TY  - JOUR
A1  - Schmidt, Bernd
A1  - Elizarov, Nelli
A1  - Berger, René
A1  - Petersen, Monib H.
T1  - From paracetamol to rolipram and derivatives - application of deacetylation-diazotation sequences and palladium-catalyzed matsuda-heck reaction
JF  - Synthesis
N2  - A six-step synthesis of the antidepressant rolipram from the popular analgetic 4-acetamidophenol (paracetamol) is described. The steps include oxidative functionalization of the aromatic core, diazonium salt formation via deacetylation-diazotation, Matsuda-Heck reaction, conjugate addition of nitromethane, and hydrogenative cyclization.
KW  - acetanilides
KW  - deacetylation
KW  - diazonium salts
KW  - palladium
KW  - Matsuda-Heck reaction
Y1  - 2013
U6  - https://doi.org/10.1055/s-0032-1316874
SN  - 0039-7881
VL  - 45
IS  - 9
SP  - 1174
EP  - 1180
PB  - Thieme
CY  - Stuttgart
ER  - 
TY  - JOUR
A1  - Schmidt, Bernd
A1  - Berger, René
T1  - A deacetylation-diazotation-coupling sequence - palladium-catalyzed CC bond formation with acetanilides as formal leaving groups
JF  - Advanced synthesis & catalysis
N2  - Acetanilides can be deacetylated and diazotized in situ, and subsequently used in Pd-catalyzed coupling reactions without isolation of the diazonium intermediate. Heck reactions, Suzuki cross-coupling reactions, and a Pd-catalyzed [2+2+1]cycloaddition have been investigated as terminating CC bond-forming steps of this one-flask sequence. The sequence does not require the exchange of solvents or removal of by-products between the individual steps, but proceeds by addition of reagents and catalysts in due course.
KW  - diazo compounds
KW  - Heck reaction
KW  - homogeneous catalysis
KW  - palladium
KW  - Suzuki coupling
Y1  - 2013
U6  - https://doi.org/10.1002/adsc.201200929
SN  - 1615-4150
VL  - 355
IS  - 2-3
SP  - 463
EP  - 476
PB  - Wiley-VCH
CY  - Weinheim
ER  -