Palladium-Catalyzed ortho-Selective C-H Chlorination of Benzamide Derivatives under Anodic Oxidation Conditions

Miki Konishi, Kazuya Tsuchida, Katsuya Sano, Takuya Kochi, Fumitoshi Kakiuchi

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)8716-8724
Number of pages9
JournalJournal of Organic Chemistry
Volume82
Issue number16
DOIs
Publication statusPublished - 2017 Aug 18

ASJC Scopus subject areas

  • Organic Chemistry

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