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 a Burkhard KÖNIG

Základní údaje

Originální název

Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis

Autoři

MEYER, Andreas U. (276 Německo), Tomáš SLANINA (203 Česká republika, garant, domácí), Chang-Jiang YAO (156 Čína) a Burkhard KÖNIG (276 Německo)

Vydání

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

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 10.614

Kód RIV

RIV/00216224:14310/16:00089987

Organizační jednotka

Přírodovědecká fakulta

DOI

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

UT WoS

000367706800040

Klíčová slova anglicky

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

Štítky

AKR, rivok

Změněno: 27. 1. 2017 13:05, Mgr. Michaela Hylsová, Ph.D.

Anotace

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.

Návaznosti

LM2011028, projekt VaV

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

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, RECETOX Národní infrastruktura pro výzkum toxických látek v prostředí

LO1214, projekt VaV

Název: Centrum pro výzkum toxických látek v prostředí (Akronym: RECETOX)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Centrum pro výzkum toxických látek v prostředí

Citovat

MEYER, Andreas U., Tomáš SLANINA, Chang-Jiang YAO a Burkhard KÖNIG. Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis. ACS Catalysis. WASHINGTON: AMER CHEMICAL SOC, 2016, roč. 6, č. 1, s. 369-375. ISSN 2155-5435. Dostupné z: 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 a Burkhard KÖNIG. Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis. \textit{ACS Catalysis}. WASHINGTON: AMER CHEMICAL SOC, 2016, roč.~6, č.~1, s.~369-375. ISSN~2155-5435. Dostupné z: https://dx.doi.org/10.1021/acscatal.5b02410.

Podrobný výpis o publikaci