Categories: C-C Bond Formation > Arenes >
Synthesis of biaryls
| Synthesis of | |
| Heterobiaryls |  |
Name Reactions
|
Versatile Cross Coupling Methods: Hiyama Coupling (R-X + R'-SiR''3) Hiyama-Denmark Coupling (R-X + R-SiMe2OH) Kumada Coupling (R-X + R'-MgX) Negishi Coupling (R-X + R'-ZnX) Stille Coupling (R-X + R'-SnR''3) Suzuki Coupling (R-X + R'-BY3) |
Pschorr Reaction
Recent Literature
Aryltriethoxysilanes were cross-coupled with aryl bromides in high yield in
the presence of a palladium catalyst and aqueous sodium hydroxide. Addition of P(OiPr)3
helps to prevent the precipitation of palladium black.
M. Murata, R. Shimazaki, S. Watanabe, Y. Masuda, Synthesis,
2001, 2231-2233.
Room-temperature Ni(0)-catalyzed cross-coupling reactions of deactivated
aryl chlorides with arylboronic acids with inexpensive triphenylphosphine as
ligand have been accomplished in good to excellent yields. Highly active
nickel catalysts were obtained through the reduction of air-stable Ni(PPh3)2Cl2
with n-BuLi in the presence of an aryl chloride.
Z.-Y. Tang, Q.-S. Hu, J. Org. Chem., 2006,
71, 2167-2169.
Nickel-catalyzed cross-coupling of Grignard reagents with aryl fluorides or
chlorides can be achieved efficiently in the presence of a new
triarylphosphine ligand. The high reactivity and the unique chemoselectivity
of the catalysis have been attributed to synergy of nickel and magnesium
atoms preorganized on the ligand.
N. Yoshikai, H. Mashima, E. Nakamura, J. Am. Chem. Soc.,
2005,
127, 17978-17979.
Palladium-catalyzed Heck and Suzuki coupling reactions of arenediazonium
salts were performed at room temperature, without added base, under aerobic
conditions using a thiourea based C2-symmetric ligand. The
reactions produced product in 4 h in good yield.
M. Dai, B. Liang, C. Wang, J. Chen, Z. Yang, Org. Lett., 2004,
6, 221-224.
A suzuki cross-coupling reaction of aryltrimethylammonium triflates based on
an IMes·Ni(0) catalyst system tolerates a wide range of electron-withdrawing
and electron-donating substituents on both coupling partners. This
methodology constitutes a novel, mild method to activate anilines for
metal-catalyzed cross-coupling reactions.
S. B. Blakey, D. W. C. MacMillan, J. Am. Chem. Soc., 2003,
125, 6046-6047.
Air-Stable PinP(O)H as Preligand for Palladium-Catalyzed Kumada Couplings of
Unactivated Tosylates
L. Ackermann, A. Althammer, Org. Lett.,
2006,
8, 3457-3460.
A range of biaryl compounds can be efficiently prepared in high yields by a
palladium-catalyzed cross-coupling reaction between ortho-substituted
triarylindium reagents and aryl halides. The triarylindium reagents are prepared
by directed ortho-lithiation and transmetallation to indium from the
corresponding benzene derivatives.
M. A. Pena, J. P. Sestelo, L. A. Sarandeses, J. Org. Chem., 2007,
72, 1271-1275.
Sterically demanding 1,3-dialkyl-3,4,5,6-tetrahydropyrimidinium salts as NHC
precursors in combination with palladium acetate provided active catalysts for
the cross-coupling of aryl chlorides and bromides under mild conditions. The
catalytic system was applied to the Heck, Suzuki and benzaldehyde coupling
reactions.
I. Özdemir, S. Demir, B. Çetinkaya, Tetrahedron, 2005,
61, 9791-9798.
The mild cross-coupling reaction of alkyl- and arylmanganese reagents with
o-chloro- or o-bromoaryl ketones give substituted ketones in high
yields with excellent chemoselectivity.
G. Cahiez, D. Luart, F. Lecomte, Org. Lett.,
2004,
6, 4395-4398.
The ortho-arylation of aromatic ketones with arylboronates using RuH2(CO)(PPh3)3
as a catalyst was conducted in pinacolone. This solvent dramatically
suppressed the competing reduction of the aromatic ketones and, as a result,
ortho-arylated products were obtained in high yield. The mechanism is
discussed.
F. Kakiuchi, Y. Matsuura, S. Kan. N. Chatani, J. Am. Chem. Soc.,
2005,
127, 5936-5945.
A direct Pd-catalyzed arylation reaction for the intramolecular formation of
biaryl compounds using a novel phosphine ligand offers enhanced catalytic
activity for transformations of previously unreactive substrates.
L.-C. Campeau, M. Parisien, M. Leblanc, K. Fagnou, J. Am. Chem. Soc.,
2004,
126, 9186-9187.
