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

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40 Citations (Scopus)

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

ASJC Scopus subject areas

  • Organic Chemistry

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