Categories: C-N Bond Formation > Synthesis of substituted N-heterocycles >
N-arylation
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Recent Literature
A mild, new aryl/heteroaryl C-N bond cross-coupling reaction via the
arylboronic acid/cupric acetate arylation of N-H containing heteroarenes
proceeds at room temperature exposed to air, and works for many heteroarenes
and arylboronic acids providing good yields of N-arylated heteroarenes.
P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T.
Chan, A. Combs, Tetrahedron Lett.,
1998, 39, 2941-2944.
4,7-Dimethoxy-1,10-phenanthroline is an efficient ligand for the mild,
copper-catalyzed N-arylation of imidazole with aryl iodides and
bromides. Various hindered and functionalized imidazoles and aryl halides
were transformed in good to excellent yields.
R. A. Altman, S. L. Buchwald, Org. Lett.,
2006,
8, 2779-2782.
N-Arylation of imidazoles and amines with arylboronic acids catalyzed
by copper-exchanged fluorapatite (CuFAP) in methanol at room temperature
gave N-arylimidazoles and N-arylamines in good yields. The use
of various arylboronic acids demonstrated the versatility of the reaction.
M. L. Kantam, G. T. Venkanna, C. Sridhar, B. Sreedhar, B. M. Choudary, J. Org. Chem., 2006,
71, 9522-9524.
N-arylation of either aryl iodides or aryl bromides with common
π-excessive nitrogen heterocycles (pyrroles, pyrazoles, indazoles,
imidazoles, and triazoles) was successfully performed in good yield with
catalysts derived from diamine ligands and CuI. General conditions were
found that tolerate various functional groups and hindered substrates.
J. C. Antilla, J. M. Baskin, T. E. Barder, S. L. Buchwald, J. Org. Chem.,
2004,
69, 5578-5587.
The use of N,N′-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene (SIPr)
as a ligand and tBuONa as the base for sequential palladium-catalyzed
intra- followed by intermolecular aryl amination enables the synthesis of
N-arylated five-, six- and seven-membered nitrogen heterocycles.
R. Omar-Amrani, R. Schneider, Y. Fort, Synthesis,
2004, 2257-2534.
Copper acetate promoted N-arylation of imides with boronic acids can be employed
as a major method for the synthesis of N3-aryl hydantoins.
H. M. Hügel, C. J. Rix, K. Fleck, Synlett, 2006,
2290-2292.
