Categories: C-N Bond Formation > Synthesis of substituted N-heterocycles >
N-benzylation
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A simple Cu(I)-catalyzed C-N coupling of aliphatic halides with amines and
amides takes place readily at room temperature. The method uses CuBr, a common
and inexpensive atom transfer radical polymerization precatalyst, along with the
cheap ligand N,N,N',N'',N''-pentamethyldiethylenetriamine.
A. K. K. Fung, L.-J. Yu, M. S. Sherburn, M. L. Coote, J. Org. Chem., 2021, 86,
9723-3732.
A consecutive detosylation/alkylation transformation of tosylated indoles and
phenols with alkoxides/alcohols as the alkylation reagents features mild reaction conditions, high
ipso-selectivity, and good
functional group tolerance. A one-pot selective N-alkylation of
unprotected indoles with alcohols and TsCl is also realized.
M.-H. Zhu, C.-L. Yu, Y.-L. Feng, M. Usman, D. Zhong, X. Wang, N. Nesnas, W.-B.
Liu,
Org. Lett., 2019, 21, 7073-7077.