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

Rajendra S. Rohokale; Shrikant D. Tambe; Umesh A. Kshirsagar

doi:10.1039/c7ob02977b

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

Rajendra S. Rohokale, Shrikant D. Tambe, Umesh A. Kshirsagar

Research output: Contribution to journal › Article › peer-review

39 Scopus citations

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.

Original language	English
Pages (from-to)	536-540
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	16
Issue number	4
DOIs	https://doi.org/10.1039/c7ob02977b
State	Published - 1 Jan 2018
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Eosin y photoredox catalyzed net redox neutral reaction for regiospecific annulation to 3-sulfonylindoles: Via anion oxidation of sodium sulfinate salts",

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.",

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AU - Kshirsagar, Umesh A.

PY - 2018/1/1

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AB - 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.

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

Abstract

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