Categories: C-N Bond Formation >
Synthesis of carbamates
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Recent Literature
The arylation of N-H and O-H containing compounds at room temperature with
phenylboronic acids is promoted in the presence of cupric acetate and a tertiary
amine. Substrates include phenols, amines, anilines, amides, imides, ureas,
carbamates, and sulfonamides.
D. M. T. Chan, K. L. Monaco, R.-P. Wang, M. P. Winteres, Tetrahedron Lett.,
1998, 39, 2933-2936.
Catalysts generated from Pd2(dba)3 and biphenyl ligands efficiently
promote the coupling of amides and carbamates with unactivated vinyl triflates
and tosylates, to provide enamides in good to excellent yields.
M. C. Willis, G. N. Brace, I. P. Holmes,
Synthesis, 2005, 3229-3234.
The AuCl3-PPh3-catalyzed direct
three-component Mannich reactions of aryl aldehydes, aryl ketones, and
carbamates led to N-protected β-aryl-β-amino ketones.
L.-W. Xu, C.-G. Xia, L. Li, J. Org. Chem.,
2004,
69, 8482-8484.
A versatile and efficient
copper-catalyzed amidation of vinyl bromides and iodides has been developed.
The protocol, which uses a combination of copper iodide and N,N'-dimethyl
ethylenediamine, tolerates substrates bearing ester, silyl ether, and amino
groups.
L. Jiang, G. E. Job, A. Klapars, S. L. Buchwald, Org.
Lett., 2003, 5, 3667-3669.
A mild, ruthenium-catalyzed anti-Markovnikov addition of secondary amides,
anilides, lactames, ureas, bislactames, and carbamates to terminal alkynes
has been developped. Two complementary protocols provide either the E
or the Z isomers.
L. J. Goossen, J. E. Rauhaus, G. Deng, Angew. Chem. Int. Ed., 2005,
44, 4042-4045.
A range of enol triflates can be coupled with amides, carbamates, and
sulfonamides using palladium catalysis. This method allows the synthesis of
enamides, which may not be readily available by other means.
D. J. Wallace, D. J. Klauber, C.-Y. Chen, R. P.
Volante, Org. Lett., 2003, 5, 4749-4752.
CeCl3 • 7H2O/NaI supported on
neutral alumina (Al2O3) promotes heteroatom Michael
additions under solvent-free conditions. The CeCl3 • 7H2O/NaI/Al2O3
system works well for hetero-Michael additions of weak nucleophiles such as
imidazoles and carbamates to various acceptors.
G. Bartoli, M. Bartolacci, A. Giuliani, E. Marcantoni, M. Massaccesi, E.
Torregiani, J. Org. Chem., 2005,
70, 169-174.
An efficient palladium-catalyzed asymmetric amination of 2,3-allenyl
phosphates with nitrogen nucleophiles such as amines, hydroxylamines, and
imides can be performed in presence of SEGPHOS or MeOBIPHEP ligand,
affording the corresponding optically active 1-aminated derivatives with
high enantiomeric excess.
Y. Imada, M. Nishida, K. Kutsuwa, S.-I. Murahashi, T. Naota, Org. Lett.,
2005,
7, 5837-5839.
