One-Pot Synthesis of Tertiary Amides from Organic Trichlorides through Oxygen Atom Incorporation from Air by Convergent Paired Electrolysis

Zhongli Luo; Kenji Imamura; Yoshihito Shiota; Kazunari Yoshizawa; Yoshio Hisaeda; Hisashi Shimakoshi

doi:10.1021/acs.joc.1c00161

One-Pot Synthesis of Tertiary Amides from Organic Trichlorides through Oxygen Atom Incorporation from Air by Convergent Paired Electrolysis

J Org Chem. 2021 Apr 16;86(8):5983-5990. doi: 10.1021/acs.joc.1c00161. Epub 2021 Apr 2.

Authors

Zhongli Luo¹, Kenji Imamura², Yoshihito Shiota², Kazunari Yoshizawa², Yoshio Hisaeda¹, Hisashi Shimakoshi¹

Affiliations

¹ Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Nishi-ku, Motooka, Fukuoka 819-0395, Japan.
² Institute for Materials Chemistry and Engineering, Kyushu University, Nishi-ku, Motooka, Fukuoka 819-0395, Japan.

PMID: 33797908
DOI: 10.1021/acs.joc.1c00161

Abstract

A convergent paired electrolysis catalyzed by a B₁₂ complex for the one-pot synthesis of a tertiary amide from organic trichlorides (R-CCl₃) has been developed. Various readily available organic trichlorides, such as benzotrichloride and its derivatives, chloroform, dichlorodiphenyltrichloroethane (DDT), trichloro-2,2,2-trifluoroethane (CFC-113a), and trichloroacetonitrile (CNCCl₃), were converted to amides in the presence of tertiary amines through oxygen incorporation from air at room temperature. The amide formation mechanism in the paired electrolysis, which was mediated by a cobalt complex, was proposed.