10.1002/anie.201902825
Angewandte Chemie International Edition
COMMUNICATION
the trend I > Br > Cl (Figure S22a).[22] In pH-dependent
experiments, the reaction is faster at higher pH (Figure S22b)
because the base facilitates the required deprotonation. We also
investigate the reaction using different types of bases (Figure
S21) and Ni catalysts with different sizes (Figure S22c). In
addition to the SERS monitoring, the synthetic C-H arylation is
performed using bromobenzene and benzene as the model
reactants. Table 1 lists the yields of biphenyl at different reaction
conditions. Compared with the standard yield of 68.9%, reaction
without adding benzene exhibits a reduced yield of 9.4%. At
70 °C in the dark, only trace amount of biphenyl is produced.
Wavelength-dependent results (Figure S25) indicate that
illumination at shorter wavelengths leads to higher yield, which is
consistent with the absorption spectrum of Ni NPs. These
experiments further confirm the reaction mechanism in Figure 4
and also give the appropriate conditions to perform synthetic C-
H arylation reactions.
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Acknowledgements
This work was supported by the National Natural Science
Foundation of China (21775074, 51601098 & 21861132016),
the Natural Science Foundation of Tianjin (17JCQNJC05400)
and the National Key R&D Program (2017YFA0206702 &
2016YFB0901502). We thank the reviewer for very fruitful
comments.
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Keywords: Surface-enhanced Raman spectroscopy • C-H
arylation • nanoparticles • self-assembly • photocatalysis
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