3 years ago

Catalytic Reductive Synthesis and Direct Derivatization of Unprotected Aminoindoles, Aminopyrroles, and Iminoindolines

Catalytic Reductive Synthesis and Direct Derivatization of Unprotected Aminoindoles, Aminopyrroles, and Iminoindolines
Jens Weweler, Jan Streuff, Leonardus H. Leijendekker, Tobias M. Leuther
A titanium(III)-catalyzed radical cyclization to unprotected 3-aminoindoles, 3-aminopyrroles, or 3-iminoindolines is reported. The reaction is non-hazardous, scalable, and allows facile isolation of the free products by extraction. The method is demonstrated on a large substrate scope and it further allows the direct installation of various nitrogen protecting groups or the synthesis of building blocks for peptide chemistry in a single sequence. Fused bisindoles can be directly accessed from the cyclization products. Free at last: A titanium(III)-catalyzed reductive cyclization allows the safe and convenient synthesis of unprotected aminoindoles, aminopyrroles, and other aminated heterocycles. The novel cyclization approach further enables the direct functionalization at the nitrogen atom via various coupling methods in a single sequence.

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

DOI: 10.1002/anie.201702310

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