Categories: C-Cl Bond Formation >
Synthesis of benzyl chlorides
Recent Literature
A rapid, selective, and high-yielding chlorination of benzylic alcohols in the
presence of 2,4,6-trichloro-1,3,5-triazine and dimethyl sulfoxide takes 10 to 40
minutes. The neutral reaction conditions are compatible with substrates bearing
acid-labile functional groups. Both competitive intramolecular and
intermolecular reactions for benzyl alcohols in the presence of aliphatic
alcohols indicate high selectivity.
L. Sun, G. Peng, H. Niu, Q. Wang, C. Li, Synthesis, 2008,
3919-3924.
An efficient InCl3-catalyzed reaction of secondary, tertiary and
benzylic alcohols with chlorodimethylsilane in the presence of benzil gave
the corresponding organic chlorides under mild conditions. In the absence of
benzil, the reducing products through dehydroxyhydration were obtained.
M. Yasuda, S. Yamasaki, Y. Onishi, A. Baba, J. Am. Chem. Soc.,
2004,
126, 7186-7187.
The Use of Bromotrichloromethane in Chlorination Reactions
S. G. Newman, C. S. Bryan, D. Perez, M. Lautens, Synthesis, 2011,
342-346.
An indium(III) hydroxide-catalyzed reaction of carbonyls and
chlorodimethylsilane afforded the corresponding deoxygenative chlorination
products. Ester, nitro, cyano, or halogen groups were not affected during
the reaction course. Typical Lewis acids such as TiCl4, AlCl3,
and BF3ˇOEt2 showed no catalytic activity. The
reaction mechanism is discussed.
Y. Onishi, D. Ogawa, M. Yasuda, A. Baba, J. Am. Chem. Soc., 2002,
124, 13690-13691.
The reaction of alcohols and β-amino alcohols with
2,4,6-trichloro[1,3,5]triazine and N,N-dimethylformamide in methylene
chloride at room temperature gave the corresponding chlorides, and with NaBr
gave the corresponding bromides in high yields.
L. de Luca, G. Giacomelli, A. Porcheddu, Org. Lett., 2002,
4, 553-555.
The regio- and stereoselective aminochlorination of α,β-unsaturated ketones
with N,N-dichloro-p-toluenesulfonamide (4-TsNCl2) and
CuOTf as catalyst provides an easy access to
vicinal haloamino ketones, with excellent regioselectivity and good yields.
Aromatic and aliphatic enones give opposite regioselectivity.
D. Chen, C. Timmons, S. Chao, G. Li, Eur. J. Org. Chem., 2004,
3097-3101.
