Regioselective alkenylation of aromatic ketones with alkenylboronates using a RuH2(CO)(PPh3)3 catalyst via carbon - Hydrogen bond cleavage

Satoshi Ueno, Naoto Chatani, Fumitoshi Kakiuchi

Research output: Contribution to journalArticle

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Abstract

(Chemical Equation Presented) The ruthenium-catalyzed alkenylation of C-H bonds with alkenylboronates has been explored for a series of aromatic ketones. The coupling reaction of pivalophenone (1) with 2-isopropenyl-5,5-dimethyl[1,3, 2]dioxaborinane (2) gave the corresponding isopropenylation product in 73% yield. In the case of the reaction of a sterically congested alkenylboronate, such as 2-methylpropenylboronate (8), the yield was decreased slightly. When β-styrylboronates were used, the corresponding coupling products were obtained in good yields. The reaction of acetophenone with α- styrylboronate afforded the corresponding 1:1 coupling product, exclusively.

Original languageEnglish
Pages (from-to)3600-3602
Number of pages3
JournalJournal of Organic Chemistry
Volume72
Issue number9
DOIs
Publication statusPublished - 2007 Apr 27

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Alkenylation
Ruthenium
Carbon Monoxide
Ketones
Hydrogen bonds
Carbon
Catalysts
acetophenone

ASJC Scopus subject areas

  • Organic Chemistry

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Regioselective alkenylation of aromatic ketones with alkenylboronates using a RuH2(CO)(PPh3)3 catalyst via carbon - Hydrogen bond cleavage. / Ueno, Satoshi; Chatani, Naoto; Kakiuchi, Fumitoshi.

In: Journal of Organic Chemistry, Vol. 72, No. 9, 27.04.2007, p. 3600-3602.

Research output: Contribution to journalArticle

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abstract = "(Chemical Equation Presented) The ruthenium-catalyzed alkenylation of C-H bonds with alkenylboronates has been explored for a series of aromatic ketones. The coupling reaction of pivalophenone (1) with 2-isopropenyl-5,5-dimethyl[1,3, 2]dioxaborinane (2) gave the corresponding isopropenylation product in 73{\%} yield. In the case of the reaction of a sterically congested alkenylboronate, such as 2-methylpropenylboronate (8), the yield was decreased slightly. When β-styrylboronates were used, the corresponding coupling products were obtained in good yields. The reaction of acetophenone with α- styrylboronate afforded the corresponding 1:1 coupling product, exclusively.",
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AB - (Chemical Equation Presented) The ruthenium-catalyzed alkenylation of C-H bonds with alkenylboronates has been explored for a series of aromatic ketones. The coupling reaction of pivalophenone (1) with 2-isopropenyl-5,5-dimethyl[1,3, 2]dioxaborinane (2) gave the corresponding isopropenylation product in 73% yield. In the case of the reaction of a sterically congested alkenylboronate, such as 2-methylpropenylboronate (8), the yield was decreased slightly. When β-styrylboronates were used, the corresponding coupling products were obtained in good yields. The reaction of acetophenone with α- styrylboronate afforded the corresponding 1:1 coupling product, exclusively.

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