TY - JOUR
T1 - One-Pot Synthesis of Tertiary Amides from Organic Trichlorides through Oxygen Atom Incorporation from Air by Convergent Paired Electrolysis
AU - Luo, Zhongli
AU - Imamura, Kenji
AU - Shiota, Yoshihito
AU - Yoshizawa, Kazunari
AU - Hisaeda, Yoshio
AU - Shimakoshi, Hisashi
N1 - Funding Information:
This study was partially supported by a Grant-in-Aid for Scientific Research (B) (JP19H02735) from the Japan Society for the Promotion of Science (JSPS). Part of the study was performed under the Cooperative Research Program of “Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials” (20203024) and a grant from the Nippon Sheet Glass Foundation (HAKF541800).
Publisher Copyright:
© 2021 American Chemical Society. All rights reserved.
PY - 2021/4/16
Y1 - 2021/4/16
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.joc.1c00161
DO - 10.1021/acs.joc.1c00161
M3 - Article
AN - SCOPUS:85104928706
SN - 0022-3263
VL - 86
SP - 5983
EP - 5990
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 8
ER -