TY  - JOUR
A1  - Schmidt, Bernd
A1  - Elizarov, Nelli
A1  - Riemer, Nastja
A1  - Hölter, Frank
T1  - Acetamidoarenediazonium Salts: Opportunities for Multiple Arene Functionalization
JF  - European journal of organic chemistry
N2  - Unlike their ortho counterparts, meta- and para-acetamidoanilines can be converted into the corresponding acetamidoarenediazonium salts. These offer various opportunities for multiple Pd-catalyzed arene functionalization reactions, such as Matsuda-Heck-, Suzuki-Miyaura- or Fujiwara-Moritani couplings.
KW  - Arenes
KW  - Amides
KW  - C-C coupling
KW  - Cross-coupling
KW  - Palladium
Y1  - 2015
U6  - https://doi.org/10.1002/ejoc.201500795
SN  - 1434-193X
SN  - 1099-0690
IS  - 26
SP  - 5826
EP  - 5841
PB  - Wiley-VCH
CY  - Weinheim
ER  - 
TY  - JOUR
A1  - Schmidt, Bernd
A1  - Riemer, Martin
A1  - Schilde, Uwe
T1  - Tandem Claisen Rearrangement/6-endo Cyclization Approach to Allylated and Prenylated Chromones
JF  - European journal of organic chemistry
N2  - Allyl, dimethylallyl and prenyl ethers derived from o-acyl-phenols reacted upon microwave irradiation to form C-allylated or -prenylated chromone derivatives, depending on the substitution pattern of the arene and the allyl substituent. The reaction proceeds through a tandem Claisen rearrangement and 6-endo-trig or 6-endo-dig cyclization sequence. For prenyl ethers, the tandem sequence can be extended by a Cope rearrangement to furnish 6-prenylchromones. The method is potentially useful for the synthesis of natural products and drugs.
KW  - Allylic compounds
KW  - Arenes
KW  - Oxygen heterocycles
KW  - Microwave chemistry
KW  - Rearrangement
KW  - Michael addition
Y1  - 2015
U6  - https://doi.org/10.1002/ejoc.201501151
SN  - 1434-193X
SN  - 1099-0690
IS  - 34
SP  - 7602
EP  - 7611
PB  - Wiley-VCH
CY  - Weinheim
ER  - 
TY  - JOUR
A1  - Schmidt, Bernd
A1  - Schultze, Christiane
T1  - A one-pot synthesis of pyranocoumarins through microwave-promoted propargyl claisen rearrangement/wittig olefination
JF  - European journal of organic chemistry
N2  - The reaction between propargyl ethers of hydroxybenzaldehydes and the ylide ethyl (triphenylphosphoranylidene)acetate was carried out under microwave irradiation to regioselectively afford angular pyranocoumarins. The chromene and coumarin heterocyclic scaffolds were simultaneously formed in the same synthetic step without changing the reaction conditions. The natural products seselin, braylin, and dipetalolactone were among the products synthesized by this method.
KW  - Domino reactions
KW  - Alkynes
KW  - Arenes
KW  - Oxygen heterocycles
KW  - Microwave chemistry
KW  - Rearrangement
Y1  - 2017
SN  - 1434-193X
SN  - 1099-0690
VL  - 2018
IS  - 2
SP  - 223
EP  - 227
PB  - Wiley-VCH Verl.
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  -