title: Acid-catalyzed ortho-alkylation of anilines with styrenes: an improved route to chiral anilines with bulky substituents.
abstract: [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.
authors.affiliation: Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.
authors.forename: Anna E
authors.initials: AE
authors.lastname: Cherian
authors.forename: Gregory J
authors.initials: GJ
authors.lastname: Domski
authors.forename: Jeffrey M
authors.initials: JM
authors.lastname: Rose
authors.forename: Emil B
authors.initials: EB
authors.lastname: Lobkovsky
authors.forename: Geoffrey W
authors.initials: GW
authors.lastname: Coates