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

Masatoshi Mihara; Yoshio Ishino; Satoshi Minakata; Mitsuo Komatsu

doi:10.1055/s-2003-41060

PAPER

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

Masatoshi Mihara^a, Yoshio Ishino*^a, Satoshi Minakata^b, 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;

Abstract

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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.

Keywords

potassium fluoride - formylation - amines - amides - carbenes

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References

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