Eosin Y (EY) Photoredox-Catalyzed Sulfonylation of Alkenes:
Scope and Mechanism

J 2016

Eosin Y (EY) Photoredox-Catalyzed Sulfonylation of Alkenes: Scope and Mechanism

MEYER, Andreas Uwe; Karolína STRAKOVÁ; Tomáš SLANINA and Burkhard KÖNIG

Basic information

Original name

Eosin Y (EY) Photoredox-Catalyzed Sulfonylation of Alkenes: Scope and Mechanism

Authors

MEYER, Andreas Uwe (276 Germany); Karolína STRAKOVÁ (203 Czech Republic); Tomáš SLANINA (203 Czech Republic, guarantor, belonging to the institution) and Burkhard KÖNIG (276 Germany)

Edition

Chemistry - A European Journal, WEINHEIM, Wiley, 2016, 0947-6539

Other information

Language

English

Type of outcome

Article in a journal

Field of Study

10401 Organic chemistry

Country of publisher

Germany

Confidentiality degree

is not subject to a state or trade secret

References:

URL

Impact factor

Impact factor: 5.317

RIV identification code

RIV/00216224:14310/16:00093214

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1002/chem.201601000

UT WoS

000380270100038

EID Scopus

2-s2.0-84966560516

Keywords in English

alkyl sulfinates; photocatalysis; reaction mechanisms; transient spectroscopy; vinyl sulfones

Abstract

V originále

Alkyl- and aryl vinyl sulfones were obtained by eosin Y (EY)-mediated visible-light photooxidation of sulfinate salts and the reaction of the resulting S-centered radicals with alkenes. Optimized reaction conditions, the sulfinate and alkene scope, and X-ray structural analyses of several reaction products are provided. A detailed spectroscopic study explains the reaction mechanism, which proceeds through the EY radical cation as key intermediate oxidizing the sulfinate salts.

Links

LM2015051, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX RI)

Investor: Ministry of Education, Youth and Sports of the CR

LO1214, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX)

Investor: Ministry of Education, Youth and Sports of the CR

Cite

MEYER, Andreas Uwe; Karolína STRAKOVÁ; Tomáš SLANINA and Burkhard KÖNIG. Eosin Y (EY) Photoredox-Catalyzed Sulfonylation of Alkenes: Scope and Mechanism. Chemistry - A European Journal. WEINHEIM: Wiley, 2016, vol. 22, No 25, p. 8694-8699. ISSN 0947-6539. Available from: https://dx.doi.org/10.1002/chem.201601000.

@article{1369951,
   author = {Meyer, Andreas Uwe and Straková, Karolína and Slanina, Tomáš and König, Burkhard},
   article_location = {WEINHEIM},
   article_number = {25},
   doi = {http://dx.doi.org/10.1002/chem.201601000},
   keywords = {alkyl sulfinates; photocatalysis; reaction mechanisms; transient spectroscopy; vinyl sulfones},
   language = {eng},
   issn = {0947-6539},
   journal = {Chemistry - A European Journal},
   title = {Eosin Y (EY) Photoredox-Catalyzed Sulfonylation of Alkenes: Scope and Mechanism},
   url = {http://onlinelibrary.wiley.com/doi/10.1002/chem.201601000/abstract?systemMessage=WOL+Usage+report+download+page+will+be+unavailable+on+Friday+27th+January+2017+at+23%3A00+GMT%2F+18%3A00+EST%2F+07%3A00+SGT+%28Saturday+28th+Jan+for+SGT%29++for+up+to+2+hour},
   volume = {22},
   year = {2016}
}

TY  - JOUR
ID  - 1369951
AU  - Meyer, Andreas Uwe - Straková, Karolína - Slanina, Tomáš - König, Burkhard
PY  - 2016
TI  - Eosin Y (EY) Photoredox-Catalyzed Sulfonylation of Alkenes: Scope and Mechanism
JF  - Chemistry - A European Journal
VL  - 22
IS  - 25
SP  - 8694-8699
EP  - 8694-8699
PB  - Wiley
SN  - 09476539
KW  - alkyl sulfinates
KW  - photocatalysis
KW  - reaction mechanisms
KW  - transient spectroscopy
KW  - vinyl sulfones
UR  - http://onlinelibrary.wiley.com/doi/10.1002/chem.201601000/abstract?systemMessage=WOL+Usage+report+download+page+will+be+unavailable+on+Friday+27th+January+2017+at+23%3A00+GMT%2F+18%3A00+EST%2F+07%3A00+SGT+%28Saturday+28th+Jan+for+SGT%29++for+up+to+2+hour
L2  - http://onlinelibrary.wiley.com/doi/10.1002/chem.201601000/abstract?systemMessage=WOL+Usage+report+download+page+will+be+unavailable+on+Friday+27th+January+2017+at+23%3A00+GMT%2F+18%3A00+EST%2F+07%3A00+SGT+%28Saturday+28th+Jan+for+SGT%29++for+up+to+2+hour
N2  - Alkyl- and aryl vinyl sulfones were obtained by eosin Y (EY)-mediated visible-light photooxidation of sulfinate salts and the reaction of the resulting S-centered radicals with alkenes. Optimized reaction conditions, the sulfinate and alkene scope, and X-ray structural analyses of several reaction products are provided. A detailed spectroscopic study explains the reaction mechanism, which proceeds through the EY radical cation as key intermediate oxidizing the sulfinate salts.
ER  -

MEYER, Andreas Uwe; Karolína STRAKOVÁ; Tomáš SLANINA and Burkhard KÖNIG. Eosin Y (EY) Photoredox-Catalyzed Sulfonylation of Alkenes: Scope and Mechanism. \textit{Chemistry - A European Journal}. WEINHEIM: Wiley, 2016, vol.~22, No~25, p.~8694-8699. ISSN~0947-6539. Available from: https://dx.doi.org/10.1002/chem.201601000.

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