Categories: C-N Bond Formation > Amines >
Synthesis of arylamines
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A Chan-Lam coupling using methylboronic acid enables a selective monomethylation
of anilines. An incubation period of the substrate with the copper reagent is
needed before addition of the methylboronic acid. N-Methylanilines are
synthesized in good yields.
I. González, J. Mosquera, C. Guerrero, R. Rodríguez, Jacobo Cruces, Org. Lett., 2009,
11, 1677-1680.
A simple copper-promoted N-monoalkylation of anilines that utilizes alkyl
boronic acids as the alkylating partner is carried out in refluxing dioxane and
allows a number of structurally and electronically diverse anilines to be
functionalized in a single step. A broad study was carried out to demonstrate
the utility of this new methodology for the preparation of phenethylanilines.
M. Larrosa, C. Guerrero, R. Rodríguez, J. Cruces, Synlett, 2010,
2101-2105.
In the presence of N,N,N′,N′-tetramethylethylenediamine (TMEDA) as an
additive, easily prepared and handled N-chloroamines react with aryl
Grignard reagents to give various arylamines in good to excellent yields.
Functional groups such as ester and nitrile are tolerated.
T. Hatakeyama, Y. Yoshimoto, S. K. Ghorai, M. Nakamura, Org. Lett., 2010,
12, 1516-1519.
A rhodium-catalyzed amination reaction of aryl halides with amines takes place
in the presence of a N-heterocyclic carbene ligand. The active metal
species responsible for the reaction progress was identified. This convenient
and mild procedure for Rh-catalyzed N-arylation displays a wide range of
substrate scope and high degree of functional group tolerance.
M. Kim, S. Chang, Org. Lett., 2010,
12, 1640-1643.
The sequential combination of Ti-catalyzed hydroamination of alkynes followed
by the Ti-catalyzed hydrosilylation of the intermediate imines is an efficient
one-pot process for the conversion of alkynes and primary amines into secondary
amines.
A. Heutling, F. Pohlki, I. Bytschkov, S. Doye, Angew. Chem. Int. Ed., 2005,
44, 2951-2954.
1,2,3-triazole-bound cationic Au(I) catalysts possess much better thermal
stability than literature-reported Au catalysts, including IPrAu•NTf2.
By application of these catalysts, challenging intermolecular hydroaminations
were achieved with less-reactive internal alkynes and unprotected aliphatic
amines, giving excellent yields with low catalyst loading.
H. Duan, S. Sengupta, J. L. Petersen, N. G. Akhmedov, X. Shi, J. Am. Chem. Soc., 2009,
131, 12100-12102.
An efficient intermolecular hydroamination of unactivated alkenes with anilines
catalyzed by lanthanide salts gives Markovnikov products in good yields.
P. Yin, T.-P. Loh, Org. Lett., 2009,
11, 3791-3793.
N-Alkylaminobenzenes
were prepared in a simple and efficient one-pot synthesis by reduction of
nitrobenzenes followed by reductive amination with decaborane (B10H14)
in the presence of 10% Pd/C.
J. W. Bae, Y. J. Cho,
S. H. Lee, C.-O. M. Yoon, C. M. Yoon, Chem. Commun., 2000,
1857-1858.
Cooperative catalysis of an Ir(III)-diamine complex and a chiral phosphoric
acid or its conjugate base enables a direct reductive amination of a wide range
of ketones.
C. Li, B. Villa-Marcos, J. Xiao, J. Am. Chem. Soc., 2009,
131, 6967-6969.
The NiCl2(PPh3)2-PPh3-catalyzed cross-coupling of bromomagnesium diarylamides, generated in situ from
diarylamines, with aryl bromides or iodides is an inexpensive, convenient, and practical method
for the synthesis of triarylamines.
C. Chen, L.-M. Yang, Org. Lett., 2005,
7, 2209-2211.
Air- and moisture-stable Ni(II)-(σ-aryl) complexes, associated with N-heterocyclic
carbene ligands, produce a catalytically active Ni(0) species in situ for an
efficient amination of aryl chlorides with anilines and secondary cyclic amines
under mild conditions.
C. Chen, L-M. Yang, J. Org. Chem., 2007,
72, 6324-6327.
A rhodium-catalyzed regioselective amination of secondary allylic
trichloroacetimidates with unactivated aromatic amines gives N-arylamines
in high yields and regioselectivity, favoring the branched amination products.
The presence of the trichloroacetimidate leaving group was found to be critical
for successful regioselective amination reactions with unactivated aromatic
amines.
J. S. Arnold, R. F. Stone, H. M. Nguyen, Org. Lett., 2010,
12, 4580-4583.
Various allyl carbonates have been converted under Fe catalysis into
essentially regio- and stereoisomerically pure allyl amines. Catalytic
amounts of piperidinium hydrochloride as a buffer retard catalyst
decomposition.
B. Plietker, Angew. Chem. Int. Ed., 2006,
45, 6053-6056.
p-Toluenesulfonic acid efficiently catalyzes direct
nucleophilic substitutions of the hydroxy groups of propargylic alcohols with a
large variety of carbon- and heteroatom-centered nucleophiles. Reactions can be
conducted under mild conditions and in air without the need for dried
solvents.
R. Sanz, A. Martinez, J. M. Alvarez-Gutierrez, F. Rodriquez, Eur. J. Org. Chem., 2006,
1383-1386.
An efficient and very simple conjugate addition of aromatic and aliphatic
amines to α,β-unsaturated carbonyl compounds under solvent-free conditions in
the presence of catalytic amount of silicon tetrachloride gave the corresponding
Michael adducts with very good yields.
N. Azizi, R. Baghi, H. Ghafuri, M. Boloutchian, M. Hashemi, Synlett, 2010,
379-382.
