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 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.

