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

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

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

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

Citovat

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.

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   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.

Detailed Information on Publication Record