Categories: C-N Bond Formation > Synthesis of substituted N-heterocycles >
N-arylation
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N-Arylation of azoles and amines with arylboronic acids was efficiently
carried out with heterogeneous copper(I) oxide in methanol at room temperature
under base-free conditions. Various arylboronic acids and amines were converted
to the corresponding N-arylazoles and N-arylamines in very good
yields, demonstrating the versatility of the reaction.
B. Sreedhar, G. T. Venkanna, K. B. S. Kumar, V. Balasubrahmanyam, Synthesis, 2008,
795-799.
An efficient copper(I) bromide catalyzed N-arylation of azoles with a
variety of aromatic bromides and iodides under mild conditions displayed great
functional group compatibility and excellent reactive selectivity.
H. Chen, D. Wang, X. Wang, W. Huang, Q. Cai, K. Ding, Synthesis, 2010,
1505-1511.
A copper-catalyzed N-arylation reaction of imidazole proceeds under very
mild conditions in the absence of additional ligand. This protocol tolerates an
array of thermally sensitive functional groups, but also achieves high
chemoselectivity.
L. Zhu, G. Li, L. Luo, P. Guo, J. Lan, J. You, J. Org. Chem., 2009,
74, 2200-2202.
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.
CuI-catalyzed coupling reactions of tetrabutylammonium pyridin-2-olates with
aryl iodides allow an efficient synthesis of N-aryl pyridine-2-ones. This
coupling reaction is mild, high-yielding, remarkably chemoselective (N- vs.
O-arylation), and tolerates labile functional groups.
H. Zhang, B.-C. Chen, B. Wang, S. T. Chao, R. Zhao, N. Lim, B. Balasubramanian, Synthesis, 2008,
1523-1524.
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.
