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  - Sand, Patrick
A1  - Schmidt, Bernd
T1  - Ruthenium-catalyzed sulfoalkenylation of acetanilides and dual-use of the catalyst directing group
JF  - European journal of organic chemistry
N2  - In contrast to vinylsulfonates and vinylsulfones, vinylsulfonamides are unreactive in Pd-catalyzed oxidative Heck-coupling reactions with acetanilides. This limitation has been resolved by using a C-H-activation protocol based on Ru-Cu-Ag-catalysis. Overall, the Ru-Cu-Ag-catalyzed conditions turned out to be more reliable and showed better reproducibility than the Pd-catalyzed C-H-activation. The coupling products thus obtained are functionalized styrenyl sulfones and -sulfonamides which can be used as starting materials for the synthesis of sulfonyl pyrroles and sulfonyl pyrrolo[2,3-c]quinolines.
KW  - Arenes
KW  - C-H activation
KW  - Heterocycles
KW  - Ruthenium
KW  - Sulfonamides
Y1  - 2021
U6  - https://doi.org/10.1002/ejoc.202101216
SN  - 1434-193X
SN  - 1099-0690
VL  - 2021
IS  - 40
SP  - 5497
EP  - 5506
PB  - Wiley-VCH
CY  - Weinheim
ER  -