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Synthesis 2011(8): 1227-1232  
DOI: 10.1055/s-0030-1259978
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Pd/C-Catalyzed Reductive Formylation of Indoles and Quinolines Using Formic Acid

Aditya Kulkarni, Ryan Gianatassio, Béla Török*
Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Blvd., Boston, MA 02125, USA
Fax: +1(617)2876030; e-Mail: bela.torok@umb.edu;
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Publication History

Received 6 January 2011
Publication Date:
30 March 2011 (online)

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Abstract

A two-step, one-pot domino reaction methodology was developed to synthesize a variety of N-formylindolines and N-formyltetrahydroquinolines from the corresponding indoles and quinolines. In the first step, the heterocyclic compounds are reduced to the corresponding dihydro or tetrahydro products by a Pd/C-catalyzed transfer hydrogenation using formic acid as a hydrogen donor. In the second step, nitrogen is formylated by formic acid to afford the final products in very good isolated yields.

Key words

catalytic transfer hydrogenation - indoles - quinolines - formylation - domino reaction

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See the spectroscopic data for more information.