Eosin Y photoredox catalyzed net redox neutral reaction for regiospecific annulation to 3-sulfonylindoles via anion oxidation of sodium sulfinate salts

TitleEosin Y photoredox catalyzed net redox neutral reaction for regiospecific annulation to 3-sulfonylindoles via anion oxidation of sodium sulfinate salts
Publication TypeJournal Article
Year of Publication2018
AuthorsRohokale, RS, Tambe, SD, Kshirsagar, UA
JournalOrganic & Biomolecular Chemistry
Volume16
Issue4
Pagination536-540
Date PublishedJAN
Type of ArticleArticle
ISSN1477-0520
Abstract

An eosin Y photoredox catalyzed net redox neutral process for 3-sulfonylindoles via the anionic oxidation of sodium sulfinate salts and its radical cascade cyclization with 2-alkynyl-azidoarenes was developed with visible light as a mediator. The reaction offers metal and oxidant/reductant free, visible light mediated vicinal sulfonamination of alkynes to 2-aryl/alkyl-3-sulfonylindoles and proceeds via the generation of a sulfur-centered radical through direct oxidation of the sulfinate anion by an excited photocatalyst with a reductive quenching cycle. The mild conditions, use of an organic dye as photo-catalyst, bench stability and easily accessible starting materials make the present approach green and attractive.

DOI10.1039/c7ob02977b
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)3.564
Divison category: 
Organic Chemistry

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