Synthesis of carbamates

Related

Name Reactions

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 direct reaction between carbamates and achiral allylic carbonates to form branched, conveniently protected primary allylic amines with high regioselectivity and enantioselectivity occurs without base in the presence of a metalacyclic iridium catalyst containing a labile ethylene ligand.
D. J. Weix, D. Marković, M. Ueda, J. F. Hartwig, Org. Lett., 2009, 11, 2944-2947.

Iridium-catalyzed allylation of potassium trifluoroacetamide or the highly reactive ammonia equivalent lithium di-tert-butyliminodicarboxylate forms a range of conveniently protected, primary, α-branched allylic amines in high yields, high branched-to-linear regioselectivities, and high enantiomeric excess.
M. J. Pouy, A. Leitner, D. J. Weix, S. Ueno, J. F. Hartwig, Org. Lett., 2007, 9, 3949-3952.

Alkylcarboxamides can be converted to the respective alkylcarbamates by Hofmann rearrangement using hypervalent iodine species generated in situ from PhI and Oxone in methanol. In addition, substituted benzamides can be converted to the respective quinone derivatives by treatment with Oxone and iodobenzene in aqueous acetonitrile.
A. A. Zagulyaeva, C. T. Banek, M. S. Yusubov, V. V. Zhdankin, Org. Lett., 2010, 12, 4644-4647.

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.

A facile route to ynamides in high yields was achieved through an iron-catalyzed C-N coupling reaction of amides with alkynyl bromides in the presence of 20 mol % of N,N′-dimethylethane-1,2-diamine (DMEDA).
B. Yao, Z. Liang, T. Niu, Y. Zhang, J. Org. Chem., 2009, 74, 4630-4633.

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.