TY  - JOUR
A1  - Schmidt, Bernd
A1  - Riemer, Martin
T1  - Suzuki-Miyaura coupling of halophenols and phenol boronic acids: systematic investigation of positional isomer effects and conclusions for the synthesis of phytoalexins from Pyrinae
T2  - The journal of organic chemistry
N2  - The Suzuki-Miyaura couplings of o-, m-, and p-halophenols with o-, m-, and p-phenol boronic acids were investigated for all combinations under standardized conditions, using Pd/C as a heterogeneous catalyst and water as a solvent. In the case of iodophenols, conventional heating was used, while for bromophenols significantly better results could be obtained using microwave irradiation. This systematic study revealed that 2,4'-biphenol is particularly difficult to access, irrespective of the starting materials used, but that these difficulties can be overcome by using different additives. The conclusions drawn from this investigation allowed us to identify conditions for the protecting group-free or minimized total synthesis of biaryl-type phytoalexins. These compounds possess antibacterial activity and are produced by fruit trees as a response to microbial infection.
Y1  - 2014
UR  - https://publishup.uni-potsdam.de/frontdoor/index/index/docId/37859
SN  - 0022-3263
VL  - 79
IS  - 9
SP  - 4104
EP  - 4118
PB  - American Chemical Society
CY  - Washington
ER  -