Synthesis 2003(15): 2317-2320  
DOI: 10.1055/s-2003-41060
PAPER
© Georg Thieme Verlag Stuttgart · New York

Convenient N-Formylation of Secondary Amines: KF-Al2O3-Promoted Synthesis of Formamide Derivatives via Dichlorocarbene Generated from Chloroform

Masatoshi Miharaa, Yoshio Ishino*a, Satoshi Minakatab, Mitsuo Komatsu*b
a Osaka Municipal Technical Research Institute, Morinomiya 1-6-50, Joto-ku, Osaka 536-8553, Japan
Fax: +81(6)69638049; e-Mail: ishino@omtri.city.osaka.jp;
b Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan
Fax: 81(6)68797402; e-Mail: komatsu@chem.eng.osaka-u.ac.jp;
Further Information

Publication History

Received 9 June 2003
Publication Date:
23 September 2003 (online)

Abstract

The treatment of secondary amines with chloroform in the presence of KF-Al2O3 in acetonitrile brought about highly facile and efficient N-formylation to give the corresponding formamides in good to excellent yields. The N-formylation reaction not only involves mild conditions, simple operations and high yields but high chemoselectivity as well.