Categories: C-C Bond Formation > Arenes > Biaryls >
Synthesis of heterobiaryls
Recent Literature
Highly stable and active Pd-phosphine catalysts have been found for the
Suzuki-Miyaura coupling of pyridine, pyrrole, and indole boronic acids.
These complexes are not inhibited by the presence of highly basic
aminopyridines or aminopyrimidines.
K. L. Billingsley, K. W. Anderson, S. L. Buchwald, Angew. Chem. Int. Ed.,
2006,
45, 3484-3488.
A new catalyst system for the Pd-catalyzed cross-coupling of organozinc
reagents with aryl halides permits efficient preparation of hindered
biaryls, functions effectively at low levels of catalyst, and tolerates a
wide range of functional groups and heterocyclic substrates.
J. E. Milne, S. L. Buchwald, J. Am. Chem. Soc.,
2004,
126, 13028-13032.
New air-stable PdCl2{PR2(Ph-R')}2 complexes,
readily prepared from commercial reagents, exhibit unique efficiency as
catalysts for the Suzuki-Miyaura coupling reactions of a variety of
heteroatom-substituted heteroaryl chlorides with a diverse range of aryl/heteroaryl
boronic acids.
A. S. Guram, X. Wang, E. E. Bunel, M. M. Faul, R. D. Larsen, M. J. Martinelli, J. Org. Chem., 2007,
72, 5104-5112.
New air-stable palladium phosphine complexes represent simple, general, and
efficient catalysts for the Suzuki-Miyaura cross-coupling of aryl halides
including five-membered heteroaryl halides and heteroatom-substituted
six-membered heteroaryl chlorides with a various arylboronic acids.
A. S. Guram, A. O. King, J. G. Allen, X. Wang, L. B. Schenkel, J. Chan, E.
E. Bunel, M. M. Faul, R. D. Larsen, M. J. Martinelli, P. J. Reider, Org.
Lett.,
2006,
8, 1787-1789.
Air-stable and easily accessible PinP(O)H enables highly efficient
palladium-catalyzed Kumada cross-coupling reactions of aryl tosylates. The
in situ generated catalyst proved applicable not only to electron-rich and
electron-poor carbocyclic tosylates but also to heterocyclic tosylates, such
as pyridine and quinoline derivatives.
L. Ackermann, A. Althammer, Org. Lett.,
2006,
8, 3457-3460.
C-C Coupling Reactions of Aryl Bromides and Arylsiloxanes in Water Catalyzed
by Palladium Complexes of Phosphanes Modified with Crown Ethers
I. Gordillo, E. de Jesús, C. López-Mardomingo, Org. Lett.,
2006,
8, 3517-3520.
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.
A highly efficient method for the synthesis of multisubstituted 1,2,3-triazoles
via a direct Pd-catalyzed C-5 arylation has been developed.
S. Chuprakov, N. Chernyak, A. S. Dudnik, V. Gevorgyan, Org. Lett., 2007,
9, 2333-2336.
An efficient and mild Negishi cross-coupling strategy for substituted 2,2′-bipyridines
uses tetrakis(triphenylphosphine)palladium(0) as a simple, commercially
available, and relatively inexpensive catalyst for both 2-bromo- and
2-chloropyridines.
U. Kiehne, J. Bunzen, H. Staats, A. Lützen, Synthesis, 2007,
1061-1069.
Various 5-substituted 2,2-bipyridines have been synthesized from substituted
2-chloropyridines through a modified Negishi cross-coupling reaction.
A. Lützen, M. Hapke, Eur. J. Org. Chem., 2002, 2292-2297.
Thiophene was regioselectively deprotonated by treatment with Bu3MgLi
in THF at room temperature. The lithium arylmagnesate formed was either trapped
with electrophiles or cross-coupled in a ‘one-pot’ procedure with aryl halides
under palladium catalysis.
O. Bayh, H. Awad, F. Mongin, C. Hoarau, F. Trécourt, G. Quéquiner, F. Marsais,
F. Blanco, B. Abarca, R. Ballesteros, Tetrahedron, 2005,
61, 4779-4784.
