Acid-catalyzed ortho-alkylation of anilines with styrenes: an improved route to chiral anilines with bulky substituents |
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Authors: | Cherian Anna E Domski Gregory J Rose Jeffrey M Lobkovsky Emil B Coates Geoffrey W |
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Institution: | Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA. |
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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. |
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