5 years ago

Palladium-Catalyzed Regioselective Synthesis of 3-Arylindoles from N-Ts-Anilines and Styrenes

Palladium-Catalyzed Regioselective Synthesis of 3-Arylindoles from N-Ts-Anilines and Styrenes
Tae Yun Ko, Young Ho Jang, So Won Youn
A Pd-catalyzed intermolecular oxidative annulation between N-Ts-anilines and styrenes was developed. This method offers a straightforward and robust approach to a wide range of 3-arylindoles using readily available starting materials with good functional-group tolerance and high regioselectivity and efficiency. Further elaboration of the products obtained from this process provided access to highly functionalized and structurally diverse indoles, for example, 3-(indol-3-yl)carbazoles, 1,9-dihydropyrrolo-[2,3-b]carbazoles, and 3′-aryl-3,5′-biindoles. Hello from the other side: A Pd-catalyzed intermolecular oxidative annulation for one-pot C−C/C−N bond formation was developed. In contrast to the opposite regioselectivity pattern of related methods, this method offers facile access to the synthetically valuable 3-arylindoles, which were previously inaccessible from styrenes and anilines, with high efficiency and excellent regioselectivity.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201702205

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