Categories: C-C Bond Formation > Arenes >
Benzylation, synthesis of diarylmethanes
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Recent Literature
A highly efficient secondary benzylation procedure of nucleophiles (arenes,
heteroarenes, alcohols, thiols, amides) with benzylic alcohols afforded the corresponding benzylated
products in moderate to excellent yields in the presence of a high-valent heterobimetallic complex [Ir2(COD)2(SnCl3)2(Cl)2(μ-Cl)2] as the catalyst.
S. Podder, J. Choudhury, S. Roy, J. Org. Chem., 2007,
72, 3129-3132.
The palladium catalysed cross-coupling of various benzylic carbonates with
arylboronic acids gave the corresponding diarylmethanes in high yields. The
catalyst is generated in situ from [Pd(η3-C3H5)Cl]2
and 1,5-bis(diphenylphosphino)pentane (DPPPent).
R. Kuwano, M. Yokogi, Org. Lett., 2005,
7, 945-947.
Suzuki-Miyaura cross-coupling of benzylic phosphates with arylboronic acids
using a simple catalytic system of palladium(II) acetate and
triphenylphosphine with either potassium phosphate or potassium carbonate as
the base and toluene as the solvent at 90°C allows the preparation of a
series of structurally diverse diarylmethanes.
M. McLaughlin, Org. Lett.,
2005,
7, 4875-4878.
Coupling of sterically hindered aryl and activated alkyl chlorides bearing
β-hydrogens has been successfully achieved by using N-heterocyclic
carbene (NHC)Pd-carboxylate complexes as catalysts.
R. Singh, M. S. Viciu, N. Kramareva, O. Navarro, S. P. Nolan, Org. Lett.,
2005,
7, 1829-1832.
A new, reusable Pd/MgLa mixed oxide catalyst has been applied successfully
in the Suzuki-Miyaura cross-coupling reaction of aryl halides as well as
benzylic bromide with boronic acids in ethanol. The catalyst is air stable,
can be stored and handled under an ambient atmosphere and after the reaction
it can be recovered by simple filtration and reused without significant loss
of activity.
A. Cwik, Z. Hell, F. Figueras, Org. Biomol. Chem., 2005,
3, 4307-4309.
Palladium catalyzed Suzuki-Miyaura coupling with aryl chlorides using a
bulky phenanthryl N-heterocyclic carbene ligand
C. Song, Y. Ma, Q. Chai, C. Ma, W. Jiang, M. B. Andrus, Tetrahedron, 2005,
61, 7438-7446.
A combination of copper chloride, triethyl phosphite, and tetrabutylammonium
iodide is a very efficient catalytic system for cross-coupling reaction of
arylmagnesium halides with benzylic phosphates.
C. C. Kofink, P. Knochel, Org. Lett.,
2006,
8, 4121-4124.
The superacid-catalyzed reaction of various olefinic amines and
related compounds with benzene gives addition products in good yields. The
formation of reactive, dicationic electrophiles is proposed.
Y. Zhang, A. McElrea, G. V. Sanchez, Jr., D. Do, A. Gomez, S. L . Aguirre, R. Rendy, D. A. Klumpp, J. Org. Chem., 2003,
68, 5119-5122.
The reaction of different functionalised organolithium compounds prepared by
DTBB-catalysed lithiation of isochromane, phthalane, 2,3-dihydrobenzofuran
and 1-chloro-3,3-diethoxypropane with an equimolecular amount of zinc
bromide, followed by reaction with an aryl or an alkenyl bromide in the
presence of a palladium catalyst gives the expected cross-coupling products.
M. Yus, J. Gomis, Eur. J. Org. Chem., 2002, 1989-1995.
A palladium-catalyzed cross-coupling reaction between acetates of
Baylis-Hillman adducts and organosilanes in PEG as solvent is described.
G. W. Kabalka, J. Org. Chem., 2005,
70, 9207-9210.
