted Indoles

Five-membered ring systems: Pyrroles and benzo analogs

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