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

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

Research output: Contribution to journalArticle

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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Benzamides
Alkynes
Ruthenium
Acetic Acid
Catalysis
Substrates
Experiments

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Regioselective C-H bond cleavage/alkyne insertion under ruthenium catalysis. / Hashimoto, Yuto; Hirano, Koji; Satoh, Tetsuya; Kakiuchi, Fumitoshi; Miura, Masahiro.

In: Journal of Organic Chemistry, Vol. 78, No. 2, 18.01.2013, p. 638-646.

Research output: Contribution to journalArticle

Hashimoto, Yuto ; Hirano, Koji ; Satoh, Tetsuya ; Kakiuchi, Fumitoshi ; Miura, Masahiro. / Regioselective C-H bond cleavage/alkyne insertion under ruthenium catalysis. In: Journal of Organic Chemistry. 2013 ; Vol. 78, No. 2. pp. 638-646.
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