TY  - JOUR
A1  - Schultze, Christiane
A1  - Foß, Stefan
A1  - Schmidt, Bernd
T1  - 8-Prenylflavanones through microwave promoted tandem claisen rearrangement/6-endo-trig cyclization and cross metathesis
JF  - European journal of organic chemistry
N2  - Prenylated flavanones were obtained from ortho-allyloxy chalcones through a one-pot sequence of Claisen rearrangement and 6-endo-trig cyclization, followed by olefin cross metathesis of the intermediate allyl flavanones with 2-methyl-2-butene. The synthetic utility of this route is illustrated for the synthesis of several naturally occurring prenyl flavanones.
KW  - tandem reactions
KW  - arenes
KW  - oxygen heterocycles
KW  - microwave chemistry
KW  - rearrangement
Y1  - 2020
U6  - https://doi.org/10.1002/ejoc.202001378
SN  - 1434-193X
SN  - 1099-0690
VL  - 2020
IS  - 47
SP  - 7373
EP  - 7384
PB  - Wiley-VCH
CY  - Weinheim
ER  - 
TY  - JOUR
A1  - Sand, Patrick
A1  - Schmidt, Bernd
T1  - Pd-catalyzed oxidative sulfoalkenylation of acetanilides and traceless removal of the catalyst directing group
JF  - ChemistrySelect
N2  - The palladium-catalyzed oxidative Heck-reaction, also referred to as Fujiwara-Moritani-reaction, has been investigated for the synthesis of styrenylsulfonyl compounds. Acetanilides and vinylsulfonyl compounds undergo dehydrogenative coupling reactions in moderate to quantitative yields, using benzoquinone as the oxidant of choice. Potassium peroxodisulfate, which had previously been identified as a superior oxidant for the coupling with acrylates, did not provide any coupling products with these olefins. Traceless removal of the catalyst directing group through a deacetylation-diazotation-coupling (DDC) sequence was demonstrated for 2-arylethene sulfones.
KW  - arenes
KW  - C− H activation
KW  - Heck reactions
KW  - Palladium
KW  - sulfones
Y1  - 2021
U6  - https://doi.org/10.1002/slct.202101009
SN  - 2365-6549
VL  - 6
IS  - 14
SP  - 3563
EP  - 3567
PB  - Wiley-VCH
CY  - Weinheim
ER  - 
TY  - JOUR
A1  - Holec, Jan
A1  - Rybáček, Jiří
A1  - Vacek, Jaroslav
A1  - Karras, Manfred
A1  - Bednárová, Lucie
A1  - Budesinsky, Milos
A1  - Slusna, Michaela
A1  - Holy, Petr
A1  - Schmidt, Bernd
A1  - Stará, Irena G.
A1  - Starý, Ivo
T1  - Chirality-Controlled Self-Assembly of Amphiphilic Dibenzo[6]helicenes into Langmuir-Blodgett Thin Films
JF  - Chemistry - a European journal
N2  - Racemic and highly enantioenriched 3-methoxycarbonyl, 3-carboxy, and 3-hydroxymethyl derivatives of dibenzo[6]helicene were prepared. The Langmuir layers of these helicenes were formed at the air-water interface and transferred onto solid substrates to afford Langmuir-Blodgett films, which were then studied by ambient atomic force microscopy and (chir)optical spectroscopy. Significant differences were found in the behaviour of the Langmuir layers as well as in the morphology, UV/Vis, electronic circular dichroism (ECD), and fluorescence spectra of the Langmuir-Blodgett thin films depending on the molecular chirality and nature of the polar group. The experimental results were supported by molecular dynamics simulations.
KW  - arenes
KW  - chirality
KW  - helical structures
KW  - Langmuir-Blodgett films
KW  - self-assembly
Y1  - 2019
U6  - https://doi.org/10.1002/chem.201901695
SN  - 0947-6539
SN  - 1521-3765
VL  - 25
IS  - 49
SP  - 11494
EP  - 11502
PB  - Wiley-VCH
CY  - Weinheim
ER  - 
TY  - JOUR
A1  - Bauch, Marcel
A1  - Böttcher, Dominique
A1  - Bornscheuer, Uwe T.
A1  - Linker, Torsten
T1  - Enzymatic Cleavage of Aryl Acetates
JF  - ChemCatChem : heterogeneous & homogeneous & bio- & nano-catalysis ; a journal of ChemPubSoc Europe
N2  - Seven enzymes have been screened for the cleavage of aryl acetates. Phenyl and naphthyl acetates react with lipases and esterases, whereas the sterically demanding anthracene acetate gave a conversion only with porcine liver esterase and esterase 2 from Bacillus subtilis (BS2). These two enzymes have been employed on a preparative (0.5 mmol) scale and afforded cleavage products in 91 and 94% yields, even for anthracene acetate. Thus, this method is superior to chemical cleavage with catalytic amounts of sodium methoxide (Zemplen conditions), which gave only low conversions. Finally, regioselectivity has been achieved with an anthracene bisacetate, in which an ethyl group controls the cleavage of the first acetate. This indicates that steric interactions play a crucial role in the enzymatic cleavage of aryl acetates, which might be interesting for future applications or the development of enzyme inhibitors.
KW  - arenes
KW  - enzyme catalysis
KW  - regioselectivity
KW  - steric hindrance
KW  - substituent effects
Y1  - 2016
U6  - https://doi.org/10.1002/cctc.201600678
SN  - 1867-3880
SN  - 1867-3899
VL  - 8
SP  - 2853
EP  - 2857
PB  - Wiley-VCH
CY  - Weinheim
ER  - 
TY  - JOUR
A1  - Klaper, Matthias
A1  - Linker, Torsten
T1  - Evidence for an oxygen anthracene sandwich complex
JF  - Angewandte Chemie : a journal of the Gesellschaft Deutscher Chemiker ; International edition
KW  - arenes
KW  - peroxides
KW  - sandwich complexes
KW  - singlet oxygen
KW  - interactions
Y1  - 2013
U6  - https://doi.org/10.1002/anie.201304768
SN  - 1433-7851
SN  - 1521-3773
VL  - 52
IS  - 45
SP  - 11896
EP  - 11899
PB  - Wiley-VCH
CY  - Weinheim
ER  -