Synthesis 2012; 44(10): 1526-1534
DOI: 10.1055/s-0031-1290815
special topic
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Aerobic Methyl/Methylene Oxygenation and C–H Formylation with a DABCO–DMSO System for the Synthesis of Carbonyl Indoles and Pyrroles

Yi-Feng Wang
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371 Singapore, Singapore , Fax: +65(6791)1961   Email: shunsuke@ntu.edu.sg
,
Feng-Lian Zhang
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371 Singapore, Singapore , Fax: +65(6791)1961   Email: shunsuke@ntu.edu.sg
,
Shunsuke Chiba*
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371 Singapore, Singapore , Fax: +65(6791)1961   Email: shunsuke@ntu.edu.sg
› Author Affiliations
Further Information

Publication History

Received: 17 February 2012

Accepted after revision: 09 March 2012

Publication Date:
20 April 2012 (online)

Abstract

Copper-catalyzed aerobic methyl/methylene oxygenation of substituted indoles and pyrroles was developed using 1,4-diazabicyclo[2.2.2]octane (DABCO) as an additive in dimethyl sulfoxide (DMSO). Similar aerobic catalytic conditions could also be utilized for direct C–H formylation of C(3) on indoles and C(2) on pyrroles.

Supporting Information

 
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