Metal-Free Perfluoroarylation by Visible Light Photoredox
Catalysis

J 2016

Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis

MEYER, Andreas U., Tomáš SLANINA, Chang-Jiang YAO and Burkhard KÖNIG

Basic information

Original name

Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis

Authors

MEYER, Andreas U. (276 Germany), Tomáš SLANINA (203 Czech Republic, guarantor, belonging to the institution), Chang-Jiang YAO (156 China) and Burkhard KÖNIG (276 Germany)

Edition

ACS Catalysis, WASHINGTON, AMER CHEMICAL SOC, 2016, 2155-5435

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 10.614

RIV identification code

RIV/00216224:14310/16:00089987

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1021/acscatal.5b02410

UT WoS

000367706800040

Keywords in English

perfluorophenyl; photocatalysis; visible light; metal-free conditions; C-H arylation; transient spectroscopy

Abstract

V originále

Visible light and eosin Y catalyze the direct arylation of simple arenes with fluorinated aryl bromides by a photoredox process. The reaction scope is broad in fluorinated compounds and arenes and the general and simple procedure provides a metal-free alternative for the synthesis of synthetically valuable polyfluorinated biaryl structures. The mild reaction conditions allow a selective reaction with the alkaloid brucine without protection of functional groups illustrating the potential of the process for late stage functionalization. Mechanistic investigations reveal the photoreduction of eosin Y via its triplet state by triethylamine and subsequent electron transfer from the eosin Y radical anion to the polyfluorinated bromoarene, which fragments into the polyfluorinated aryl radical and a bromide anion. A radical chain reaction mechanism was excluded by a quenching factor analysis.

Links

LM2011028, research and development project

Name: RECETOX ? Národní infrastruktura pro výzkum toxických látek v prostředí

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 U., Tomáš SLANINA, Chang-Jiang YAO and Burkhard KÖNIG. Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis. ACS Catalysis. WASHINGTON: AMER CHEMICAL SOC, 2016, vol. 6, No 1, p. 369-375. ISSN 2155-5435. Available from: https://dx.doi.org/10.1021/acscatal.5b02410.

@article{1345777,
   author = {Meyer, Andreas U. and Slanina, Tomáš and Yao, ChangandJiang and König, Burkhard},
   article_location = {WASHINGTON},
   article_number = {1},
   doi = {http://dx.doi.org/10.1021/acscatal.5b02410},
   keywords = {perfluorophenyl; photocatalysis; visible light; metal-free conditions; C-H arylation; transient spectroscopy},
   language = {eng},
   issn = {2155-5435},
   journal = {ACS Catalysis},
   title = {Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis},
   url = {http://pubs.acs.org/doi/abs/10.1021/acscatal.5b02410},
   volume = {6},
   year = {2016}
}

TY  - JOUR
ID  - 1345777
AU  - Meyer, Andreas U. - Slanina, Tomáš - Yao, Chang-Jiang - König, Burkhard
PY  - 2016
TI  - Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis
JF  - ACS Catalysis
VL  - 6
IS  - 1
SP  - 369-375
EP  - 369-375
PB  - AMER CHEMICAL SOC
SN  - 21555435
KW  - perfluorophenyl
KW  - photocatalysis
KW  - visible light
KW  - metal-free conditions
KW  - C-H arylation
KW  - transient spectroscopy
UR  - http://pubs.acs.org/doi/abs/10.1021/acscatal.5b02410
L2  - http://pubs.acs.org/doi/abs/10.1021/acscatal.5b02410
N2  - Visible light and eosin Y catalyze the direct arylation of simple arenes with fluorinated aryl bromides by a photoredox process. The reaction scope is broad in fluorinated compounds and arenes and the general and simple procedure provides a metal-free alternative for the synthesis of synthetically valuable polyfluorinated biaryl structures. The mild reaction conditions allow a selective reaction with the alkaloid brucine without protection of functional groups illustrating the potential of the process for late stage functionalization. Mechanistic investigations reveal the photoreduction of eosin Y via its triplet state by triethylamine and subsequent electron transfer from the eosin Y radical anion to the polyfluorinated bromoarene, which fragments into the polyfluorinated aryl radical and a bromide anion. A radical chain reaction mechanism was excluded by a quenching factor analysis.
ER  -

MEYER, Andreas U., Tomáš SLANINA, Chang-Jiang YAO and Burkhard KÖNIG. Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis. \textit{ACS Catalysis}. WASHINGTON: AMER CHEMICAL SOC, 2016, vol.~6, No~1, p.~369-375. ISSN~2155-5435. Available from: https://dx.doi.org/10.1021/acscatal.5b02410.

Detailed Information on Publication Record