Regioselective C-H bond cleavage/alkyne insertion under ruthenium catalysis

Yuto Hashimoto, Koji Hirano, Tetsuya Satoh, Fumitoshi Kakiuchi, Masahiro Miura

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62 Citations (Scopus)

Abstract

The ruthenium-catalyzed coupling reactions of benzamides with alkynes in the presence of acetic acid as a promoter smoothly proceeded regio- and stereoselectively through a directed C-H bond cleavage to produce the corresponding ortho-alkenylated products. Phenylpyrazoles and related substrates also underwent a similar coupling to give dialkenylated products selectively. Several competitive experiments were performed to obtain mechanistic insight into both the mono- and dialkenylation reactions.

Original languageEnglish
Pages (from-to)638-646
Number of pages9
JournalJournal of Organic Chemistry
Volume78
Issue number2
DOIs
Publication statusPublished - 2013 Jan 18

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ASJC Scopus subject areas

  • Organic Chemistry

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