TY - JOUR
T1 - Palladium-Catalyzed ortho-Selective C-H Chlorination of Benzamide Derivatives under Anodic Oxidation Conditions
AU - Konishi, Miki
AU - Tsuchida, Kazuya
AU - Sano, Katsuya
AU - Kochi, Takuya
AU - Kakiuchi, Fumitoshi
N1 - Funding Information:
This work was supported in part by JSPS KAKENHI grant number JP15H05839 in Middle Molecular Strategy and CREST and ACT-C from the Japan Science and Technology Agency (JST), Japan. T.K. is also grateful to the support by JSPS KAKENHI grant number 16H01040 (Precisely Designed Catalysts with Customized Scaffolding).
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/8/18
Y1 - 2017/8/18
N2 - The palladium-catalyzed ortho-selective chlorination of N-quinolinylbenzamide derivatives with hydrochloric acid was achieved under anodic oxidation conditions. The use of 5,7-dichloro-8-quinolinyl group as directing group was effective for the selective chlorination, and the reaction was applicable to benzamide derivatives bearing various functional groups. Synthesis of vismodegib was also completed using the palladium-catalyzed electrochemical C-H chlorination in two different steps.
AB - The palladium-catalyzed ortho-selective chlorination of N-quinolinylbenzamide derivatives with hydrochloric acid was achieved under anodic oxidation conditions. The use of 5,7-dichloro-8-quinolinyl group as directing group was effective for the selective chlorination, and the reaction was applicable to benzamide derivatives bearing various functional groups. Synthesis of vismodegib was also completed using the palladium-catalyzed electrochemical C-H chlorination in two different steps.
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U2 - 10.1021/acs.joc.7b01137
DO - 10.1021/acs.joc.7b01137
M3 - Article
C2 - 28758746
AN - SCOPUS:85027589030
SN - 0022-3263
VL - 82
SP - 8716
EP - 8724
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 16
ER -