Acid-catalyzed ortho-alkylation of anilines with styrenes: an improved route to chiral anilines with bulky substituents.
[reaction: see text] Reaction of para-substituted anilines with styrene derivatives at elevated temperatures, when catalyzed by CF3SO3H, results in highly chemoselective ortho-alkylation of the aniline. When R = H, dialkylation can be achieved by varying the ratio of styrene to aniline. Several different substituted anilines and styrenes were examined, and good yields (42-87%) were obtained, except in the case where electron-withdrawing substituents are present on the styrene.
Cherian
Anna E
AE
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.
Domski
Gregory J
GJ
Rose
Jeffrey M
JM
Lobkovsky
Emil B
EB
Coates
Geoffrey W
GW