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Synfacts 2009(1): 0015-0015
DOI: 10.1055/s-0028-1087461
DOI: 10.1055/s-0028-1087461
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Ti-Catalyzed Synthesis of Indolines
P. Wipf*, J. P. Maciejewski
University of Pittsburgh, USA
Further Information
Publication History
Publication Date:
18 December 2008 (online)
![](https://www.thieme-connect.de/media/synfacts/200901/lookinside/thumbnails/10.1055-s-0028-1087461-1.jpg)
Significance
Reported is a titanocene(III) chloride catalyzed radical annulation to form indolines and azaindolines via a reductive cyclization of epoxides tethered to substituted anilines and amino-pyridines. In situ prepared titanocene(III) chloride was used to generate reactive radical intermediates from the epoxide. From the range of substituents investigated, alkyl-substituted substrates afforded modest to good yields, electron-rich substrates gave low yields and electron-deficient substrates afforded the cyclized product in good yields.