Synthesis 2018; 50(07): 1521-1526
DOI: 10.1055/s-0037-1609152
paper
© Georg Thieme Verlag Stuttgart · New York

Aminocarbonylation of N-Containing Heterocycles with Aromatic Amines Using Mo(CO)6

Marius Mamone
a  Institut Curie, PSL Research University, CNRS, INSERM, UMR9187-U1196, 91405 Orsay, France
,
Jessy Aziz
a  Institut Curie, PSL Research University, CNRS, INSERM, UMR9187-U1196, 91405 Orsay, France
,
Julie Le Bescont
a  Institut Curie, PSL Research University, CNRS, INSERM, UMR9187-U1196, 91405 Orsay, France
b  Université Paris Sud, Université Paris-Saclay, 91405 Orsay, France   Email: sandrine.piguel@u-psud.fr
,
Sandrine Piguel*
a  Institut Curie, PSL Research University, CNRS, INSERM, UMR9187-U1196, 91405 Orsay, France
b  Université Paris Sud, Université Paris-Saclay, 91405 Orsay, France   Email: sandrine.piguel@u-psud.fr
› Author Affiliations
French program ‘Investissement d’Avenir – Institut Carnot’ managed by the National Research Agency (ANR-11-CARN-008-01).
Further Information

Publication History

Received: 13 December 2017

Accepted after revision: 13 December 2017

Publication Date:
18 January 2018 (online)


Abstract

We describe herein the palladium-catalyzed aminocarbonylation of nitrogen-containing heterocycles with aniline derivatives using molybdenum hexacarbonyl as a CO solid source, expanding the scope of the limited examples. This method is compatible with a variety of substitutions on the aniline moiety. The simple reaction conditions include easily available Pd(dppf)Cl2 catalyst, DBU as base in DMF at 120 °C for 3 hours in sealed tube thereby leading to the isolation of 21 compounds with yields ranging from 18 to 82%. We also show that double aminocarbonylation reactions are possible in satisfactory yields regarding both coupling partners.

Supporting Information

 
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