Categories: C-C Bond Formation > Amines, Arenes >
Synthesis of benzylamines
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Recent Literature
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.
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.
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.
