Categories: C-Cl Bond Formation >
Synthesis of aryl chlorides
Name Reactions
Recent Literature
N-Halosuccinimides are efficiently activated in
trifluoromethanesulfonic acid and BF3-H2O, allowing
the halogenations of deactivated aromatics. BF3-H2O is
more economic, easy to prepare, nonoxidizing, and offers sufficiently high
acidity.
G. K. S. Prakash, T. Mathew, D. Hoole, P. M. Esteves, Q. Wang, G. Rasul, G.
A. Olah, J. Am. Chem. Soc.,
2004,
126, 15570-15776.
A mild, efficient, Cu(I)-catalyzed method for the synthesis of aryl chlorides
from arylboronic acids is particularly useful for the conversion of
electron-deficient arylboronic acids to aryl chlorides, a transformation that is
inefficient in the absence of Cu catalysis.
H. Wu, J. Hynes, Jr., Org. Lett., 2010,
12, 1192-1195.
A mild and metal-free method for the chlorodeboronation of
organotrifluoroborates using trichloroisocyanuric acid (TCICA) converts aryl-,
heteroaryl-, alkenyl-, alkynyl-, and alkyltrifluoroborates into the
corresponding chlorinated products in good yields. This method tolerates a broad
range of functional groups.
G. A. Molander, L. N. Cavalcanti, J. Org. Chem., 2011,
76, 7195-7203.
A mild palladium-catalyzed, regioselective chlorination, bromination, and
iodination of arene C-H bonds using N-halosuccinimides as oxidants is
described. These transformations can provide products that are complementary
to those obtained via conventional electrophilic aromatic substitution
reactions.
D. Kalyani, A. R. Dick, W. Q. Anani, M. S. Sanford, Org. Lett.,
2006,
8, 2523-2526.
ridium-catalyzed borylation of 1,3-disubstituted arenes with B2pin2,
followed by reaction of the boronic ester with copper(II) bromide or chloride
converts arylboronic esters to the corresponding meta-halogenated aryl
halides. Various functional groups, such as alkoxy, alkyl, halogen, nitrile,
ester, amide, and pivaloyl and TIPS-protected alcohols, are tolerated.
J. M. Murphy, X. Liao, J. F. Hartwig, J. Am. Chem. Soc., 2007,
129, 15434-15435.
A facile Pd-catalyzed conversion of aryl and vinyl triflates allows convenient
access to various aryl, heteroaryl, and vinyl halides in good to excellent
yields and with greatly simplified conditions relative to our previous report.
J. Pan, X. Wang, Y. Zhang, S. L. Buchwald, Org. Lett., 2011,
13, 4974-4976.
