Acid-Catalyzed ortho-Alkylation of Anilines with Styrenes:  An Improved Route to Chiral Anilines with Bulky Substituents

Acid-Catalyzed ortho-Alkylation of Anilines with Styrenes:  An Improved Route to Chiral Anilines with Bulky Substituents

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 ani...

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Veröffentlicht in:Organic letters 2005-11, Vol.7 (23), p.5135-5137
Hauptverfasser: Cherian, Anna E, Domski, Gregory J, Rose, Jeffrey M, Lobkovsky, Emil B, Coates, Geoffrey W
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container_issue 23
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container_title Organic letters
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creator Cherian, Anna E
Domski, Gregory J
Rose, Jeffrey M
Lobkovsky, Emil B
Coates, Geoffrey W
description 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.
doi_str_mv 10.1021/ol051916j
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title Acid-Catalyzed ortho-Alkylation of Anilines with Styrenes:  An Improved Route to Chiral Anilines with Bulky Substituents
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