Communication
ChemComm
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Next, ligand 6 was applied to copper-catalyzed conjugate addi-
tion of diethylzinc to chalcone.16 The desired product 7 was
obtained with 26% ee. Although the enantioselectivity was low,
it indicates that the eight-membered skeleton has application
potential in asymmetric catalysis.
In conclusion, we have developed a facile method for the
synthesis of eight-membered nitrogen heterocycles through
Pd-catalyzed cross-coupling of 2-iodobiphenyls with 2-bromo-
benzylamines. C,C-Palladacycles that are formed via the C–H activa-
tion of 2-iodobiphenyls should act as the intermediates.
This reaction provides a new strategy for the construction of
medium-sized rings. The coupling reaction proceeded with high
diastereoselectivity to form enantiopure products. The resulting
eight-membered nitrogen heterocycles represent a novel type of
chiral scaffold, which has great potential to be applied in
asymmetric synthesis. Studies towards the synthesis of other
medium-sized rings and applications of the chiral products are
underway in our lab.
´
The authors acknowledge financial support from the National
Natural Science Foundation of China (No. 21672162 and 21971196).
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Conflicts of interest
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This journal is The Royal Society of Chemistry 2021