Synthesis 2014; 46(20): 2727-2733
DOI: 10.1055/s-0034-1379208
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

Pd(II)/Bu4NBr/DMSO Catalytic System for Practical Synthesis of Indoles and Pyrroles from Imines through Aerobic Dehydrogenative Cyclization

Wei Wen Tan
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore   Fax: +6569711961   Email: [email protected]
,
Xiaoya Hou
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore   Fax: +6569711961   Email: [email protected]
,
Naohiko Yoshikai*
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore   Fax: +6569711961   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 17 May 2014

Accepted after revision: 03 September 2014

Publication Date:
25 September 2014 (online)


Abstract

N-Aryl- and N-allylimines derived typically from substituted acetophenones undergo palladium(II)-catalyzed dehydrogenative cyclization reactions in the presence of tetrabutylammonium bromide and molecular oxygen in DMSO to afford indole and pyrrole derivatives, respectively, in moderate to good yields. The reactions are operationally simple and can be readily performed on multigram scales (up to 55 mmol).

Supporting Information

 
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