Categories: C-C Bond Formation > Amines, Arenes >
Synthesis of benzylamines
| Related: |
 |
 |
 |
Recent Literature
A Mannich-like zinc-mediated three-component reaction of aromatic halides,
amines, and paraformaldehyde allows the straightforward synthesis of a range of
functionalized tertiary benzylamines. This procedure involves the in situ
formation of arylzinc reagents.
E. Le Gall, A. Decompte, T. Martens, M. Troupel, Synthesis, 2010,
249-254.
Scope and limitations of the Suzuki-Miyaura reaction of N,N-dialkylaminomethyltrifluoroborates
with aryl halides were investigated. Aryl chlorides, iodides, and triflates
coupled in good to excellent yields to give N,N-dialkylbenzylic amines.
G. A. Molander, P. E. Gormisky, D. L. Sandrock, J. Org. Chem., 2008,
73, 2052-2057.
The synthesis of free α-chiral amines by a one-pot multicomponent procedure
involves the formation of N-diphenylphosphinoylimines from
commercially available starting materials and the subsequent
enantioselective addition of diakylzinc reagents using an air-stable
precatalyst complex.
A. Cote, A. B. Charette, J. Org. Chem.,
2005,
70, 10864-10867.
An asymmetric arylation of N-tosylimines with arylboronic acids was
realized by using a chiral cationic C2-symmetric N-heterocyclic
carbene Pd2+ diaquo complex as catalyst in combination with K3PO4
• 3 H2O in THF at 4°C in the presence of powdered 4 Å MS to afford
the corresponding adducts in excellent yields and good enantioselectivities.
G.-N. Ma, T. Zhang, M. Shi, Org. Lett., 2009,
11, 875-878.
A highly efficient three-component coupling reaction between thioformamides and
organolithium and Grignard reagents was developed. The generality of the process
has been demonstrated by using various combinations of reactants and reagents.
T. Murai, F. Asai, J. Am. Chem. Soc., 2007,
129, 780-781.
Sequential addition reactions of Grignard reagents to thioformamides give
tertiary amines in an efficient manner. The addition of different Grignard
reagents can be accomplished by using one equivalent of arylmagnesium reagent in
the first step followed by alkyl, alkenyl, aryl, or alkynyl reagents to afford
the corresponding amines in good to high yields.
T. Murai, K. Ui, Narengerile, J. Org. Chem., 2009,
74, 5703-5706.
A mild, versatile, copper-catalyzed three-component coupling of organoindium
reagents with imines and acid chlorides provides α-substituted amides
or N-protected amines in a single step with the sole byproduct being
indium trichloride.
D. A. Black, B. A. Arndtsen, Org. Lett.,
2006,
8, 1991-1993.
Highly regioselective and efficient Heck reactions of aryl triflates with N-acyl-N-vinylamines
were achieved using Pd2(dba)3, dppf, and diethylisopropylamine in dioxane. The coupling products easily
underwent acidic hydrolysis to the corresponding aryl methyl ketones or in situ
hydrogenation in the presence of (Ph3P)3RhCl under a
hydrogen atmosphere to provide the N-acyl derivatives of benzylic amines.
A. L. Hansen, T. Skydstrup, J. Org. Chem., 2005,
70, 5997-6003.
