Controllable Synthesis of Mono‐ and Bis‐sulfenylindoles from Indoles and Various Sulfenylation Agents Using KI/SeO2 System

An efficient method for selective synthesis of mono‐ and bis‐sulfenylindoles was developed using a novel aerobic catalytic oxidation system KI/SeO2 for sulfenylation of indoles with disulfide/thiols. The selectivity was controlled by varying the amount of the catalytic system and sulfenylation agent...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-10, Vol.2022 (38), p.n/a
Main Authors: Benchawan, Thewika, Saeeng, Rungnapha
Format: Article
Language:English
Subjects:
C−H Functionalization
C−S Bond formation
Indoles
Nitrogen heterocycles
Oxidation
Selectivity
Selenium dioxide
Sulfenylation
Synthesis
Synthetic methods
Thiols
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Summary:An efficient method for selective synthesis of mono‐ and bis‐sulfenylindoles was developed using a novel aerobic catalytic oxidation system KI/SeO2 for sulfenylation of indoles with disulfide/thiols. The selectivity was controlled by varying the amount of the catalytic system and sulfenylation agents. The reaction features easy operation, mild reaction conditions, good atom economy, gram‐scalability, and a metal‐free approach furnishing desired products in up to excellent yields. An efficient method for selective and controllable sulfenylation of indoles to synthesize mono‐ and bis‐sulfenylindoles was reported by using a novel aerobic catalytic oxidation system KI/SeO2 for sulfenylation of indoles with disulfide/thiols. The method is scalable, not sensitive to moisture, and can proceed without metal catalyst.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202200752