Categories: C-N Bond Formation > Synthesis of substituted N-heterocycles >
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.