Synthesis 2020; 52(08): 1231-1238
DOI: 10.1055/s-0039-1690693
special topic
© Georg Thieme Verlag Stuttgart · New York

Annulation of Indoles with 1,n-Dibromoalkanes by a Pd(II)-Catalyzed and Norbornene-Mediated Reaction Cascade

Michael Henkel
,
This project was supported by the Deutsche Forschungsgemeinschaft (BA 1372/19-1) and by the Technische Universität München (TUM) Graduate School.
Further Information

Publication History

Received: 30 August 2019

Accepted after revision: 16 September 2019

Publication Date:
02 October 2019 (online)


Dedicated to Professor Mark Lautens on the occasion of his 60th birthday

Published as part of the Special Topic Domino C–H Functionalization Reaction/Cascade Catalysis

Abstract

Employing 1,3-dibromopropane, 1,4-dibromobutane, and 1,5-dibromopentane as biselectrophiles, the annulation of indoles was probed in the presence of PdCl2(MeCN)2 as a catalyst and norbornene as a transpositional ligand. Ring formation to a five-membered ring was observed at positions C2 and N, while annulation of a six-membered ring occurred at positions C2 and C3. The latter cascade process was successfully applied to the direct synthesis of 1,2,3,4-tetrahydrocarbazoles from indoles (11 examples, 31–68% yield). Seven-membered-ring annulation was feasible by an initial coupling at positon C2 followed by alkylation at C3.

Supporting Information

Primary Data

 
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