Synthesized similar structures to (13)- "4'-bromo-2',3,5,6'-tetramethoxy-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate" and also other subtitude functional group on 2',3,5,6' position- using the same procedures as are written in the paper in Supporting Information. The yields are reproducible.
However, when I am trying to do the next round of Negishi coupling using same procedue to make "4-bromo-2,3',3'',5',5'',6-hexamethoxy-4''-(methoxymethoxy)-1,1':4',1''-terphenyl" by coupling "5-bromo-1,3-dimethoxy-2-(methoxymethoxy)benzene" and "4'-bromo-2',3,5,6'-tetramethoxy-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate", the reaction did not happened.
By using "4-bromo-2,3',5',6-tetramethoxy-4'-(methoxymethoxy)-1,1'-biphenyl" and "4-bromo-2,6-dimethoxyphenyl trifluoromethanesulfonate" as reactant, the react yieald is reproducible again using same procedue.
Basicly, the Pd(0) catalyst did not react with 4'-bromo-2',3,5,6'-tetramethoxy-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate. So when we cite this procedue to do our own reaction, we have to think about our reactants properties at the first place.