Categories: C-C Bond Formation > Chains >
Synthesis of substituted alkanes
Name Reactions
Recent Literature
A slow and regular addition of primary alkyl and aryl Grignard reagent
enables a high-yielding copper-catalyzed alkylation with alkyl bromides in the
absence of ligands. With secondary and
tertiary alkyl Grignard reagents, the presence of benzonitrile as a very simple
ligand is sufficent. A copper-catalyzed alkylation of organolithium compounds
was also studied.
G. Cahiez, O. Gager, J. Buendia, Synlett, 2010,
299-303.
A Pd-NHC catalytic system has been developed, that is capable of
cross-coupling various unactivated, primary bromides and alkyl organozinc
reagents in high yield at room temperature.
N. Hadei, E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, Org. Lett.,
2005,
7, 3805-3807.
The use of 2% Pd2(dba)3/8% PCyp3/NMI in
THF/NMP at 80°C achieves the cross-coupling of a range of
β-hydrogen-containing primary alkyl iodides, bromides, chlorides, and
tosylates with an array of alkyl-, alkenyl-, and arylzinc halides. This
method tolerates various functional groups.
J. Zhou, G. C. Fu, J. Am. Chem. Soc.,
2003,
125, 12527-12530.
In stereoconvergent, arylamine-directed alkyl-alkyl Suzuki cross-coupling
reactions, structure-enantioselectivity studies are consistent with the nitrogen,
not the aromatic ring, serving as the primary site of coordination of the
arylamine to the catalyst.
Z. Lu, A. Wilsily, G. C. Fu, J. Am. Chem. Soc., 2011,
133, 8154-8157.
Screening of a 15-member library of phosphaadamantane ligands has allowed
for the rapid determination of the most suitable ligand for facilitating
Suzuki-type couplings of alkyl halides or tosylates containing β-hydrogens
with either boronic acids or alkylboranes.
T. Brenstrum, D. A. Gerristma, G. M. Adjabeng, C. S. Frampton, J. Britten,
A. J. Robertson, J. McNulty, A. Capretta, J. Org. Chem., 2004,
69, 7635-7639.
A rhodium-catalyzed methylenation-hydrogenation cascade process allows the
homologation of carbonyl compounds to alkanes in high yields.
H. Lebel, C. Ladjel, J. Org. Chem., 2005,
70, 10159-10161.
